photo by Manuel de Tillesse via Flickr

I do think some people are born entrepreneurs. I’ve met them, and am fascinated by them. These are the people who, as kids, were using their allowance to buy stickers in bulk to sell at a premium to friends in the playground, when the rest of us were merely trading “smellies” for “shinies”. (Forgive me if the girly ‘80’s reference leaves you scratching your head.)
Different from the business brain always on the lookout for the money-making opportunity, many of today’s entrepreneurs are simply people who find themselves drawn to customizing their career in a way that can’t be satisfied by any employer. A desire for the freedom to design their own path. Which brings me to my need to clarify what’s really required- and what’s not- when it comes to hanging out a shingle of your own.

To do your own thing…..


  • An understanding of the difference between a “lifestyle business” and a true “start up”. In this world of a-new-app-a-minute, some think that entrepreneurship means being the next Twitter. That’s one way to go. These businesses are true “start ups”, complete with a vision to scale it to the moon and a willingness to put in virtually unlimited effort to do so. A “lifestyle business”, on the other hand, is one in which you of course make money – hopefully a whole bunch of money – but your aim is to hit a healthy target, pay off your mortgage (or buy your boat) and enjoy life. At some point you won’t want to work more for more dollars. Both types of business can be extremely satisfying.
  • A willingness to meet new people. When on your own, no matter what kind of business you’re in, you’ll have to be a people person (or be good at faking it!) Whether your targets are investors, clients or strategic partners, I don’t know any successful entrepreneurs who hide out at their desk. That said, you don’t have to be a bubbly extrovert; it’s more about getting comfortable with your own style of relating to others. If this part makes you nervous, you might benefit from this from these tips for entrepreneurial introverts from Entrepreneur magazine.
  • A healthy target market. Someone’s gotta buy your goods or services. Make sure what you’re offering brings a benefit to a good chunk of people, and that it’s something they can’t – or don’t want to – do themselves.
  • A willingness to ask for help. Be prepared to reach out to your network and industry experts. Starting a business can be invigorating, but it can also be a slog at times. Learning from others can keep you from making those times harder on yourself than they have to be. Hiring a coach can also keep you focused, accountable and positive.
  • Personal support. Emotional backing is so important. Make sure you have one (or many) people who can encourage you and be a listening ear. If you live with a partner and/or have a family, it’s also important to understand what financial implication is tied to your venture and come to agreements about how money will be managed as you ramp up, and where the limits are. Literally, talk real dollars and timelines.
  • Resilience. Do you believe in the mantras “you get out of it what you put into it” and “failure is rich with learning”? If so, you probably have the natural resilience you need. And if you’re running low, check out the initiative, F***Up Nights (FUN): presentations from brave entrepreneurs who share failure stories and the associated learning for which they’re grateful. Or, just Google “failure stories”! You’ve had the right dose of inspiration when you can say to yourself (in the words of my coaching client on the cusp of taking the leap), “the worst that can happen is I’ll earn a badge of courage for trying.”


  • A never-been-done-before idea, invention, or something “disruptive”. The world needs innovation, that’s for sure. But it’s not the only way to think about going out on your own. You can take something that works and make it better (which is, frankly, also innovation), you can jump into a market that has space for another player, or you can piggyback on something awesome that someone else has already started. (Also referred to as the first follower, described amusingly by Derek Sivers in his TED talk, How to start a movement.)
  • A huge appetite for risk. “Go big or go home” is not the only way. You can start something while still at your current job, or launch a service business with very little overhead. Michael Katchen, the 20-something founder of the wildly successful online financial robo-advisor Wealthsimple, started with only an Excel-based investment template for a few people in his personal network. From there, the seeds took root, and proved something worthwhile to put more in to.
  • A desire to work alone. Working alone doesn’t have to be lonely. You’ll be networking, perhaps collaborating on projects, taking courses, etc. You may opt to build a team around you. And if it’s not enough, create more opportunities to surround yourself with people. Recently, two entrepreneurial friends and I took our laptops to the lake, to enjoy a productive and social workday at the cottage. (Shout out to brilliant founders Amy Laski of Felicity PR and Nadia Sapiro of Throughline Strategy!)
  • A 20-page strategy. Sure, you need some sort of plan. And the more money you’re investing, the more detailed it should be. That said, you can get off the ground by identifying a “best case scenario”, what you think that would take, and where to start. Then you go from there. The bulk of the planning can be done once you’ve worked in the business for a few months and you can see how it might really play out. Don’t get stuck in solidifying every detail before you take action.

Got what you need? What’s stopping you?
“The best time to plant a tree was 20 years ago. The second best time is now.”
– Chinese Proverb