5 Reasons to Take the Leap and Be Your Own CEO



If you’re experiencing fatigue at least five days a week, hypersensitivity to everything office-related, including timecards and long meetings, and nausea at the thought of staying at your current job any longer… then you’re probably suffering from what I call a “corporate allergy.”

Unfortunately, this sort of allergy isn’t relieved so simply as popping a few Claritin. If you’re in this position, don’t worry (I’ve been there, and help clients through similar situations every day). It’s just time to get clear about what to do next.

You’re probably looking at three options: the first is to find a better job. The second is to embark upon a radical career change, like my client who’s taking the leap from pharmacy to fashion design. And the third is to take the leap from corporate life to being your own CEO, a term I use to encompass being a freelancer or consultant, launching a startup designed to grow rapidly, or building a small business around your passion.

If the idea of taking the leap makes your heart beat a little faster, listen up. If you value freedom, adventure, and purposeful work, read on!

When I took the leap in 2010 from a successful career in design to launch a personal growth startup, I had a dozen reasons not to do it, like not being cut out for entrepreneurship or thinking I was too young. And yet I took the leap, and I’m so glad I did.

Being your own CEO isn’t for everyone, and, without knowing you, I can’t say that it’s your best option. But here are my top five reasons why being your own CEO is worth exploring further.

1. You have freedom and control of your career.

Being stuck in an office for 8 or 10 or more hours a day is a bummer. While some enlightened workplaces allow for more flexibility, being your own CEO offers the ultimate freedom.

You have the freedom to dial in your work routines to match your energy level, not the other way around. You also choose how much work to do, balancing your ambitions and financial needs with the rest of your life. More importantly, you also have control over the nature of your work.

2. You can pursue your passion and purpose.

You don’t have to create one more cookie-cutter web startup. (Honestly, please don’t.) You can launch a startup or freelance business that’s based on a personal passion of yours, has a social or environmental mission, or both.

If you’re not going for passion and purpose, you’re missing out on one of the best things about being your own CEO. As Guy Kawasaki said,

“The best reason to start an organization is to make meaning – to create a product or service to make the world a better place.”

My first startup, the Reinvention Circle, was a safe haven for “Reinventors” – people from all walks of life who were forced to reinvent themselves after being hit by the “Tsunami of Life” – divorce or breakup, being laid off, bankruptcy, spiritual crisis, sometimes all of the above.

I worked with a team of coaches from around the world and dedicated 18 months of full-time work to this endeavor. Our donation-based business model filled my heart with a sense of purpose, yet it didn’t fill my bank account. In the end, I burned through my savings and made a paltry $800 when we closed the books.

My current company, Masters of the Leap, was my second chance. This time, I’ve been able to balance my mission (to help extraordinary 20 and 30-somethings have more freedom, adventure, and purpose in their work lives) and make a good living at the same time.

Don’t let anyone tell you it’s impossible to build a business that’s brimming with mission and passion that also brings home the bacon. It just takes some tinkering to get there.

3. It’s an adventure.

The fact that entrepreneurship is risky also makes it exciting and fun. Perhaps for the first time in your life, you’re going all-in. You’re giving up a steady paycheck and putting your livelihood on the line. Without a boss to blame, the responsibility for success and failure is all yours.

If that sounds more terrifying than exciting, take a deep breath. Fear is simply excitement without the oxygen.

Once you’ve accomplished that, you can ask yourself these two questions:

“What’s the worst that could happen?” Look your fears squarely in the eyes. Then come up with a backup plan in case your new venture doesn’t work, whether that means getting another job or living at your parents’ house for a while, which is exactly what I had to do at one point. Luckily, my parents are good people, and their fridge is well-stocked. All-in-all, my backup plan wasn’t that bad. Having a backup plan will put your mind at ease. Hopefully, you’ll never have to use it.

“Will it be worth it even if I fail?” Even though the Reinvention Circle failed on a financial level, the experience was well worth it. I referred to this first startup as my “trial-by-fire MBA.” Those lessons were the foundation for my current success. I wouldn’t trade that learning for anything.

4. You’ll learn a ton.

Do you know that feeling of arriving in a foreign country and being keenly aware of how different everything is? For a few days or weeks, before you start taking everything for granted like you did at home, your senses are sharpened. Every little thing is novel – the language, the way people interact, what street signs look like. You can almost feel your neurons rewiring.

Being a first-time entrepreneur feels a lot like this. You’re wearing many hats and learning new practical skills, like sales, marketing, and operations. More fundamentally, you’re shifting from an employee mindset to an entrepreneurial mindset. It’s like you’ve stepped into a strange new world.

Especially if the learning curve at your current job is tapering off, entrepreneurship can be an appealing option. Just don’t worry about trying to learn it all before taking the leap. If you know half of what you need to know and hire a good coach to support you, you’ll learn the rest as you go.

5. It’s better to do it sooner rather than later.

I tell my clients in their 20s and 30s that it’s better to take the leap while they’re young. Not that it isn’t possible to do it later, but once you have major family and financial obligations, everything gets more complicated.

There’s a saying of unknown origin that you’ll hear around the startup community: “Entrepreneurship is living a few years of your life like most people won’t, so that you can spend the rest of your life like most people can’t.”

There’s a lot of truth in this. Being a first-time entrepreneur is like learning to ride a bike. You’ll get some bumps and scrapes, but once learn to ride the bike, you’ll have that ability for life.

So what should I do?

In the end, it all comes down to personal preference. Some people enjoy a life that’s smooth sailing, and entrepreneurship is not for them. Others enjoy a good challenge, a somewhat wild ride with higher highs and lower lows.

If that’s you, you may be ready to take the leap. Later, you may look back thinking, “What was I so scared about? That was awesome!”

Ready to take the leap?

It Starts with “Yes.”

Peter Rubin works with young professionals who want more freedom, adventure, and purpose in their work lives. He is also a GA instructor in San Francisco.