Should you start a business?

It’s a big question, so I asked 50 successful entrepreneurs to share their advice on what you need to think about before you decide if you should start a business (I chimed in, too). They all answered this question:

What 3 pieces of advice would you have for someone who is wondering if they should start a business?

Their individual responses are worth reading every word of, but I was most interested to see the common themes that came up from these women across multiple disciplines. Their advice fell into 8 main categories.

Should You Start a Business? Here’s the main advice:

  1. Don’t quit your day job…yet. Ease into having a business. (Learn more about creating a career Crossfade.)
  2. Be true to you. That means trusting your gut, keeping your eyes on your own paper, being authentic, and creating a business that uniquely suits you and your strengths.
  3. Just start. Use what you have and don’t wait for perfection.
  4. Get a support network. You don’t succeed alone, so find mentors, friends, and supportive community.
  5. Serve. Your business is not about you, it’s about the people you serve. Listen to them and create for them.
  6. Think like a business owner. You’ll need to make decisions about marketing, selling, investing, etc.
  7. Be prepared to work hard. Period.
  8. Know why you’re working. Have a bigger vision and purpose than not wanting a day job.

Honorable mention categories

These were not the top rated responses, but they got enough attention and are important enough that I want to include them.

  1. Consider if you’re a self-starter.
  2. Be prepared to fail.
  3. Adapt.
  4. Embrace imperfection.
  5. Improve your relationship with money.

Keep reading for insights from some of your favorite entrepreneurs. You’ll hear from:

Abby Kerr, Anne Samoilov, April Bowles-Olin, Beth Buelow, Brandi Bernoski, Breanne Dyck, Catherine Just, Danielle Spurge, Elise Cripe, Elise Grice, Erin Loechner, Esme Wang, Farideh Ceasar, Jane Riley, Jen Carrington, Jen Hansard, Jennifer Lee, Jennifer Louden, Jenny Blake, Julie Parker, Kaniesha Grayson, Kate Swoboda, Kathleen Shannon, Kelsey Baldwin, Kyla Roma, L’Erin Alta, Laura Simms, Lauren Hooker, Lisa Congdon, Mara Glatzel, Mayi Carles, Melyssa Griffin, Michelle Ward, Molly Mahar, Nathalie Lussier, Nesha Woolery, Rachel Cole, Randi Buckley, Sally Hope, Sarah Bray, Sarah Morgan, Sarah Von Bargen, Sas Petherick, Sally Waldman, Shenee Howard, Stephanie Pollock, Susannah Conway, Tanya Geisler, Theresa Reed, Theresa Roth, and Tiffany Han.

Should You Start a Business? Things to think about as you decide:

(responses are listed in the order they were received)

Elise Blaha Cripe

Creator of Get to Work Book

1. Be prepared to work hard! 

2. Don’t worry about all the steps from beginning to end, you’ll get overwhelmed before you’ve even started! Instead, focus on the one thing you can do TODAY.

3. Get comfortable asking for help and saying “I don’t know, but I’ll find out.”

Nesha Woolery

Brand & Website Designer

1. Think about whether you have what it takes to run a successful business. The hard truth is that not everyone is cut out to be their own boss- it takes determination, motivation and a lot of self-discipline. If you have those qualities, you’ll make a great business owner. If you don’t have them, maybe you should spend some time cultivating those qualities before leaping into the world of business.

2. Don’t spontaneously leave your day job to start your own business- calculate the costs and build up your clientele first.

3. Create a business plan, but not the boring 20-page kind. Create a simple plan and simple goals for your business. It will help you stay on the track to success in your first year of self-employment.

Sarah Von Bargen

Blogging Mentor

1. Do what you say you’re doing to do. Being dependable and reliable trumps everything – skill, connections, education. I’ve worked with dozens of contractors and about 10% of them keep their word and meet deadlines. Be one of the 10%

2. Be good at one (or two) social media platforms. You don’t need to be everywhere and it’s better to be good at one thing that mediocre at five. Find out where your ideal clients are hanging out and then learn how to really excel at that platform.

3. Test your services/products before you launch them. Offer your stuff for free/super cheap in exchange for testimonials. Ask friends to help you find the bugs in your systems. You might find out that while people really want a specific service, you don’t particularly enjoy offering it!

Theresa Reed

The Tarot Lady, professional tarot reader

1. Before you dip your toes into the entrepreneurial waters, you need to spend some time doing research on YOU.  That means getting clear on whether or not you are cut out for self-employment.  I think a lot of people have this illusion that running a business is somehow glamorous or easy.  Most of the time, it’s long hours and learning to live within a feast and famine cycle!  I’ve seen many people dive in, only to fold a few years (or months) later when they discovered that it’s much trickier than it looks. You need to take some time to examine your temperament to see if self-employment is your jam…or not.

Here’s what you should be asking yourself:

  • How much money do I need to make in order to be comfortable? (Know your number!)
  • Am I okay with an uncertain income and how might this affect my household?
  • Will I be able to make enough to cover the benefits that my job offers?  If not, what measures will I take to ensure that I have the coverage I need?
  • How will I manage my schedule?
  • Am I good at time management?  If not, what do I need to change that?
  • Do I have a support system in place?
  • How comfortable am I with risk?
  • What kind of goals am I setting – and what am I going to do to reach those goals?
  • What happens if this doesn’t work out? Then what?

If you find yourself feeling confident that you have the traits to handle self-employment, get your plan in order and take that first step!

2. Get a mentor. This is SO important.  A good mentor can give you support and wise counsel as you learn to navigate the business world.  Find one that is in your niche, preferably one that has some real experience. I’m talking a long, sustainable career.  Someone who has been at their game for a long time will know what it takes to ride the ups and downs. That knowledge is priceless. If you are lucky enough to get a good mentor, you’ll be entering the entrepreneur game with an advantage.

3. Start slowly. You don’t have to dive all the way in right off the bat. In fact, many businesses started as side hustles.  This is totally fine – and a smart way to go about it.  When you start small, you can see if working in your own business is the right fit for you.  Best part?  You also can grow it incrementally while not losing the security of your day job.  When your side business begins to thrive and you find yourself with enough clients and cash coming in the door, you can make a graceful exit.

Julie Parker

Life Coach Trainer

1. Be prepared to work harder than you’ve ever worked before but also experience more joy, freedom and personal growth than you’ve ever experienced as well.  If an entrepreneurial spirit is burning brightly in you the work will be worth it – and then some.

2. Be your authentic self in everything you do. No matter what type of business you may choose to establish, most people will engage with you based on who you are, what you stand for and your presence as a human being.  And the key to attracting the right people (who are great paying clients and customers, loyal, will come back time and again and speak about you in glowing terms to others) is to always be your genuine self and build relationships where you get to shine as the real you.

3. Surround yourself with amazing people who believe in and support you. Hopefully this will be your family and friends, but it takes a special mindset and understanding to ‘get’ another business owner and the wild and crazy ride it is as an entrepreneur.  Find circles of like minded people, go to events that interest you, find Facebook groups where ‘your people’ are and do courses (both online and in person) where you’re going to connect with people who can lift you up – and you them.  Those relationships will be your savior and your champion at times when you need them most.

april bowles-olin

Business Strategist

1. Don’t worry about how many other people are already doing what you want to do. Lots of creative entrepreneurs that I work with worry that there are already lots of people: designing jewelry, selling handmade ceramics, creating knitting patterns, etc. Keep your eyes on your own paper, and you’ll create something only YOU could create. If I had let the fact that there are lots of other business consultants out there stop me from building my business, I wouldn’t have created my dream business. I would’ve stayed at my day job feeling miserable, wondering what could have been. Even though there are lots of other business consultants, they don’t do things the exact way that I do them. People come to work with me, because they want to work with ME. People will come to you for YOU.

2. Ask yourself if you’re willing to embarrass yourself for your business. This might sound a little weird, but I’ve worked with so many entrepreneurs who won’t take necessary steps because they’re worried about how it’ll look. They won’t pitch an interview because they’re worried they might say something stupid (and embarrass themselves). They won’t tell their friends and family about their business, because they’re worried that they’ll fail and have to go back to their horrible day job (and be embarrassed to tell their friends and families). They won’t inject their personalities into their sales copy and blog posts because they’re worried friends from high school or past coworkers might stumble upon it (and they’d be embarrassed for them to read it).

If you’re not willing to ’embarrass yourself’ you won’t take risks and succeeding in business has a lot to do with taking risks. Do you love this business idea enough to jump in regardless of how it might look to others?

3. Start before you’re ready. When you’re thinking about starting a business, sometimes you put it off until everything is “perfect.” You’re waiting until you can hire a web designer to build you the perfect website or until you take that marketing course that’ll teach you everything you need to know to succeed or until you write a 50-page business plan. The problem with this strategy is that you’re probably going to be waiting forever or at least months or even years before you start. And, the best way to learn how to do these things is to just do them. You’ll learn so much more if you jump in and start the process. I know it’s scary, but if you really want it, start now.

Erin Loechner

Author, Blogger, and Stylist

1. Consider the cost. Every tailor knows the beauty of the edit – a snip here, a cut here. Starting a business is the same. It’s far less about beginning anew and more about releasing the old – whether it’s the comfortable, steady paycheck or the free time on evenings and weekends.

2. Determine the worth. After considering the tradeoffs (freedom vs responsibility, trajectory vs ambiguity), decide if its worth it to you. A great gauge to consider is this: Would I do this work for free? Do I love it enough to offer myself to it daily, weekly, annually, without payment or praise? If the answer is yes, you’re ready. (If the answer is no, you’re still ready. You’re always ready because you’re never ready, you know?)

3. Say yes. Give it a shot and solve problems creatively. Don’t have the capital to invest? Start saving your pennies. DIY what you can, barter what you can, think wisdom over popular opinion. Decide what you need, offer what you have, and enjoy the ride. It’s a wild one.

Sally Hope

Life Coach and Leader of the Wildheart Revolution

1. Ask yourself these three questions before you start:

  • Are you willing to work hard for little money for 1-3 years?
  • Are you willing to have uncertainty where your paycheck is coming from?
  • Are you willing to be solely responsible for your income?

If the answer is YES! Then go for it! If the answer  is NO, then go back to the drawing board.

2. Know WHY you are doing your business. Have a cause that is stronger than flexibility and freedom and a lifestyle that you want because it might take a little longer than you want to get the lifestyle, so you have to love your business enough in order to continue when it’s hard.

3. Have fun! Seriously. Choose a business that delights you and inspires you. I hear so many business owners talking about a business they “should” do because it “makes sense” but if you don’t love it, you probably won’t be able to sustain it.

Kate Swoboda

Life Coach

1. Yes, do it! All the reasons to “stay safe” kept me in a salaried job for a lot longer than I would have liked. Someone once told Oprah that the best bet was to bet on herself. Bet on yourself—not the soul-sucking employer.

2. There’s no pressure to do it all, at once. You can absolutely build a business organically, slowly (and sanely) replacing salaried income with your self-employed income.

3. Expect to market yourself consistently, over time, and to continually learn about marketing. I once heard someone say, “You’ve got to build a runway.” I loved that metaphor for taking flight with a business.

Rachel W Cole

Life Coach & Teacher

1. Can you run the marathon? Starting a business is not a sprint. Overnight success is a myth (sold by people making $ off of hopeful but clueless newbies). Ask yourself if you have inner resolve and outer resources to build something sustainable that might not turn a profit right away.

2. Do your own bookkeeping for the first year so you know how to do it and what’s going on, then hire it out if it you don’t like to spend your time that way. From the beginning though, have a great CPA to assist you with taxes and write-offs and keep your business money separate from your personal always. Have a business credit card, business bank account, etc. First rule of business finance: though shall not co-mingle.

3. Trust your gut. There is a lot information out there about the right way to get clients, write a blog/newsletter/tweet, design a website, structure your services, and on and on. In the end there are many ‘right ways’ and what matters most is if it feels right in your gut.

Jen Carrington

Content Coach + Creative Mentor

1. Start thinking like a business owner. Instead of seeing problems, see solutions. Be okay with thinking about the bigger picture and the nitty gritty details at exactly the same time. Be up for the challenge and pay attention to all the lessons that will come your way.

2. Know your bigger vision. Even if your bigger vision is just “I want a better life for myself where I have an impact in the world,” have something guiding you more than just “I just want to quit my job and run my own business.”

3. Don’t let the details stop you from making things happen. The biggest thing that will hold you back is you. Don’t hold too tightly to your desired outcomes – you probably (almost certainly) don’t even know what is possible yet. Work hard, make smart decisions, and keep on moving forward. Don’t sweat it too much over the things that won’t define your success in the long run.

Jenny Blake

Author of Pivot: The Only Move That Matters is Your Next One

1. Trust your own resourcefulness. You won’t have all the answers up front, no one does. The big secret: we are all making it up as we go along! Something that worked last year won’t necessarily work this year, nor will what worked for someone else necessarily work (or be enjoyable) for you. Worry less about what others are doing, and focus on what gets you in the zone.

2. Run small experiments instead of betting big on blind leaps of faith. Business ideas are like race horses at the Kentucky Derby – run small, low-risk experiments until one or two emerge as the clear winners to double down on.

3. Don’t take failure personally. The best part about running a business is feedback: it is a true meritocracy in that way. If something you try doesn’t catch with your audience, it’s not a referendum on you as a person. Instead, see it as an indicator of skills you can brush up on (like copywriting) or ways you can engage with your community to better understand how to be most helpful. Not sure what to make next? Ask! Run a short survey with Google Forms that asks what their biggest challenge is at the moment, and what they would love to see from you next.

Shelly Waldman

Business Strategist

1. It takes time to build a business. Most businesses can’t take the ‘build it and they will come’ approach. There is a consistent hustle and learning that takes place. So assessing your skills, time availability that you can put into building the business foundation and customer tribe, and desire to create a business that can supplement your income, is a good place to start.

2. Knowing your lifestyle needs. What does it take to live the life you are comfortable living? Look at what it takes to live your life today. Look at this from a sense of time invested to do the things that you like to do (i.e. go on vacation, read a book for fun, train for a triathlon) and the money it takes to afford your lifestyle (i.e. dining out, entertainment, retirement, childcare, kids activities, clothing, food, rent, etc).
Once you have this insight you can begin to do see how one might structure their business both in terms of pricing and in terms of business growth. Keep in mind building a business is different for everyone. Your journey might start with a small side thing to test the waters (remember you testing out both the product/service you want to sell as well as seeing if being an entrepreneur is right for you) vs. diving in head first (however, some people work best under a sink or swim environment).

3. Find a supportive community. Being an entrepreneur is hard. Let me say that again, being an entrepreneur is hard work. You are putting something out to the world, and that can be a vulnerable thing. It’s best to find a community of supportive people who can bring you up when you feel low, can support you, give you feedback, offer advice, share knowledge and be a community you can in turn be supportive to. There’s many of these communities both in person (like a BNI group, chamber, Rising Tide meetings) or online groups (The Lab by Tara Gentile, Female Entrepreneur Association, Caitlin Bacher’s Facebook group For Love and Money).

Bonus tip – One more thing to assess is your current priorities. These priorities may change in a week, a month, heck might be tomorrow. Take the following list and put them into a what is the most important at this point in time: flexibility, money, industry leader, community respect, extra time. Knowing this list of priorities will help you lay a path forward.

Nathalie Lussier

Entrepreneur, software engineer, and international keynote speaker

1. Do a gut check first!  If there’s an idea that’s really standing out to you, take time to discern why you feel drawn to it. A lot of times we feel compelled to go after something just because it looks like a simple project or because it will bring us a lot of money…but that’s totally not the way to approach starting your own business.

2. Take a look into the current marketplace for your idea.  If there’s no competition, there’s a good chance that it isn’t a good market.  But if you notice a lot of similar concepts that are slightly different from your idea, it may be a sign that you can stand out in a thriving market.

3. Make sure that whatever you do hones in on your uniqueness. This uniqueness lies at the merging point of your talents, aspirations, and passions. If you see that your sweet spot can address the needs of your market and that you can deliver on point for years to come, you can be pretty confident that you’ve got a winner business. Although your business itself might alter as time goes by, the important thing to be sure of is that the foundation you lay is based on rock solid principles.

Lisa Congdon

Artist, Entrepreneur, and Author of Art Inc, The Essential Guide for Building Your Career as an Artist

1. Ask yourself: Do I have a healthy relationship with money? Am I in a financially responsible place? Start a business only when you have savings and little or no consumer debt (unless you plan to work a job and have a business on the side). Have enough in the bank to support your life and business needs for at least a few months as you launch and grow.

2.  Ask yourself: Can I visualize and easily describe what success would look like for me? Dream big about where you’d like to be in 3-5 years. Be as concrete as possible about where you’d like to see your business go. Write those dreams down. Then, create a practical plan with smaller goals that will help you reach your big dreams. Don’t know what success would look like or what it takes to reach your goals? Get support from people who can help you get there before diving in.

3.  Ask yourself: What purpose or need will my business serve? What will I offer that will lend meaning or serve a need — not only in my own life — but in the lives of other people? Owning a successful business requires balancing your own creativity and passions with a deliberate plan for a product or service that satisfies a demand in your niche or community. Be clear about what you’ll offer (and why it’s important) before you begin!

Brandi Bernoskie

Owner + Chief Alchemist at Alchemy+Aim

1. Embrace imperfection. Everything is an experiment. Failure is just research and development. Be willing to let imperfection go and treat whatever you create as version 1.0. The next round will always be better than the first. But you need to start somewhere. Don’t wait for perfection to begin.

2. It’s not an arrival; it’s an evolution. You’ll never have everything figured out, and that’s okay. There are always new questions to ask, new situations that will challenge you. Stay curious about yourself and your business. Embracing the continual becoming of your business — and your own continual becoming.

3. Every day, ask how you can serve. When you’re in the trenches of your business, it’s easy to forget your why — why you started it, why you’re still doing it, why this things at all. Take time to connect to it every day and ask yourself how you can help others, those you love in your life, and yourself with what you do. It brings light into the darkest days (and dark days are totally ok).

Sarah Morgan

Badass blog + business strategist at

1. Consider how much of a self-starter you are. One you leave the confines of a corporate job and no longer have someone telling you what you need to accomplish, it will be up to you to prioritize and get to work. It is much easier when you love what you do (I left a corporate job I was not enjoying at all) but you still need to be able to light the fire under your own ass every single day.

2. Also consider how organized you are. Is your inbox loaded with hundreds of opened and unanswered/filed messages? Is your social media schedule haphazard? Creating processes and methods for organizing your work helps to skip over a lot of stress. When everything has a place and a time in your day/week/month you’ll accomplish a lot more in less time. I love and plus white board calendars on my wall to keep everything straight.

3. Lastly, be SUPER specific about what you do and who you do it for. The people that have the most success provide a specific service to a specific group of people. You can be a life coach or you can be a life coach who specializes in helping stay-at-home moms get back into the corporate world. You can be an interior designer or you can be an interior designer helping 30-somethings make their small spaces stylish. This way you’re more likely to be THE small space designer than one designer in a sea of thousands.

Sas Petherick

Coach for Women and Mentor for Coaches

1. Self-doubt is along for the ride. The findings of my Masters research into self-employment and self-doubt indicates that self-doubt is likely to be with you throughout your entrepreneurial life. So there’s that. It can really help to shift your focus from your own worry and confusion, towards the clients you want to serve and the problems you help them solve.

2. Notice the difference between a knowledge gap and resistance. A knowledge gap is a technical challenge that can be sorted out with some training. On-going resistance (to promoting, selling or being visible – for example) indicates a deeper challenge that usually requires a change in your beliefs; in how you see yourself or how you approach your work. And no one can do this for you.

3. It will probably all fall into place (eventually). Learning how to run a business has been the single most frustrating, maddening, take-me-to-the-edge, brilliant, thrilling and most rewarding relationship of my life. It takes time. There are no ‘advanced marketing strategies’. Get clear about who you serve and how you help them. Show up. Keep going. You’ve SO got this!

Jen Hansard

Co-founder of Simple Green Smoothies

1. Measure your enthusiasm. If a biz idea keeps you up at night, you think about it at random moments in the day, you can’t stop telling your friends about it, and you’re always excited about it… it’s definitely worth exploring taking steps forward with. Sure there are biz ideas that can succeed that don’t get you excited, but life’s too short to start a biz that doesn’t excite you!

2. Own your strengths. Take the StrengthsFinder test, learn what your strengths are, and figure out where you are naturally going to have to work harder in your business to succeed solo (or where it would be most beneficial for you to outsource help). This will help you visualize yourself in the business and recognize where you are going to thrive and where you may struggle. It’s important to be realistic with who you are, because not everyone is meant to start their own business.

3. Get clear on your WHY. Spend a lot of time figuring this out because it will help you decide if starting a business is truly what you need to be doing right now. I use my WHY as a compass in my business and personal life every single day.

Breanne Dyck

Founder, MNIB Consulting

Starting a business can be richly rewarding … or terribly frustrating (and often both in the same day!)  Whether it’s the right choice for you, though, depends on your mindset and what you’re really looking for. Here are three questions to consider before you take the leap.

1. Do you want to run a business, or do you just love the dream? I know a lady who has been talking about starting a business for years. She’s got ideas for days, but in all the time I’ve known her, she’s never taken one actionable step toward making it happen. In the end, what she came to realize is that she loves the dream of what running a business could mean for her life, but she wouldn’t actually ever want to do it. And that’s perfectly okay.

2. When’s the last time you learned something completely new-to-you? When we’re kids, we spend a lot of time learning to do things for the first time: first bike ride, first time printing our name, first . As we grow older, though, we spend less time starting from scratch and more time refining our skills and reaching new levels of mastery. When you start a business, you have to be able to balance both and shift effortlessly between them. Your expertise and experience in serving your customers will have to be balanced with a child’s mind for learning what works and what doesn’t.

3. Are you willing to be wrong? Speaking of learning what works and what doesn’t, when you first start your business, you’re going to be wrong more often than you’ll be right. You’ll think you know your customers, and then find out you’ve missed the mark entirely. You’ll have figured out your products, only to realize that you hate producing them. You’ll get excited about a great new idea but come to discover that no one but you cares. The good news is the more you find out what doesn’t work, the easier it will be to find what does — and the closer you’ll get to your ultimate goals and dreams.

Mara Glatzel

Intuitive life and business coach

1. Know that you will never feel 100% ready if you’re defining “readiness” as the “absence of fear.”  You may always have fear. As you move forward in your business, I can promise that you will be surprised frequently by a nagging feeling of self-doubt each time to move into the next level of your work. So, instead of surveying your readiness, try surveying your desire instead. Ask yourself: Is it worth the risk? Do I want it so badly that I am willing to endure the possibility failing? If the answer is yes, begin before you’re ready.

2. Your life – and business – only works if you do. Meaning, your self-care is crucial, if only to make sure that you are able to bring the best version of yourself to your daily tasks. Self-care is the way that you replenish your reserves. The way that you tend to your body on daily basis. As you are thinking about starting a business, it is a fabulous time to learn (or find someone to teach you) how to: make boundaries that feel really good, find space in your day for taking sweet care of yourself, remember that you deserve rest, and take time out for yourself – even when there are emails to answer.

3. Ultimately, building my business taught me what it really meant to have my own back. Don’t forget that you are the expert to your own experience. No on is going to know you better than… you. You have to be the center of your business plan and your strategy in moving forward. You have to play to your strengths – and create a system that works for you. There is a lot to consider when you are considering starting your own business, but one of the most important things to remember is that you are totally allowed to break all of the rules and do it your own way.

Abby Kerr

The Voice Bureau, Founder

1.  Start a smaller business than you think you want. Bite off less than you can actually chew. Start with just a slice. Scale down the initial vision into something that seems exceptionally manageable to you. The one principle of business ownership is that you never end up with the business you initially start. In other words, businesses morph and evolve over time. There’s almost no way to predict what opportunities you’ll feel like saying yes to down the road, so for now, start small and let things grow naturally and organically. Even the tiniest solo-owned businesses have a way of becoming incredibly complex really quickly. Six months or six years from now, you’ll be glad you started smaller than you initially dreamed of.

2. Embrace your strengths. Know your weaknesses. No business owner is 100% prepared in all the ways they need to be to run a business effectively. You’ll develop new skill sets over time, by trial and error, and through making mistakes. Experience is the best teacher. Self-awareness is a core competency of all successful business owners. Decide early on what tasks or aspects of your business you’re fully confident about owning and rocking (the ones in your sweet spot), and don’t wait any longer than you have to to start delegating the other ones.

3. Don’t compromise on the essence of what you want to build. While I advise aspiring business owners to start small and grow organically, I think it’s critical to hold on to the vibe and the particular flavor of the business you want to start. Every business brand has its own signature moves, its way of relating in the marketplace. Figure out the mood, the tone, the voice of the brand you want to create, and be ferocious (yes, ferocious — even if politely) about safeguarding that texture. It’ll set your business apart.

Jennifer Louden

Best-selling author and teacher

1. You can be motivated by your own suffering or others, but then it has to become about the people who will buy. Entrepreneurs seem to fall into one of two camps. The first goes something like, “I am obsessed with ______ and I want to build a business around that.” The second is more like “I see people struggling with ______ and I must develop a solution – now!” I fall into the first category – I started my business with my first book, The Woman’s Comfort Book, in 1992 because I didn’t have any idea how to take care of myself. My business grew from that book when it became a bestseller. Paul Jarvis is an example of the second. He creates courses for creative professionals, and his last course was how to maximize MailChimp. He created it because he learned how to make the email service do all kinds of things that MailChimp had not documented. He saw a need and filled it before the creators of Mailchimp did. You have a natural orientation. Honor it and remember: either way you have to build a bridge to your “just right” people so they understand what’s in it for them.

2. Going into business for yourself is a spiritual and psychological journey. I don’t care what you are creating and selling. Ignore this aspect of self-employment and you may well find yourself stalled with no idea why. Become too precious about your inner struggles and ditto: struggle and confusion. The best practice is being aware your buttons are going to get pushed almost daily – and by the oddest things – so put together a variety of regular support systems to help you process while staying in action. Mine are a mastermind group of like-minded creatives, honest friendships with other entrepreneurs, therapy from time to time, daily meditation, good self-care.

3. Being self-employed does not mean living in nirvana. I am writing this in my sweatpants, unshowered, and feeling behind because my sister called to discuss moving my mom out of memory care and into her house. When I believed every day of my self-employed creative life should shine with soft rose-colored light while I wore a chic outfit and words flew out of my fingers like angels, I was crabby and disappointed. When I became very grateful I could control my creative destiny, create things that helped creative women thrive, and express what’s important to me, my contentment and productivity soared. Ground yourself in reality vs. the myth of working for yourself.

Anne Samoilov

Business Coach & Creator of Fearless Launching

1. Ask yourself this… Can you be patient, work hard, and realistic? Yes I know…sounds like a boring way to look at the exciting world of starting a business. But – coming in with the right expectations is critical. Understand that success doesn’t happen overnight. There is no overnight success. Even the people who seem to have it all pulled together or seem to come out of nowhere have all likely been working at their businesses for months or years. This is probably the biggest challenge for people who want to start a business — it’s exciting in those initial days when you’re getting everything “set up”, but your business is made in the way you spend your days after that!

2. Be social. Start and keep talking to people. If there’s one thing people don’t do enough of (probably including me!) it’s talking to your ideal customers, talking to people you meet in Facebook groups, talking to people who leave comments on your LinkedIn profile. If you want to know what to launch, who to launch it too, and perhaps a promotional partner who wants to help you spread the word about your business. I know that if I could hit the “do over” button, I wouldn’t change much but I’d definitely put myself out there more, ask more questions to help me make the leap to starting my own business.

3. Keep your day job while you figure it out. I know there’s a lot of info online about quitting your day job, replacing your income, making it big with the freedom lifestyle. But do all this exploration, figuring out if you want to start a business, actually starting it, taking those baby steps by staying at your job until it literally stops you from growing. I did this while I was building Fearless Launching. I worked full time running another person’s company while launching 2x a year my own program. I only left the job when I was able to say that the day job was possibly hindering my own growth. But also, I was never stressed about launches because I knew that I wasn’t “starving” or “needing to pay my bills”. You approach things so differently when you’ve got consistent income!

Kelsey Baldwin

Owner + designer at Paper + Oats

1. Be different. Look at what everyone else is doing, and figure out how you can do things differently. Find ways to stand out and not blend in.

2. Just start. You’ll never have all the pieces perfectly aligned, so just start where you are with what you have, and do your best to improve as you go.

3. Be adaptable. You will fail at something, that’s inevitable. Don’t be afraid of throwing in the towel on something if it’s not working. Being an entrepreneur is really just a giant game of trial and error.

Kathleen Shannon

Co-host of Being Boss and Creative Director at Braid Creative

1. Don’t create from a place of fear or desperation. Create a business out of your love for what you do.

2. Clarify your positioning and messaging about what you do and for whom. If you are confused in what you offer and for how much so will your potential customer.

3. Be generous with your knowledge – this will help you position yourself as an expert and create meaningful relationships that will support your business in the long run.

Sarah Bray

Digital Strategist

1. Do it on the side first. Money fears can make even the most ideal, perfect-for-you venture feel like a nightmare. As your business grows, look for opportunities to slowly cut back your commitments at work. (It doesn’t take as long as you think. I was able to take my business from side-project to part-time job to full-time job within a year.)

2. Grow in a way that’s true to who you are. As you’re learning about ways other people have been successful, compare each new piece of information with what you know about yourself. Integrate the learning that is relevant to you personally, and discard the rest.

3. Start as you mean to continue. If you don’t want to build a business that takes up all of your time and energy, don’t start by working 14 hour days and being in constant “hustle” mode. You may have a lot of energy and enthusiasm now, but those feelings will ebb and flow. Design your business to feed you the way you want to be fed from the start.

Mayi Carles de Larrinaga

A Tiny Panamanian Artist With A T-Rex Heart

1. Ignore everyone. And by “everybody” I mean the critics who sit outside of the ring. If you have constructive feedback, bring it on. I want it. I’m an artist. I’m hard-wired to find creative solutions to every challenge that comes my way. I love that. But if you’re in cheap seats, not putting yourself on the line, I don’t care about what you have to say. See something you think you can do better? For the love of all things holy, DO IT. Do it + share it with us. Otherwise, shush your pie whole.

2. Done is better than perfect. It’s tempting to hide in our studio, and then, voila, to amaze us all with your PER-FECT project. But of course, that’s hardly ever the case. What works is evolving in public, with your community. Showing up. Thinking out loud. Failing on the way to succeeding. Imperfecting on your way to becoming better than good enough.

3. Trust the mess. You didn’t come here to be perfect. You came here to be gorgeously human. Flawed and FA-BOLOUS!!! Those biz bosses who are capable of owning their quirks and who require no validations from anyone will be the ones we will be talking about for ages and ages to come.

Tiffany Han

Business & Branding Coach

1. Try to discern if you really want a business or if you’re looking for relief from your current job situation. While rewarding, starting your own business takes hard work and dedication and is not for everyone. If you’re hoping your business will be a quick-fix for getting out of a not-so-stellar job, you will be disappointed.

2. Step away from the internet. Luckily for most of us, the internet is a treasure-trove of resources, but when you’re getting started, research becomes a very convenient form of procrastination.

3. Stay curious and be willing to experiment. If you’re thinking of starting a business, create a product and see if someone will trade you money for it! Get curious about what’s possible and let go of expectations, cause I can promise things never go as planned!

Esmé Weijun Wang

Writer. Advocate for creatives building excellence, resilience, and legacy

1. Are you–and I hate to use this corny phrase, but I can’t think of a better one–a “self-starter”? A lot of entrepreneurship entails motivating yourself to take on the many components of running your own dog-and-pony show.

2. Are you willing to take on what might be a steep learning curve in order to pursue a fulfilling avenue of self-employment? A more fun way of putting this might be: are you curious? If you’re excited about learning about marketing, product creation, content creation, and so forth–if you’re curious about business and willing to pursue a self-styled education in such, you’ll be much happier and much more likely to succeed.

3. And, finally, should you say yes: do you have a financial cushion for yourself, or an exit strategy for yourself from your current work situation that will keep you clothed and fed while you start a business? Practical matters might not be the most exciting thing to think about, but quitting the 9-to-5 immediately and leaping into self-employment can be dangerous without a net.

Tanya Geisler

Leadership Coach and Creator of Impostor Complex 101

1. You love the work you’re about to do, which is fabulous! That said, you’ll spend more time working ON your business than working IN your business, but its growth will require that.

2. Don’t believe lie number 7 of the Impostor Complex that tells you “you’re not ready yet.”  The truth of the matter is, no one was fully ready…for anything. Do it. You’ve done your due diligence. You’re ready enough.

3. You don’t need to go this alone. Gather your people around you. They want to see you succeed. Create a mastermind group, an accountability partnership with another budding entrepreneur, or find a co-working space with like-minded business owners. (Because that’s you…a BUSINESS owner. How wonderful!)

Randi Buckley

Coach, author, and mentor

“Re-examine all that you have been told… dismiss that which insults your soul.”
~Walt Whitman

Most of my business advice falls under Whitman’s umbrella.  But I’ll start with the thing that doesn’t:

1. More than getting advice and seeking solutions, find people who believe in you. There will be times when you start to question your move to work for yourself, and it’s awfully nice to hear from folks who remember what you’re all about and capable of doing, when you have forgotten. It’s not just nice, it can be resuscitation; an oxygen mask breathing new life into your dreams.

2. If advice that’s offered doesn’t work for you, let it go. It’s pretty easy to think there must be something wrong or deficient with you when the advice that is widely touted (retweeted and meme’d) doesn’t suit you, or isn’t working. For me, advice is served like a buffet: take things that will nourish and sustain, and things that suit your taste. Leave what you don’t want on your plate.

Different things work for different people, especially different personalities.  Trying to squeeze yourself into someone else’s way, is like stepping into an iron maiden. It’s going to hurt.

Example?  The ubiquitous rally of the online world: “If it’s not a Hell Yes, it’s a Hell No.” That might hit the nail on the head for some folks, and for some situations.  For example if it’s a deeply thoughtful and complex question you are dealing with, a simple “Hell Anything” might be hell, and way too simplified.

Discern what advice you want and whether or not it suits you.

3. Be honest… is there really a net? You might jump… and a net might appear. But I’d rather make sure there’s a net. I get this might be the buzz kill of the list, but it really hurts to hit the ground without something in place to catch you, or even give you the peace of mind that you can jump.

You see, I was SO excited about the work I was doing and so sure I would do it well. Feeling like my soul was dying in my last gig, I up and left to start my coaching business. I took the leap, thinking “Now I HAVE to make this work. And “Burn the ships, so you can’t turn back!”

Huge mistake.

While I could work my butt off, having immediate revenue traction was not happening. And things went south, financially, pretty fast, having me feel this was all a huge mistake and being in a very compromised position, and risking my dream. So leap! Just make sure you’ve packed a parachute.

Jennifer Lee

Business Coach

1. Be willing to take risks and be uniquely you. It takes a lot of courage to put your creative work out in the world. You have to be willing to stretch beyond your comfort zone to stand out, reach your right peeps, and share your special gifts. Knowing yourself really well and surrounding yourself with supportive people will help you keep going even when it’s scary.

2. Make friends with your moola. If you are going into business, then let’s face it, you’ll need to understand the numbers. But it’s not as scary as you might think. Once you get into a rhythm of tracking your moola coming in and out and checking in with your moola goals you might actually start geeking out on it because you’ll feel empowered. Make it fun – use colorful stickies to make your “Moola Map” or color code your spreadsheets.

3. Keep in mind that it takes time to grow a business. It’s tempting to look at all the amazing things that other people have launched and expect that you can have that out of the gate. What you probably don’t have visibility to are the years of trial and error and twists and turns that got them to where they are now. Dream big and start small. It’s the little wins that build up over time to create sustainable success.

Michelle Ward

Creative Career Coach

1. One of my clients said that owning a business was the biggest self-development tool available, and I so agree. Whether it succeeds or fails doesn’t really matter when you get to learn so much about yourself along the way.

2. I personally feel it’s the best – and potentially only – way to feel authentically you 24/7. When I worked as an Executive Assistant, I was Work Michelle, and then on my own time I was Wife Michelle, Friend Michelle, etc. Now, I’m just Michelle. I removed my masks on my last day at that job in 2010 and have never had to put it on again.

3. You have to be a self-starter and a detective to make this work. If you don’t trust yourself to not spend your days binge watching Kimmy Schmidt, or you don’t think it’s important to make space along the way to reflect on what’s working and tweak/chuck what’s not, then this business will not be what you want it to be.

Molly Mahar

Founder of Stratejoy

1. Are you ready to sell yourself? Whether you are pitching clients, securing funding, networking, or launching products — starting your own business always means you are selling yourself. It doesn’t have to feel slimey, contrived or pushy, but you do have to sell. The earlier you can get on board with this idea, the easier the process will be.

2. Do you have support from your loved ones? Those closest to us might not always understand our ideas or desire to start a business, but their support is vital. Whether that support comes in understanding (less time to clean the house or need to work evenings for a few months), in emotional centering (loving you no matter how your biz is performing or what newbie mistakes you’re making), or in physical forms (providing childcare, extra financial support, or their own skill set to your biz) — don’t underestimate it’s importance. There’s no way I would have kept going in the early, hard years without my husband!

3. Can you get on board with your own capability? When you’re starting a business, there are a dozen things you’ll have to learn from scratch and a dozen more that will push your comfort zone. The amazing part? You’re totally capable of figuring it all out. You can do the hard things. Capable is a super sexy mindset to embrace when striking out on your own.

Jane Riley

Designer/Art Director

1. Get organized with some systems first! It took me a long time to figure out how to invoice, send contracts and keep everything organized. Figuring that stuff out before I got swamped with work would have been really helpful!

2. Make sure you are doing something you love! There are days (6 years in to running my own business) that I am less than excited about work. But because design is something I truly love I am always able to find some aspect that I am excited about that keeps me going – keeps me learning, growing and challenging myself!

3. Don’t take NO for an answer. In the beginning I got a lot of NOs. Maybe not explicitly – but in some form or another things will fall through or not work out the way you had imagined. Don’t take that as a sign that you need to give up! Keep pushing through!

Susannah Conway

Author, photographer, teacher

You need to know that you’re going to become obsessed with your business. It will become your baby and you’ll pour everything into it — and I believe that’s as it should be. The only part of having a traditional job that I miss is being able to leave work at work when you’re done for the day. I haven’t been “done for the day”in seven years, not since I started working for myself. I live and breathe my work 24/7 and while it was never my intention to start a business, it turns out this is where I was heading all along. Here’s what’s helped me thrive (and stay sane):

1. Figure out what makes you tick. I work hard to make my business fit ME rather than contorting myself to fit what others think a business should look like. Start by figuring out if you’re an introvert or an extrovert — what’s your MBTI? Do you like a strict daily schedule or do you work best with wide blocks of unscheduled time? Do you prefer working at a desk or with your laptop on the sofa? If you’re an extrovert who loved being part of a team, make sure you schedule co-working days into your week. To my fellow introverts: try to get out the house once in a while! Working from home is a dream if you found office life draining, but it’s possible to have too much of a good thing.

2. Ignore what everyone else is doing. You want to keep half an eye on social media and stay connected to your audience, of course, but you’ll paralyse yourself if you spend too much time checking out the competition. Trust me when I say it won’t inspire you, it will dishearten you, especially at the beginning. The antidote is to keep your eyes on your own page, exercise and hone your own voice and consciously blaze your own trail.

3. Value organic steady growth. There’s a lot of hype about overnight six-figure success stories but the truth is, it took me three years to hit six figures and I’m glad. It gave me time to build a strong foundation and really nurture what I do. I grew my tribe organically and with integrity and now my biz goes from strength to strength each year. Steady growth lasts. Steady growth is definitely the new black 😉

Kaneisha Grayson

Founder & Admissions Consultant, The Art of Applying

1. If your friends, family, and strangers consistently ask for your help or advice with something, this is likely a strong clue for what your business should offer. Another way to think about it is, “What am I willing to continue doing—but would rather be doing it and being well paid?

2. You don’t need to quit your day job to start a business. As a person who jumped into entrepreneurship with what I thought was a lot of savings ($10,000), I stressed out a lot about money in the first 12 months of my business. I recommend saving up way more than that before quitting your job. In fact, I recommend saving up 12 months’ worth of basic living expenses in addition to 6 months’ worth of estimated basic operating expenses for your business. I know that sounds like a lot, but your wallet and nerves will thank me. When you aren’t wracked with worry about how you’ll pay the rent, you have more energy for creativity and effective execution.

3. Shake the haters off. When you share your dream of entrepreneurship, there will be some people who bring up every misfortune that could happen and who might make you seriously question your ability to succeed. Understand that any negativity you receive from others about your dreams is always a statement about their own limited thinking. This doesn’t mean you should eschew all constructive criticism; just make sure to take advice from people who have what you want.

Stephanie Pollock

Business & Leadership Coach

1. Do an inventory of your skills, strengths, values and interests. These will be your most useful assets as you build the first iteration of your business. The more aligned it is to you, the greater chance it has to succeed.

2. Focus on the problem, not the solution. It’s easy to focus on the bright, shiny solution you could provide clients or customers, but you’ll gain traction by deeply understanding what problem you’re trying to solve. Not sure what it is? Get out and talk to people. Find 15-20 people that likely have the problem you wish to solve, and have a conversation with them. Let their responses help validate your idea (or not).

3. Check in to be sure you’re ready to be a true business owner. Yes, you may also be a fantastic technician (coach, consultant, designer, therapist, artist), but for a business to truly thrive, it must have someone committed to learning the art of business and leading it forward.

Lauren Hooker

Graphic Designer and Founder of Elle & Company

1. Passion gets you started, strategy keeps you going. For most of us, we start with passion of some sort. We really love design, calligraphy, photography, nutrition, writing, consulting, creating, etc., so we set out to pursue our trade full-time and enjoy the thought of being able to work for ourselves.

And while passion usually gets you started, it isn’t enough to run a successful business. You need a plan.

If you look around at the most successful business owners, they think about things differently. They could (and do) take on business ventures in other fields and usually have a great amount of success, even if their business ventures are completely unrelated, because they have a different mindset. They’re strategic, intentional, and they’re smart about the goals they set.
So instead of focusing all of your time and energy on your trade, concentrate on becoming more business-savvy. Creativity isn’t only applicable to your field; it’s also applicable to how you run your business.

2. Bring in multiple streams of income. Depending on whether you’re a shop owner or a service-based entrepreneur, you can probably relate to the ebbs and flows of business. In order to stabilize your income and lessen the risk of a slow month, consider creating multiple streams of income. Within those different streams, brainstorm ways to create consistency (i.e. subscriptions, new offerings, etc.). Over time, these different income streams will allow you even more opportunities as your business grows.

3. You have to be willing to do the work. Entrepreneurship requires you to wear many hats and keep several plates spinning at once. It isn’t about what you want to do; it’s about what needs to be done. It doesn’t always look like coffee shop workdays and pretty desk photos on Instagram. Many times it takes the shape of answering emails, late nights preparing blog posts, and updating spreadsheets for our accountant. But in order to run a successful business, especially at the outset, you have to be willing to do the work.

Shenee Howard

Brand Strategist

1. Think about your goals. Are you wanting to start a business because you love a thing and want to do it for a living or are you wanting to start a business because you want a specific lifestyle? Knowing the difference is HUGE and will help you figure out the approach you should take when starting.

2. If you think that starting a business will provide you more freedom — it won’t, especially in the beginning. Security is not something that is not SUPER common among the self-employed, even for the most successful people. Know that while having your own business is super rewarding, it’s not easy and it’s not nearly as flexible as you think.

3. Know your personality. How easily do you do things without being told? how often do you take initiative? Do you struggle with needing accountability? Is financial stability super important to you?  You can start a business even if you struggle with these things but it will be a lot harder. Honestly, starting a business as sold as a dream for everyone but some people are just not built for business full-time. Before you put in your two week notice, ask yourself if you are prepared to lose some of the benefits (security, 9-5, insurance) of having a job.

Beth Buelow

PCC, author, “The Introvert Entrepreneur: Amplify Your Strengths and Create Success on Your Own Terms”

1. Understand your motivation. Are you running away from a job, a person, or a situation, thinking that by starting a business those issues will disappear? Or are you moving toward creating a business that’s based on your strengths and values? Admittedly, sometimes it’s a bit of both. And it’s important to notice which emotion is in charge: fear or love. Fear is “I can’t wait to get out of here.” Love is “I can’t wait to get started.”

2. Cultivate a support network. It doesn’t matter whether you’re flying solo or forming a team; other people are necessary for your enterprise to be successful. Consider from the start who you want to be part of your support network. Possibilities include a coach, accountability partner, mastermind group, association membership, or an online community. Make connections with lawyers, financial advisors, and technology experts. There’s likely no HR or IT department down the hall, so create those professional relationships before you need them.

3. Understand your energy and lead with what’s true for you, not what you think other people expect or think entrepreneurship is. Burning the candle at both ends has never been my idea of fun. Nor is eating, sleeping, and breathing my business 24/7. Listen to what your body, heart, and mind need. There’s no one ideal image of what being an entrepreneur looks like. Take vacations and days off. Go to sleep at a reasonable hour. Pace yourself and grow at a rate that feels right to you. Release comparisons to others’ entrepreneurial journey.

Melyssa Griffin

Online Business Strategist

1. Have you ever had a job you LOVED? I don’t mean bits and pieces of different jobs, but a single work-for-someone else kind of job that made you feel alive and happy (and also paid your bills). If the answer is “no,” then it’s possible that your dream job doesn’t exist: you need to create it. Look back on the pieces of different jobs, projects, and organizations that you were a part of and search for commonalities or specific things you enjoyed and excelled at. How can you weave those into a new career that’s all your own?

2. Are you willing to fail over and over again? Entrepreneurship is not for the faint of heart and it is absolutely certain that you’ll have some failures and mistakes tucked under your belt before you ever reach any level of success. That doesn’t mean that you need to be ready to live on the streets or eat Top Ramen every night for dinner, but it does mean that you need to have the confidence and courage to be okay with the struggles you may face. Even when they stink, they’re always teaching you something that will push you in the right direction.

3. Have you decided the EXACT person your business will help? One of the most basic mistakes new business owners make is that they create a business that helps everyone or that isn’t very clear in the services or products it provides. Get laser focused on who you want to help and the specific problem you are assisting them with. Then, create products or services that help them triumph over whatever problem they’re having.

L’Erin Alta

Spiritual strategist for women leaders

1. You already have everything you need to begin. So start…now. Beginning a business doesn’t have to be about gaining endless information, accomplishment or experience before you hang out your shingle. It’s about trusting that you already know enough about something to get started.

Honor your path and share your knowledge, right where you are. Create something for someone a few steps behind you. That thing that you would have loved when you were in their shoes. Charge for it. Get feedback. Tweak it. Make/sell/deliver it even better. Offer it again. Refine it until you hit your stride. Voila! You’ve got a business.

2. Failure is inevitable. Do it anyway. Don’t let your fear of failure (or success) keep you from starting. Don’t get distracted by Shiny Object Syndrome, purchasing endless courses and workshops and knick-knacks and doodads, instead of just putting something out there and asking for the sale. Don’t research your business into oblivion, in hopes of finding the “perfect” strategy or formula or step-by-step process that will get you through entrepreneurship unscathed.

Because, my love, you will fail. Fall flat on your face. Completely miss the mark. Bang your head against a proverbial concrete wall until you are bewildered and bloody and bruised. You will stay up too late, get up too early, and wonder when it’s all going to finally pan out. You will be disappointed and uncertain and second-guess why you ever followed this outlandish dream in the first place. You will be tempted to throw in the towel and entertain the idea of getting a “regular” job. You will wonder if it’s worth it.

And then you’ll remember…it is. Because perfection was never promised. Because you’ve got something important and necessary and vital to share with the world. Because you’ve never run a business before and you’re learning. Because you’d rather figure out how to be a successful entrepreneur than a (barely) satisfied employee. Because there are no money back guarantees in entrepreneurship, (and you wouldn’t want one if there was). Because failure is part of the process and it will never be more powerful than your vision, your gifts, your devotion to success. Because…you’ve got this and you are doing it.

3. There is actually no way to fail, because, everything is intel, helpful, useful. Every excellent experience, every tech snafu, every customer kerfuffle is essential to your growth. It all helps you run your business better.

As we’ve established, failure is inevitable (See #2) so, use it. Use it all.

After a How-earth-did-THIS-just-happen?!?!?!!! “failure” ask yourself, ‘What can I learn from this experience? How can I apply it to my business? What worked? What didn’t? How do I want to do this differently next time?’ And then do it.

Nothing is wasted. Instead of taking your past “failures” personally and letting them poison your present, invite them be your teachers. The moment you give yourself permission to be human, to stop beating yourself up for “failing,” to apply what you’re learning, everything changes. Because it’s all useful and you’ve got this.

Theresa Roth

Co-Creator of SuperLoveTees

1.  Start where you are, use what you have. Everyone has untapped resources at their fingertips. The universe has a powerful way for showing up for us if we are open to it.

2.  It doesn’t have to be perfect to offer your services/products to the world.  When I look back at my initial offerings, I see that my products weren’t perfect. There is a lot to learn in any business.  Just start.

3.  Offer something to the world that you love. Living and breathing if a lot more fun if you love it and believe in it.

4.  Bonus!  Not everyone is going to like you or your everything about products/services. That is okay. The ones that do love it are your tribe. They will support you and love you.

Farideh Ceasar

Launch Strategist & Musician

1. Don’t worry about your business name, just start. You’ll try all sorts of things and eventually the right one will naturally emerge.

2. If you’re not sure what your service business would provide, here’s what helped me: Notice what people already ask you for help with. Make a list. Then ask which of these things would someone pay for?

3. Spend time improving your money mindset. We all inherit a money story that shows up as fear in our business around making money, raising our prices and selling. This money story and your self worth exert a heavy influence on your profitability.

Danielle Spurge

Maker + Craft business consultant

1. If you are making a business from something you currently do for fun or as a hobby, get a few new hobbies you enjoy! As soon as your hobby becomes a job, you’ll need something else to turn to for fun!

2. Don’t be intimidated by the amount of money you’ll have to put into this new venture. Often times the things you’ll find you’re spending money on that feel “weird” are things that will ultimately save you time- as we know, time is money, so these things may feel elusive in value but in the long run it’ll be worth it!

3. You don’t have to do everything right now. Focus on a few projects at a time- life is (hopefully) long- and ideas come and go. When one seems lucrative or perfect timing- focus on that one while the others simmer. You can’t do everything at once but you can do a few things extremely well!

Elise Grice

Branding mentor

1. Start with your personal end goal in mind. What do you want your days to look like? How do you want to spend your time? With whom do you want to spend your time? What lifestyle speaks to you the most? Before you start diving into business ideas and products, you must start with what you (as a human being) actually WANT your day to look like and how you want to fill it. The reason why: Approaching your business with your personal goals in mind will help you decide if entrepreneurship is right for you and if a specific business will improve your chances for loving where you end up.

2. Entrepreneurship is all about owning what you do best. This goes beyond the skills you’ve listed on past resumes, to the God-given strengths you were gifted at birth. You must understand these strengths and create your business around supporting + celebrating them. The best part: When you focus on what you do best (and outsource everything else), your “job” will become all about working ON your business and less about working IN your business.

3. If you want to thrive within the world of entrepreneurship, you’ll need people. And, more specifically, you’ll need people pouring into you (mentors), people doing life alongside you (colleagues), and people you can pour yourself into (customers). Unlike a 9-5 job where you can often leave your work at work, starting a business will change your entire life. And you’ll need people alongside you who get it and get you. So if you’re thinking about starting a business, don’t forget about the people who will help you get there.

Catherine Just

Photographer, Artist, Mentor

1. It doesn’t all have to be in place for you to begin. A dream is enough. This is a living breathing thing. You get to create it as you go along. You get to change your mind as you learn about yourself. You can treat it as one big art project in process. The website, the copy, the offerings, the structure… Step away from it all needing to be perfect before you start and Jump In! Allow the business to evolve along with you.

2. Keep your eyes on your own paper. We can easily get caught up in comparing what we see others doing with what we are doing and we can use this against ourselves and think we are falling short, not as good, will never be over there like they are… etc. It’s GREAT to have people out there that you admire and learn from. Just make sure you check yourself if you find yourself judging yourself because of where they are at in their business. When and if that happens, have support to check in with. When you’re comparing your insides to other people’s outsides you run the risk of no longer being inside the solution or inside the creative process for your own business. This is wasting your precious time and sucking life force or energy from you rather than fueling you. Remember that there is enough for everyone. There is no competition. The RIGHT people will be attracted to you. You really don’t want the ones who are wanting you to charge less or do something that doesn’t feel right. Let them go to another in your field. Trust that this is opening up room for the right people to find you. When you switch from comparing to trusting…everything shifts.

3. Continue to learn and connect… Authentically. I cannot say enough about getting out of isolation and into the community out there of other entrepreneurs who are actively seeking to better themselves and their businesses. I took business courses to help me figure out how to be more visible in a way that was true to my own values and not some cookie cutter method. Within those courses I found my unexpected tribe. People I would have never met otherwise (like Laura Simms and many of the people inside this incredible list of entrepreneurs). We not only learned from the people who could help us in an authentic way…we learned alongside each other, supported each other, sent potential clients to each other, lifted each other up through the years and expanded our own understanding of what’s possible from watching each other try out new things and put on different “hats.” Find your tribe, continue to learn, support each other and the collective energy of the whole will be so much more energizing than trying to push and shove your way alone.

Kyla Roma

Business & Marketing Strategist

1. The most important thing isn’t to be correctly prepared or to have a perfect idea, the most important thing is to start. If you’re reading this and wondering if you should start a business, the answer is probably: yes, you should. You’re curious, savvy, and frankly your hair looks great today. Alright, you caught me. I guessed about your hair, but I’ve been having conversations with thoughtful, considerate people considering this question since 2009, and I’ve seen some common themes in that time. (And a strong hair game is just a tip of that iceberg.)

I suspect that if you’re reading this, you’re a little more than curious. You’ve weighed the pros and cons. You’ve been reading up on starting a business, and you want to do it the right way.
I vividly remember when I was in that place. I was hungry for information. I felt a little silly telling people about what I was dreaming but wanted to input so badly. What I wish I knew then, was that you don’t have to see the whole picture, or to have a perfect idea.

Here’s why: Getting started is crucial because as you learn, you change. You solve problems, and you find new ones. You meet new people and uncover new opportunities. You start seeing the world in a new light. You refine your ideas, hone your skills, and that makes you even more equipped to what you want to do.

The most prepared version of Current You has enthusiasm and technique, but Future You has experience, style, and presence. She will add depth and nuance to your solutions in an effortless way. You just need the patience and boots on the ground experience to become her.

Start with whatever imperfect idea you have right now, and get started with what’s most essential. One product, one service, one-page website, one conversation at a time.

2. You don’t need a tidy hero story or to ‘leap and learn to fly on the way down’ to be a business owner. There’s a lot of inspirational stories and quotes out there about getting started, and a particular genre focuses on the idea of giving yourself no way out but to make your idea work. The logic is to leap and learn to fly on the way down. The dramatic story practically writes itself, so it makes sense that these ideas stick around.

The problem is that these stories are often told by people who have a lot of privilege, and therefore opportunity, at their fingertips. There is the assumption that if all else fails you stand up, dust yourself off and get re-hired somewhere as a mid-level manager. But the deck is stacked against some people more than others. For women, single parents, LGBT folks, people of colour, people with disabilities, chronic health issues or mental health issues, the idea of burning the boats is hilarious. It assumes you have boats in the first place!

I started working for myself because I wanted to leave the corporate world – but as someone who has well treated but severe generalized anxiety disorder and depression, being able to work in a way that works best for me has been incredibly empowering.

While you will see tidy hero stories that make a good headline, know that there are hundreds upon hundreds of subtle, quiet stories about people who are just like you. And they’re winning. They work full-time jobs, and at their passion after work and on the weekends. They write blog posts on their smartphones at the playground and work on their business in five-minute bites when their bodies and life allow it. They grow their income, raise their rates and move to part-time work when their work starts to support them. They invest in education and membership to deepen the resources at their disposal. They have bad ideas too, and their email goes unanswered for too long.

Most importantly, they don’t work alone. They join online communities, go to Twitter chats, share the work of people they enjoy and ask their new friends to introduce them to people they could help.

3. Your potential customers are waiting for you to listen. When you have an entrepreneurial fire in your heart, it’s tempting to think that to be successful you need to be the source of all the answers to your potential customer’s problems. What a responsibility! With such high stakes, it’s no wonder that so many thoughtful people get stuck in research mode. How can you, or your company, ever be ready to take on this kind of challenge?

Thankfully, there’s a more humane, actionable way forward. Before you rush into solving problems for other people with your product or service, go get to know your potential customers and ask: “What is your greatest challenge?” with your niche. Ask 10, 50 or 100 people what their greatest challenge with their branding if you’re a designer, or with their online presence if you’re a web guru. Ask open-ended questions, tell them it’s not a sales call, and that you’re gathering information, and get ready to learn.

There are many great ideal customer exercises online, but real people have one advantage: they can surprise you. Real people show you how they think about their problem, their passions and how they value your work. They’ll make your ideas better, and you’ll have the benefit of knowing what your potential customers want to purchase.

Laura Simms

Career coach & Creator of Your Career Homecoming

1. Experiment before you leap. Before you rearrange your life to pursue this new thing, run some small, low risk experiments with it first. Do some small projects for yourself or your friends to get a taste of how this might work as a business, not just a daydream.

2. Talk with people who are doing what you want to do. Learn about what having the kind of business you envision is really like, not just what it looks like on the internet.

3. Know why you want it. Every business encounters hard times and setbacks. To survive these, it helps to remember the larger purpose of what you’re trying to achieve through your business. Think of what the business can do for you and your life, and what you want to it do for your customers and clients.

A hearty THANK YOU to all of the entrepreneurs who weighed in and shared their advice on things to consider as you decide if you should start a business.

If this post was helpful to you, please share it!

Laura Simms is an expert in meaningful work who challenges conventional wisdom by asking people to ditch their passions and start with purpose.

If you have too many passions, zero passions, or can't seem to combine your passions, try her purpose-first approach to find a career you love.  


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