The grass is always greener…

You might not realize it when daydreaming at your 9-5 about starting a small business, but there are a few things to miss when you’re gone. To an entrepreneur, it’s blasphemous to suggest that anything good can come from working for The Man; but going solo isn’t always the end-all be-all.

This entrepreneur is not discouraging you from starting your own business. I believe that independence is the only way to go; but it’s important to be smart about it. Instead of burning all bridges and jumping into the water on your own; take advantage of all the things that both working for yourself and someone else has to offer.

My way is to build low-maintenance, residual income-producing businesses that give me freedom over my time. I then take short-term jobs for the education, not the money.

The Rat Race

It’s easy to get stuck on the treadmill of working for money. There always seems to be a new expense to match every pay increase. The end result is continually choosing a job for the money instead of what you can learn from it.

If you can just use some of your spare time or money to create a low-maintenance business, you will eventually empower yourself in the workplace. You see, when you’re workin’ for The Man because of money; he has control over you. There’s pressure to agree with the boss, mind your p’s and q’s, and generally let the man screw you over.

Working for The Man and not needing his money is a whole different story. You’re doing him a favor. You’re not afraid of being fired. Your confidence shines through and tends to get you what you want.

The Rat Race Part Two

If you don’t know what you’re getting into, working for yourself can also be a drag. Starting a business is an easy way to get into mounds of debt. It’s always more expensive, more difficult, and less productive that you think it’s going to be at first. That’s just the nature of entrepreneurship.

Going it alone can be a lonely, humbling experience. I know several entrepreneurs, including myself, who have caught themselves actually missing their old jobs.

What it Takes to Go Big Time

If you’re like me, you want to go big time. You won’t be satisfied working for yourself if it means barely getting by in a teeny tiny small business that consumes all your time. You want to own something that’s world-class, but still gives you time freedom.

Most small businesses are just that: small. Think of the corner store, or the guy with a little website, or the gal with the consulting business. What separates the little guy from a world-class business?


Financial resources, technical resources, contacts, reputation, world-class minds, etc. These assets are built up through the gravity and legacy of an organization, and can’t just be thrown together. Big companies have resources, small businesses do not.

For example, you can’t just go out and start an aerospace company. If you’re starting with nothing you will never be able to assemble the team of experts, government contracts, and enormous financial reserves you would need to compete with Boeing and Airbus.

That being said, it would not be inconceivable (if you started at a young age) to start by building financial freedom with a low-maintenance business. This would allow you to take a new job every two years in every possible department of both Boeing and Airbus.

The foundation you would have created with your low-maintenance business would give you the freedom to only take the most interesting jobs; and the confidence that you would need for promotions.

Twenty or so years of this process and you could have a sound-enough understanding and complete-enough rolodex to solicit the funds to create your own aerospace company.

Extreme, but possible! I don’t have the patience, nor the desire to take on a challenge that big; but if a person could do that, they could do anything.


My desire is to make movies. It’s not aerospace, but the millions of dollars it takes to make a movie puts up quite a barrier to entry.

Fifteen years ago, a guy like Robert Rodriguez could donate his body to science for a few thousand bucks, run around with a camera, and cut together a movie with blood, sweat, and tears; but it’s not as easy today.


    1. it’s a whole lot easier to do if you have no debt and a low-maintenance business to live on in the process,


    2. why not spend a few years volunteering under Rodriguez, Tarantino, or Linklater to learn from the best? No sense reinventing the wheel. Working a low-paid film job will teach you how movies are made and put you in touch with experts who will make your life a lot easier when it’s your turn.

Benefits of Working for The Man

Working for The Man is a tough gig, but don’t let it blind you from the benefits. (When I say “The Man,” I’m using the term loosely to include working for anyone other than yourself.)


As entrepreneurs, we often think that we do everything on our own. Creative people who are talented can be lured into the illusion that they don’t need to learn any more.

In reality, there’s no one who knows it all. Organizations have money to hire experts. There is so much to learn from people who have spent their whole lives refining their skills in an industry. This kind of knowledge can be invaluable.

Proven Processes

You might have a million dollar idea, but there are just certain processes that tend to work better than others in each industry.

Processes are a boring subject for creative people, but vital to success. Spending some time in the industry of your interest can teach you best practices that will make your entrepreneurial life much easier.


No one does it all alone. A great leader knows a little about everything, but finds a group of people who are experts in their field.

Working in your industry puts you in touch with those people. You can’t put a price on the bonds you can make while working in the field. Interviewing candidates for you team is no replacement for working side by side with them.


One of the first things that I missed about old jobs when going solo was being around people. You forget how much friendly relationships add to your life.

Whether it’s saying hi to the receptionist every morning or chit-chatting with a co-worker when you’re supposed to be working; people are the most meaningful aspect of any job.

Your Turn

It takes a little patience and humility to put in your time for someone else before going it on your own. It’s a mistake to make the leap too early, but it’s also a mistake to never take it at all.

Be smart with your strategy and reap the benefits of both working for yourself and The Man by building low-maintenance businesses and taking jobs for the education, not the money.