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The Twenty-Something’s Guide to Leaving the 9-to-5

Can't stand your 9-5 for a second longer? This guide is for you! Get started on your dream biz & lifestyle with this guide!

Until your early twenties, it’s pretty easy to be happy with standard options. As long as you have friends, pocket money, a little free time, and the classes you want, life is good. But once college is over and 9-to-5 life begins, the structured life won’t feel right anymore to some people.

Maybe it’s dawned on you: being an adult means that, as long as you pay my bills and taxes, you can do whatever you want.

Maybe you’re thinking about leaving your job and going out on your own. But creating a job isn’t a simple option; many people don’t know how to reason through that possibility.

If you want to figure it out, you’re in the right place. These are the four basic steps for creating your own job opportunity and leaving 9-to-5 life behind.

1. 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 those difficulties gets heavy. The right motivations, on the other hand, will keep you fighting and passionate even when things are 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’re taking a chance. 

2. Line up your allies.

If your career is “getting places,” you can absolutely build your own car to do it; you’re the engine, and registering the business creates the car’s body.

But you’re still missing the car’s essential part: wheels. The 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 help; it’s just something formal to sit in. Wheels put rubber to the road; they turn power into progress.

In our analogy, your “wheels” are the people who give you (your abilities and your intention) 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, you’re skipping out on tons of opportunity that was just waiting for you to say hello. 

3. 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 to start? What kinds of unexpected expenses might pop up?
  • 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?

4. Start managing yourself.

Let’s be real: we’ve all been institutionalized a bit. From grade school forward, we came to expect a boss, a schedule, and a to-do list.

Employment is the permanent adult version that pays you. There’s nothing wrong with that; most people choose employment (rather than self-employment) for good reason. It’s way easier to manage.

Becoming your own boss can be profoundly challenging, even if you’re motivated enough not to waste time. No one will correct you when you mess up. No one will praise you when you succeed. No one will show you the bigger picture and tell you to change course. No one will crack a whip and push you harder; no one will turn the lights off and tell you to go home. That’s all on you now.

The key to self-management—the key to all of this, really—is structure. It’s what works in a company; it can work for you.

Structure relies on permanence, so don’t try to keep everything in your head. Write everything down. Keep notes, track the information most important to your success, and work things out somewhere besides 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.


By Kevin Williamson | Code&Quill


Code&Quill began as a post-college experiment: can a couple of twenty-somethings design and sell the better notebook they’d wanted for ourselves? In January of 2015, Code&Quill’s first notebooks launched on Kickstarter to rousing success. In less than two years in business, they’ve sold thousands of notebooks to customers in more than 50 countries— and developed two new products along the way.

Code&Quill’s mission is to help creative people bridge gaps—between digital and analog, between potential and reality. The best tools help you do the best work.

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