Three Reasons I Can’t Go Back to Working for Someone Else

8 min readNov 1, 2016

I’ve always been an entrepreneur at heart. My first businesses involved mowing lawns in the neighborhood and renting our internet access to friends. As a serial entrepreneur, I run a few businesses. Thankfully a bit more successful than helping out Ms. Johnson background~~ and some teenage boys get their BayWatch fix.

However, like most of us, I spent some time working for some else.

I had a good job, a good salary and an even better boss and team to work with. It involved a lot of travel globally and I was given a lot of freedom to manage large projects.

However, it never felt right. I loved my job, my coworkers and the work we did. But not once did I feel like I was doing what I was meant to do. That I was doing my life’s work. That “this” was it.

A lot of people have dreams of being their own boss and running their own business. I was convinced I could do so on my own terms. That jump takes a lot of risk and with it comes a perpetual state of doubt and uncertainty. A lot of times, failure happens. Things don’t go as you planned. Things don’t work out like you intended. No one actually wants to pay you!

Sometimes you think that means its time to go back to the corporate world. That its time to polish up the old CV. Where it feels like time to go back and get regular paycheck. To pack up your things, swallow your pride, tuck your tail between your legs and head on back to the job market.

The following are the 3 reasons I could never go back to that life:

Vacation/Leave Request Forms

Of all the stresses of a “job” the most irrational process to me is the idea of requesting a day off.

What? What world is this?

Despite a recent trend of unlimited vacation days most companies operate on an old school method of “earning” vacation and sick days as the year progresses.

“The BLS reports that workers with one year of experience average ten days of paid vacation. Employees with five years of experience average 14 days of vacation, workers with 10 and 20 years of tenure average 17 and 20 days respectively.”

Oh and let’s not forget, “use it or lose it.” The premise here is that I’m such a good worker and I worked around the clock week after week not taking any days off. And then how do you reward me? By taking away the vacation days I’ve accrued because I didn’t take a day off. Seems counter intuitive no?

To be honest, this is solely a matter of principle for me. I think in the last 4 years I’ve maybe taken a combined 6 or 7 days off. Many a holiday and family trip I’ve spent starting at my phone or laptop or at least day dreaming about the companies I run. I work 12–16 hour days and I don’t take vacations. It’s not something to boast about but I’d rather be at my desk than sleeping in.

What this really is about is principle. The principle that when one wants to take a day off they can’t. They have ask for permission. To go to the doctor, to take a long lunch with an old friend, to play hooky with your partner, to sleep in. To just not feel like coming in.

That lack of freedom is jarring to me.

How many excuses do you have for when you need to get out of work? How many times has your dog died? Or your great aunt Ruby? How many emergency dentist visits have you come up with? Or food poisoning? Jury duty? Your house is flooding?

You can Google “Excuses to get out of work” now and it’ll come back with 63,000,000 million response.

63 Million!

“Work was intended not to give a man a reason to live, but rather to give him a means to live.”

Vacation and leave request forms take away from what work is really about. Purpose.

The thought of going back to a life I need a constant escape from? No thanks man. The thought of a life where I need an encyclopedia of excuses to take some time to myself? Nah fam.

When I finally do decide to take an afternoon or day off it’ll be because I just feel like it. And I’ll be free from doubt and excuses.

Just surviving isn’t even enough for the zombie apocalypse!

Just Surviving Isn’t Enough

As mentioned before, I loved my previous job. We got paid to do good, life saving work in the global health space. We got to change peoples lives from the grass roots level all the way up to national and international policy.

I was good at my job. I consistently performed well year-on-year and had great relationships with my seniors. I filled up many a passport traveling the world. For all purposes, this was a dream job! I mean who will say no to earning US dollars while living overseas?

But I never felt at home.

That industry and others I’ve worked in never felt right. I could do it and do it well, but it never spoke to my core. I felt like I was constantly faking the funk.

Sometimes despite your skills and even perceived happiness your personal growth can feel stifled.

I was lucky I got to do amazing work and work alongside amazing people. However, most in the corporate sector are neither excited by their tasks nor colleagues.

If your day job doesn’t offer personal growth, it may be time to quit.

When I decided to leave my boss offered me another position and even contacted me some time later asking if I’d like to come back.

However, I knew I couldn’t continue wasting their time or mine. My heart was no longer in it. To many what seemed like a great opportunity for growth and success, I saw as claustrophobic.

Now I’m in full control of my fate. I can decide what I want to do each day, when I’ll do it and most importantly, what I don’t want to do. I work and live on my own terms. I might not have the full road map figured out but I have the freedom to make it work.

Entrepreneurship isn’t about earning more money. Trust me. It’s not about living this amazing life, sleeping in, 4 hour lunch meetings and endless wine filled networking events.

It’s rooted in passion. I’d do what I do now for free (for years I have! hehe) While it has its hard moments and the temptation sometimes creeps in, I’d rather struggle on my own terms then live comfortably in a life that doesn’t speak to me.

Be honest to yourself. Are you really happy? Or just surviving?

Yes, it’s cliche but life is too short not to live it on your own terms. Grab it today and do what you want to do.

“I thought you were smart…”

When I finally decided to leave my job I had a long phone call with a very close friend who was also my senior and mentor.

After listening to me spout about my passions and unclear plan about what exactly I was going to do she paused for a long moment…

“I though you were smart,” she sighed.

She was so disappointed. I’ll never forget her voice.

How could someone so intelligent, with proven success, leave a good job to do something so silly as start their own business She was genuinely confused. And upset.

In all honesty, that statement almost broke me.

What if she’s right? This is the stupidest idea I’ve ever thought about. I know nothing about running my own business. This job is a good job. So many more people would love to be in my position. And this is my mentor. I trust her! She’s guided me and helped me grow so much. Now she thinks this is the worst decision I could make? I can’t leave…

And then I snapped out of it.

Worrying about what someone else thought of me almost put a freeze on all my dreams. That statement didn’t let me stumble but instead solidified that I’d rather be broke and unsure than work somewhere that looked at me in that way.

Entrepreneurship isn’t rational. It doesn’t make sense to leave stability and certainty for challenges, financial despair and a long path. It certainly isn’t for everyone or for everyone to understand it.

What do you want your life to be about? What do you want your last days to look like? Regret? Knowing you never tested yourself and pushed boundaries? Like you wasted potential because you were afraid of what other people thought?

I should thank my old friend. She’s directly responsible for keeping me going each day.

“I thought you were smart.”

Those words encourage me every day. Every time I think about giving up, every time I doubt myself, every time I think about turning the other way.

Jump if you’re supposed to jump

Lastly, please internalize that hating your job does not automatically mean you should be an entrepreneur. Just because you hate working for some else doesn’t mean you are meant for this either. Maybe you don’t enjoy the politics. Maybe you don’t like your boss. Maybe you don’t relate to your company’s ethos. There’s a lot of uncertainty that you need to assess before taking this jump.

I’m a lifelong entrepreneur. That’s not going to change.

Each day I get the opportunity to not only do what I love but to help others succeed and grow. Bit by bit things look up and I’m building my legacy (and hopefully my net worth.) Despite the pains and difficulties, there is absolutely nothing I’d rather be doing.

Working for yourself requires a tremendous amount of true grit, self belief, courage and plain old hard work.

If the reasons above speak to you in any form, you owe it yourself to try to live the live you were intended for. The right time? It’s always right now. Go out and get it today.

And stay away from vacation request forms.

Are you an entrepreneur? What’s kept you from going back into the corporate world?