Select Page

I recently mentioned to a talented designer that I used to own a marketing agency.  “I wish I owned an agency,” he mused.  I asked him, “What attracts you to owning an agency?”  He said that he enjoyed working in a collaborative environment with other talented creative people.

“Are there other ways to do that,” I asked, “without owning an agency?”

When you love your craft and you’re good at what you do, you may believe that your next step is to start a business for yourself.  You may even receive such encouragement from your friends and family. “You should start a business — you’d be great at that!”

Having been self-employed for more than a decade, I’ve learned many lessons along the way, and I have caught myself countless times saying, “If I knew then what I know now…”  Here are three questions I would have known to ask before I dove in head-first into the world of self-employment.

1. What’s your business personality?

Not all workers are wired in the same way.  In his classic book The E-Myth Revisited (Amazon), Michael Gerber describes three distinct business personalities, technician, manager, and entrepreneur.  Here’s a brief overview of each of the three personalities.

Entrepreneurs are strategic thinkers.  They carry the vision of the organization and develop the systems and processes that allow it to function.

Managers implement systems and processes required for the day-to-day operation of the business.  They excel at consistency and maintenance.

Technicians are the makers.  They enjoy doing the day-to-day work.  Many would-be business owners start here — they love their craft and they’re good at it.

While certain elements of our work and leadership styles are innate, Gerber believes that prospective business owners can develop their abilities.

If you’re not naturally bent toward an entrepreneur type, that doesn’t necessarily mean that you shouldn’t be a founder. It does mean that you’ll need to acknowledge your “baseline” and compensate in some way.  You may seek a program (such as a startup accelerator) to help you grow in this area. Alternatively, you may recruit a co-founder who is strong in business development while you function as a technical co-founder.

Which brings us to our next question.

2. Should I go it alone?

Conventional wisdom says that two-person founding teams tend to have the best outcomes. “Conventional wisdom” is also never universally true. Success stories exist for single-founder companies (e.g. Dropbox, Mint) as well as multiple-founder companies (Youtube, Twitter).

You may not be interested in starting a “startup” per se, but you’ll need to ask the same questions about any business venture.  Should I go it alone?  Or should I start up with a partner or partners?

While there is no correct answer, there are some considerations.

  • What are my goals? Am I trying to build a small lifestyle business (including freelancing), or am I looking to build a high-growth business?  The more aggressive your business aspirations, the more help you’ll need.
  • Do I have the requisite skills to run a business?  I can build a website. I can execute a marketing campaign. But if you put anything legal or financial on my to do list and you’re going to have problems.
  • How can I staff my weaknesses?  You may not necessarily need a partner or co-founder to staff your weaknesses.  You may be able to outsource some functions (such as bookkeeping) or hire full- or part-time help to support you in those areas.

Regardless of the route you take, you shouldn’t fulfill every role in your business. Instead, you should focus on what you enjoy and what you’re good at — and you should outsource the rest.

3. What are my alternatives?

Of pastoral ministry, Spurgeon wrote:

If any student in this room could be content to be a newspaper editor, or a grocer, or a farmer, or a doctor, or a lawyer, or a senator, or a king, in the name of heaven and earth let him go his way; he is not the man in whom dwells the Spirit of God in its fulness, for a man so filled with God would utterly weary of any pursuit by that for which his inmost soul pants.

I believe that the same is true of entrepreneurship.  If you are content to do anything else, do it.  (Coincidentally, this has been the driving force behind my ongoing transition from business to ministry as God has shifted my passion from the workplace to an unquenchable desire to serve his church.)

There was once a time when I would have argued the opposite — that anyone can and should start a business of their own. But after nearly a decade of freelancing and business ownership, I’ve discovered that the responsibilities of owning a business are tremendous.

I would, however, advocate for everyone to at least try to develop a side hustle that serves as a creative outlet and as an independent stream of income.  Even if it’s a seemingly insignificant endeavor, the rewards that accompany starting something of your own are paramount.

Here are some alternatives to full time entrepreneurship. These are also good “next steps” if you believe that full time entrepreneurship may be a good fit for you.

  1. Leverage your day job. Use the opportunity that you have in your current role to hone your craft, and re-purpose your work to begin building a portfolio (which will be a valuable asset for attracting customers if you go freelance or commit to running a business full time.)
  2. Start a side hustle. Look for opportunities to trade your knowledge or services for revenue.  At different times, my wife has earned some side revenue making cloth diapers, designing social media graphics, and other opportunities.
  3. Practice wearing the “entrepreneur” hat. How would you start a business if you only had two hours per week to spend running it?  (Listen to this short episode of The Tim Ferriss Show for more on this idea.)

What is your next step?

In retrospect, I would do it all again if I had the chance. I would be wiser, and I would do things a little differently. But the journey has been incredible and next to encountering Jesus and starting a family with my wife, working for myself has been one of the most transforming experiences of my life.

Now that you’ve processed these questions, what’s your next step?  Remember that you can explore almost anything as a short-term experiment.  Be bold, be daring, and try something new.