Is Entrepreneurship All It's Cracked Up to Be? It All Depends on How You Approach It

This piece was written with my co-founder and co-author, Amy Abrams.

Two weeks ago in the Sunday New York Times a piece called, "Maybe It's Time for Plan C" revealed the unexpected disenchantment of several new entrepreneurs. They lamented how the experience fell short of their initial expectations -- they worked longer hours, made less money, and felt more isolated.

Surprisingly, many found the job of business owner to be more stressful and less satisfying than the corporate positions they had so eagerly fled. The author of the piece, Alex Williams, keenly observed that if starting their own business was Plan B, then perhaps it was time for a Plan C.

You don't have to be a business expert to know that something has to change for these folks if their effort is going to be worth the trouble. Working 17 hours a day for less than minimum wage doesn't sound like anyone's idea of a good gig, much less a dream job. But the topic begs a bigger question. Given all the hype, "is entrepreneurship all it's cracked up to be?" The answer is yes -- but only if you build a business that meets your needs.

As consultants, we have worked with thousands of entrepreneurs, and are all too familiar with stories of disenchantment. Surprised that entrepreneurship isn't delivering the instant elixir of happiness and freedom they had hoped, new entrepreneurs quickly realize it's astonishingly easy to create a business that is unsatisfying. And from our perspective, it's astonishingly common.

The problem is that instead of figuring out what's important to them and deliberately building their businesses to suit their needs, most new entrepreneurs prioritize ill-fitting conventional wisdom (it's okay to work all the time), things they are "supposed" to do (never say no), and yield to the business' own momentum (I'm too busy to hire help). More often than not, this behavior results in being overworked, underpaid, and employed in a job that doesn't leverage your talents. Not exactly the beacon of fulfillment that people are looking for.

No one said instant satisfaction was the prize for starting a business. Like all good things, it takes a lot of time, some hard knocks, and healthy dose of self-awareness. But the good news is the opportunity for meaningful and satisfying work on your own terms is available for everyone who decides to go out on their own. Of course, it can take a couple of years to figure out how to reap the benefits of being an entrepreneur, but consider those years part of your business investment.

However, the upside to doing it right is huge, and most satisfied entrepreneurs claim they can't imagine doing anything else with their lives. And while the specific solutions they employ always differ there are four things that all successful entrepreneurs share: a clear focus on sustainability, satisfaction, success, and a sense of when enough is enough.


Running a business is a marathon, not a sprint, and it can take a while before you see the financial fruits of your labor. That's why it's imperative to maintain your stamina. This is especially true for entrepreneurs who plan to run their businesses for a long time. Sure, you can work around the clock and sacrifice everything else in your life for the sake of your business, but is that sustainable? Bolstering your endurance requires you to adopt a "work smart" mentality and commit to valuing yourself as much as the business. However, common best practices also help, such as learning to set boundaries, delegate work, keep a clear focus on goals, and employ small steps towards progress.


Happiness is a loaded concept that can force you to focus on external factors. ("Will this make me happy?") Not ones to think of any one thing, jobs included, as life's elixir, we focus on satisfaction instead. What's important is that the job you create for yourself is rewarding, meaningful, and leverages skills where you excel. Some entrepreneurs derive satisfaction from thinking about their business as a whole but actually don't enjoy how they spend their time each day. As your own boss, your job description is completely up to you. Consider how you want to be spending your time instead of just automatically plowing through the list of things that need to be done. If you make certain tasks part of your job, they will stay part of your job.


Our culture tends to glorify size and fixate on numbers. This is even true in the small business world where entrepreneurs often tout and compare things such as top-line revenue, the number of employees and locations, and market share. Entrepreneurs often pursue these metrics at the expense of their own satisfaction, and our seemingly radical belief about business growth is that bigger isn't always better. Measuring success depends on the goals you have for your business. We encourage entrepreneurs to generate their own subjective definitions of success, which may include numbers and metrics but shouldn't praise growth for growth's sake. It's remarkable how differently entrepreneurs grow their companies when they aim for their own benchmarks for success instead of others.

Sense of "Enough"

To be sure there are those who question the validity of growing a business primarily for satisfaction instead of size. In our experience, the two aren't mutually exclusive but the most satisfied entrepreneurs we know are also those who have the healthiest relationship with the concept of what is "enough." Once their business is secure and meets their personal financial needs, they utilize their other business and personal goals to drive business direction instead of continuing in growth overdrive. They recognize the cost of needless growth and instead choose to prioritize what is important to them.

So for the entrepreneurs in the article and those like them, we encourage you not to resort to a Plan C just yet. Instead tinker with Plan B to see if it can better meet your needs. Know that you are not alone in your disenchantment; most entrepreneurs have gotten off-track at some time or another. The good news is almost any business that is "not working" for the business owner can be turned around. The most important thing is to not settle for a business that isn't satisfying. You have the prerogative and power to put things on your terms, after all that's what being an entrepreneur is all about. So be honest and creative and get ready to make some changes. Chances are that Plan B is still the answer; you're just still working on it.