📺 Stream EntrepreneurTV for Free 📺

5 Things No One Tells You About Working for Yourself Having worked for myself for over six years, I'm sharing the taboos no one tells you when you set up on your own.

By Laura Stupple

entrepreneur daily

Opinions expressed by Entrepreneur contributors are their own.

Congrats: You're considering working for yourself or have already started doing so. Welcome to the most exciting and exposing experience of your life. Running a business is like holding a mirror up to yourself; there's so much you're going to learn.

It takes oodles of courage, some solid knowledge and a dash of optimism to start working for yourself. Plenty of us dive in head first without knowing what to expect.

There's a lot that doesn't get mentioned when people talk about entrepreneurship, so here are some of the things you might not have heard about working for yourself.

Related: The Simple Recipe For Being Your Own Boss: Vision + People + Systems

You'll have the best of times, you'll have the worst of times

Get ready to experience a kaleidoscope of feelings — and that's just in the first week.

From fear to dread to pure excitement and bliss, you'll feel it all. When you're working for yourself, there's more pressure than you can imagine. But this pressure feels very different to employment.

You'll no longer have anxiety about whether your colleagues like you, if your boss saw you take an extra 10 minutes on lunch or whether you're going to get assigned a boring piece of work. None of that matters anymore, because you're in charge.

When you work for yourself, you'll worry about more primal needs like how you'll pay the bills that month or how you're going to eat. At the start, this financial pressure can break you.

My advice? Romanticize the hustle at the start as much as possible. Lean into the stress, long hours and low income. It's part of the process and doesn't last long. Unless you resist it — then it lasts forever.

You'll say yes to everything at the start (and it will become problematic)

You'll be such a yes man/woman that people will start confusing you with Jim Carrey.

It would be so much more fun if you could skip this step, but from my experience, no one does. The raw excitement of running a business gets the better of everyone, and whether it's out of joy, people-pleasing or sheer desperation, you'll inevitably end up saying "yes" to work you really shouldn't.

More often than not, this looks like accepting projects that are below your pay grade — but it might also look like adapting your offering in a way that compromises the quality of your work or working with clients that don't align with your values.

In the first six months, you'll say yes to everything. After that, you'll learn the word no, and it'll save your life.

Related: The 'I'm My Own Boss' Myth Humbles Many an Entrepreneur

The flexibility is amazing, but you'll probably abuse it

You get to do whatever you want.

No, really. There are no rules, apart from having to pay taxes. The flexibility when you work for yourself is amazing. You can take time off whenever, travel when you like and spend more time doing the things you love.

People tell you that though, right? This article is about the things people don't tell you — and what they probably don't mention is that you'll probably abuse this privilege.

You'll likely find yourself starting strong — the first couple of years you'll have a great routine, the hustle will be on and you'll spend more time working than doing anything else. But as soon as you start becoming successful (by your own standards), you'll find it hard not to abuse the privilege of flexibility.

You'll have late nights, luxurious lie-ins and spontaneous trips away whenever you feel like it. And who's to say you can't? It's your business.

But after a time, it becomes hard to rein yourself in and get back to the routine that made you successful in the first place. With no manager and no one to answer to, you'll most definitely go a little rogue from time to time.

You become pretty much unmanageable

Maybe you always were "unmanageable," and that's why you started your own company. Either way, no one tells you that you'll become unmanageable.

Mentored? Yes. Collaborated with? Yes. But managed? Nope.

Once you've worked for yourself for a few years, it can be incredibly hard for people to manage you. All that time managing your own schedule really shows, and your ability to set boundaries makes most managers feel like you don't respect their authority. Your laser-like focus on outcomes and bias for action will make it hard to ever work 9-5 again.

You'll either find this out by going back into employment or taking on a client who (wrongly) thinks you work for them. Don't do it.

Related: You'll Be Your Own Boss: Really? Busting 5 Misconceptions Of Entrepreneurship

You'll earn more than you think and it'll feel worse than you thought

This is probably the most controversial thing that no one tells you.

You're going to earn more money than you'd ever imagined possible when you were in full-time employment. Your world will open up in a way you didn't even know existed.

Not having to worry about money is a blessing many aren't afforded in this life. And for the first couple of years, you'll feel gratitude for this every day. But once this flow of income becomes the norm, you'll feel unsatiated once again.

The same feeling that drove you to start a business in the first place returns with a vengeance. The niggling thought that you're not doing enough returns. And whilst you can reflect and see that you've had success, it never feels like enough.

The goalposts have moved. You need more. And honestly, I don't know if that feeling ever goes away.

Your weakness is your superpower

Jump in. Enjoy the ride.

But don't believe you'll feel more successful, don't think you'll feel more accepted by others and don't believe you'll be more satisfied than you already are now.

You won't — and that will be your superpower.

Laura Stupple is the founder of LJS Content, a marketing agency in the U.K. and Australia. She crafts award-winning content for brands like Bloom & Wild, T2, Gillette, WestPac and more. When she’s not writing, you’ll find her in the boxing ring or sipping coffee and watching the world go by.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Editor's Pick

Business Ideas

63 Small Business Ideas to Start in 2024

We put together a list of the best, most profitable small business ideas for entrepreneurs to pursue in 2024.


Franchising Is Not For Everyone. Explore These Lucrative Alternatives to Expand Your Business.

Not every business can be franchised, nor should it. While franchising can be the right growth vehicle for someone with an established brand and proven concept that's ripe for growth, there are other options available for business owners.

Business News

Passengers Are Now Entitled to a Full Cash Refund for Canceled Flights, 'Significant' Delays

The U.S. Department of Transportation announced new rules for commercial passengers on Wednesday.


Why Companies Should Prioritize Emotional Intelligence Training Alongside AI Implementation

Emotional intelligence is just as important as artificial intelligence, and we need it now more than ever.

Business News

Elon Musk Tells Investors Cheaper Tesla Electric Cars Should Arrive Ahead of Schedule

On an earnings call, Musk told shareholders that Tesla could start producing new, affordable electric cars earlier than expected.