Let's face it: we're all a bit institutionalized. 

Even if you work at a smaller company ("we're independent!") or work for yourself, we all think about work as though it's a place. And in your workplace—whatever it is—there's probably some semblance of order and authority if things are getting done. 

There's some institution in most anyone with a modern education. Most of us experienced school in roughly the same way: as a structured experience with hierarchies, boundaries, punishments, and rewards.

This isn't necessarily bad; structure can help, and hey, things like school become a shared experience growing up.

Then, once you're out of school, there's a tried-and-true way to stay comfortably in structure for life: get a job, work hard, climb the ladder, spend wisely, and accrue wealth and privileges until your retirement. If you're happy and don't need more freedoms, this might be ideal to some of you.

 

But many of you examine that option and say...

 

 

Maybe you don't want to take a position working for something that you have no passion for, that you simply don't care about (or perhaps actually dislike), just so you'll have a steady cashflow.

Maybe you don't want to work hard in the precise manner most others do. Maybe you need flexibility, or maybe you work best at weird hours, so the usual 9-to-5 hours rub against your grain.

Maybe you don't want to spend a decade or more "paying your dues" and putting up with B.S. while you wait for the next opportunity.  

Maybe you don't like the idea of working 50 "meh" years so you can have 10 years of retirement when you're least able to use them.

Maybe you would rather accrue your wealth and privileges as you earn them, not when someone else decides to give them to you.  

 

 

 

If any of the above applied to you, here's the good news: you CAN make it yourself, and this article will tell you how to start figuring it out. 

 

One: Identify your motivations

Every person has reasons for leaving one job or starting another, but that doesn’t mean all reasons are good. If you can’t say why you want to do it, it may not be a great idea!

Do yourself a favor: rid yourself of the notion that creating your own job also creates wealth, success, or sex appeal. It’s true that people respect you a bit more for making yourself; it’s true that creating your job means doing what you want; it’s true that only the self-employed have a limitless potential income. But if those rewards come at all, they usually come after deprivation.

Starting out requires entrepreneurs to tighten their personal income, cut into their own free time, and do lots of things they don’t want to do. The wrong motivations will crush you when things start feeling heavy. The right motivations, on the other hand, will keep you fighting and passionate even when life is tough.

If you want to leave the 9-to-5 because you dislike your options there, or because it just doesn’t line up with how you want to live your life, those are better reasons. Construct a solid plan around those reasons and you might have found an exit strategy.

 

Just remember that the grass always seems greener on the other side. Those who feel trapped by employment might want any way out, but the opposite happens too: some entrepreneurs want the steadiness and structure back. On occasion, we choose the devil we don’t know—but, in doing so, we have to accept that we're taking a chance.

 

Two: Line up your allies

If your career is “getting places,” you can absolutely "build your own car" to do it; your brain and brawn are the engine, and registering the business creates the car’s body. But you’re still missing the car’s essential part: wheels.

An engine isn’t enough; you need a way to apply that power to the ground, or else you’re just making noise. The body doesn’t move itself; it’s just something to hold you (and the engine) while you drive. Wheels actually put rubber to the road; on a car, wheels are what turn power into progress.

In our analogy, your “wheels” are the people who give you traction with the rest of the world. They connect you with the people who can use and appreciate your work, who then compensate you for it. And you’re in business.

Every entrepreneur should have at least one mentor. Your mentor should be someone you can trust, someone who offers sound and selfless advice, and—not least of all—someone who knows a lot more than you. After that, networking is just a matter of what makes good sense for your business (and it’s good sense for everyone to network at least some).

No matter how much you trust yourself, never assume you can do it alone. You’re probably wrong. But even if you manage alone, you’re skipping out on tons of opportunity that was just waiting for you to say hello.

 

 

Three: Make a transition plan

If you know what you want to do, why you’re doing it, and who can help get the whole picture together, you have what you need to exit.

Timing matters, though. When and how should you officially leave the 9-to-5?

You should have a specific plan for transitioning to your new business. There are quite a few factors to take into account, but here are some you might not think about:

How long until your new venture can replace your old income? What if the new business doesn’t do as well as you expect?

How much money does the business need? How much does it need to open up shop? What kinds of unexpected expenses might pop up later?

What are your fallbacks? If certain things don’t perform well, what’s your plan for modifying or removing them? If everything goes south, what’s your backup plan?

 

Four: Start managing yourself

For the final time: we’ve all been a bit institutionalized. But even for the aspirationally-self-employed, understanding those institutions—like school and work—can be SUPER important to managing yourself.

Come on, you say. I know how to 'manage myself.' It's called life. I can handle being me.

We don't doubt that. But if you've never NOT had a boss, you're probably underestimating that person's effect on your behavior. The tedious, boring, frustrating parts of your job get done—whether or not you fully understand their purpose—because someone ELSE holds authority over you.

However aggravating (and sometimes cruel), this is a basic pattern for how groups of people accomplish big things throughout human history. 

It's near-impossible to (productively) punish yourself — even when you screw up and fully own it. In self-employment, the only consequences are natural consequences. You might not even know you screwed up until customers drop off—or until Uncle Sam comes calling. And when those problems come up, you don't have the option to pass the blame or the buck; you have to deal with everything.

Most people choose employment over self-employment for good reason. It’s easier to manage—or, more precisely, to be managed. 

So if you're going out on your own, observe what the established players get right, if only by necessity: structure. Structure is what you need to keep yourself in check—though remember, it's both art and science to manage yourself in this way, to create useful rules and routines that you'll actually follow. Remember, too, that structure relies on permanence and consistency—part of the reason you can't trust your head alone to keep the key details straight.

So write everything down. Keep notes, track the information most important to your success, and work things out somewhere that isn't your own head.

Not least important, always remember the best reasons you had for leaving the safety of the 9-to-5 world. Put it all on paper and you’ve just written yourself an exit pass to the most meaningful years of your life.

 

 

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