A Brutally Realistic Guide To Your “Dream Job” Of Working For Yourself

Here’s how to nail the “living” part of “living the dream.”

A Brutally Realistic Guide To Your “Dream Job” Of Working For Yourself
[Photo: Flickr user Manuel Martín]

When many people are asked what their “dream job” might be, the answer often involves becoming their own boss. It often doesn’t matter in what field–the main allure is no longer having any superiors to answer to. In fact, according to one recent study, 29 million Americans are considering going independent in the near future. But it’s a pretty fair bet that not all of them will.


That’s understandable. There’s no one formula that makes being independent work for everybody who tries it. But one of the trickiest hurdles is to translate your “dream job” notion of self-employment into a sustainable–and still personally satisfying–reality. Here’s what that takes.

1. Expect Your Expectations To Change

Perhaps the hardest lesson most independent workers learn is also one of the first that they face: That your “dream job,” whatever it consists of, takes hard work to realize and usually isn’t what you thought it would be once you’ve finally realized it.

You’ll have to overcome decision fatigue as you make choice after choice, often without much experience or information to go by. You’ll learn how to set priorities, and value and price your work. Plus–and perhaps most arresting of all–instead of one boss (yourself), you’ll actually have several, in the form of clients, each with their own requests. Paradoxically enough, having control over everything in your professional life can be thrilling and paralyzing at once. And after the initial euphoria of self-employment wears off, you may worry that you made a mistake.

The knowledge you acquired in order to become an expert in your field isn’t the same as the skills required of a business owner. Learning a whole new skill set is likely to make you feel incompetent. That can lead to self-doubt, which can tank your entire effort if you aren’t careful. Bear in mind that this anxiety is normal and temporary.

Getting past it, though, takes recognizing that once you have settled into independent work, you probably won’t describe it as your dream job–but you’ll still enjoy it. Most independents find that after mastering the practical realities of working for themselves, they wouldn’t trade it for anything.


2. Save Up, And Prepare For A Bumpy Ride

Building a sustainable business doing exactly the kind of work you want to do takes time. Your first clients and projects may not be ideal. Give yourself plenty of financial runway. While reducing your debt is critical, having cash on hand is actually more important for independents. This might sound counterintuitive. Obviously, having no debt is ideal but isn’t always practical. Money in the bank makes you feel less desperate so you don’t have to take just any prospect that comes your way.

Soon after going solo, you may also find that you need to pay off debts at a slower rate than you’d like while building a solid financial base. Having cash reserves helps here, too. That helps you ride out the natural fluctuations you’ll inevitably meet with in the early stages of business. This way you won’t find yourself white-knuckling it with a carton of ice cream in one hand and the other furiously tapping your keyboard as you search the internet for a job.

3. Lean Hard On Your Strengths And Assets

Most aspiring solopreneurs’ daydreams don’t feature the fact that everything–including bringing in revenue–rests squarely on our own shoulders. Selling is a new skill for most independents. It’s easy to rely on your existing contacts for those initial clients, but when the friend well runs dry, you may not know whether to go to events, adopt a content marketing strategy, start a blog, or all of the above.

Trying out an array of business-building methods for the first time can drain you. While there are some general recipes for business success, the specific strategies that work vary tremendously from person to person. So take time to think about what you naturally enjoy so you can apply those skills to the type of promotion you’ll need to adopt.

This goes for other parts of your business, too. Know your strengths and put them to use–including in functions for which you may not have applied them yet. Then automate or outsource tasks you hate or just aren’t good at, as well as scheduling, building a website, or writing copy as the case may be. Just because your business’s success or failure is all on you doesn’t mean that every single task needs to be done by your own two hands.


4. Take Time To Get To Know Yourself (All Over Again)

One of the biggest surprises for independents is finding ourselves sitting at home, unsure how to proceed.

Untethered for the first time, and having to create all the rules from scratch, can be disorienting. You may begin to realize how much of your career and work style has actually been dictated by someone else. Many of the norms of 9-to-5 work are vestiges of the Industrial Revolution, and reflect the exigencies of factory management more than those of 21st-century knowledge work. The work habits you’ve fallen into may not serve you so well when you’ve dramatically changed the context in which you’re applying them.

To adjust to being taken off autopilot for the first time, keep asking yourself these four questions. It’s okay if the answers change over time–the key is to gradually get reacquainted with the new, self-employed you:

  1. Are you best in tiny bursts throughout the day or long stretches that begin at a certain time of day?
  2. Do you work best in total silence or amid the hum in a coffee shop?
  3. Do you need to go into an office, or are you disciplined enough to avoid distractions at home?
  4. What depletes your energy?

Finally, don’t be disillusioned if working for yourself doesn’t look exactly as you expected. We tend to build up our “dream jobs” to such a degree that some measure of disappointment may be inevitable. But it doesn’t have to do you in.

Once you understand your main assets and how to get the best out of yourself, your work will come pretty darn close to the stuff of your dreams–and way better than wishing for a different life.