The Psychology of Being an Entrepreneur

Entrepreneur Frustration
An Irish entrepreneur I know asked me yesterday how I’ve dealt with the ups and downs of starting a company. For all the books, articles and blogs on entrepreneurship, there is surprisingly little discussion on the emotional side of being an entrepreneur. Until I read Brad Feld’s post Something Is F’ed Up In My World Every Day, I’d never really heard another entrepreneur / investor directly talk about their feelings.

But starting a company ranks up there as one of the most irrational acts a person can perform. To create a business you must put at risk many of the things you hold dear: financial security, emotional security, professional security, and any semblance of work-life balance. And while the motivations for doing so vary by person - e.g. money, recognition, professional success - I think most of us do it because of an uncontrollable desire to create something new.

The Challenges

Whether you succeed or fail, building a business is hard. Really hard. Here are a few of the common emotional challenges of starting a company:

Challenge #1: Burnout

It can take long hours to start a company. In my first year starting CloudHealth, I worked 6-7 day weeks averaging 12+ hours each day. I did it because I had to; this is what it took to identify a market, build a product, create a plan, acquire customers, find investors, and perform the hundreds of other things required to create a business. Consistently working long hours almost always leads to burnout. And unfortunately there is no over the counter prescription for recovering from burnout once it hits (and it always hits).

Challenge #2: Fear of Failure

There is no fear for an entrepreneur quite like the fear of failure. I still remember the looks I received on letting friends and family know I’d quit my job to start a company. As much as I knew I was taking a managed risk, there was no easy way to make others understand why the sole income earner of a family of four would quit his job for the hope of starting a company. Even today that fear is never far from me, and I am still occasionally struck by the feeling that I'm one bad decision away from failure.

Challenge #3: Rejection

If you are starting a company, get ready for a lot of rejection. Unlike the rejection you get in the professional world, this rejection can often feel very personal, since you put everything on the line to start your company. In some cases you will find the rejection helps build a better business, and in other cases the rejection comes from pioneering a new idea or product. In either case, it's hard to not take the rejection personally.

Challenge #4: Loneliness

Brad Feld makes a case in Do More Faster that startups with multiple founders have a much greater success rate than startups with single founders. While this didn’t dissuade me from going it alone, this still rings true for me. Teams have a built-in emotional support for handling the ups and downs that come with creating a business. I still remember the days in which I went home at night after being rejected by a prospective customer, investor and/or colleague, questioning why I was even trying to start a business when it was so clear to everyone around me I was going to fail. Regardless of whether you start your business by yourself or with a group, prepare yourself to experience this isolation.

Challenge #5: Emotional Roller Coaster

Building a company is a high intensity roller coaster ride. The highs can be really high and the lows can be really low. No matter how successful your company becomes, you will experience both repeatedly over your journey. While it becomes slightly easier to cope with the lows when you have some demonstrable success, you'll never quite get used to that low feeling that comes with the failures.

Challenge #6: Over Responsibility

With each person you add in your business, you feel a sense of relief that comes with having others helping you build the business. But each new person also brings a nagging sense of responsibility. This feeling can be especially acute for your earliest team members, who took the biggest personal and professional risks to join you. To repay them, you may feel a powerful drive to create success for them professionally and financially. The result is often an ever present sense of responsibility for the livelihood of the people around you.

Challenge #7: Need to Demonstrate Success

In the early days of the company, it seemed everyone wanted to ask me how my business was going. The interest always came from a good place, based on a genuine interest in knowing more. But it also created the odd dynamic in me of feeling the need to constantly provide some external proof of success. Unfortunately there is nothing linear about building a company, and sometimes demonstrable success is a trailing indicator to actual success.

What You Can Do

Here are some of the things I’ve found to help me cope with the emotional challenges of being an entrepreneur:

Tip #1: Advisors

When I first started CloudHealth, I solicited the support of a handful of advisors to help guide me through the early phases of building a company. These advisors included entrepreneurs, CEOs and startup executives. Each had a unique expertise that compensated for one or more gaps in my own, and each had a vested interest in helping me succeed. I would often (and in some cases still do) meet with my advisor every few weeks to share my progress and receive suggestions. In addition to providing business help, advisors can be cathartic for your mental health, helping you recognize you are not alone on your journey.

Tip #2: Reading Tech Histories

I am a voracious reader of tech histories, especially the founding stories of successful companies. I find in these stories ideas, guidance and inspiration. While each successful company has a unique journey, they all share one common storyline: struggle. As much as we like to think Larry and Sergey went from a dinner check from Andy Bechtolsheim to IPO, the reality was that a lot of struggle occurred in between. Getting behind the rags to riches storyline to the real messiness of building successful companies can help keep you mentally grounded.

Tip #3: Embracing Failure

I've experienced dozens of failure in the last three years. My instinct as an entrepreneur is to try to bury them deep inside, never discussing them, and instead just pressing on. But from experience I’ve learned that the willingness to embrace and share failure often frees you of some of the bad feelings associated with them, and can help you move on. Find a few key people with whom you can openly share your failures, both to help you put it in perspective and help you improve your company.

Tip #4: Maximize Focused Mode

The Mayo Clinic Guide to Stress-Free Living describes the two modes of the brain: focused mode, where your mind is fully engaged in a task, and default mode, in which your mind ruminates over past injuries and future threats. The book asserts that the default mode is a powerful adaptation in humans for a time in which we were surrounded by potential threats. Unfortunately in a world in which a saber tooth tiger is not likely to jump out and eat us, allowing our brains to spend too much time in default mode can create stress and have a negative impact on our lives. You should find techniques to help maximize your focused mode each day. For some this will come from exercise, meditation, family time, writing a personal journal, or even just blogging. Whatever your technique is, find it and make it work for you.

Last Words

Being an entrepreneur can be exciting, challenging, and rewarding. But it also an emotional roller coaster that can take a toll on entrepreneurs. Whether you succeed or fail, you'll almost certainly be challenged professionally, personally, financially, and emotionally.

Keep in mind that you are not the first person to ride the roller coaster though. The twists, turns, highs and lows you experience are what every entrepreneur who has ridden the ride before you has also experienced. So when you feel the downs that come with building a business, I hope you can leverage these tips to keep yourself in your seat. So buckle up and embrace the ride: there is nothing like it in the world.


Related posts: My Lean Startup Journey, Reflections: 1 Year Post Funding