Do You Have to Work For Yourself to Be Successful?

“I wish that I could work for myself.”

For some reason we tend to equate working for yourself with financial success. Many people will assume that being an entrepreneur means that you sit on the beach while the money rolls into your bank account (passive income) and that those with a 9-5 job are suckers for working.

Breaking news: being self-employed isn’t all that it’s cracked up to be. It’s not all about posting motivational quotes and telling everyone how to be passionate about their passions. Let’s look at the idea of working for yourself and if it’s the true secret to success…

Should you work for yourself?

When you tell someone that you work for yourself they assume that you’re rich. We have a tendency to think that people who work for themselves are well off. This is likely caused by the weirdos on Instagram singing the praises of passive income.

Yes, everyone can create passive income. No, being self-employed isn’t all about raking in the passive dollars.

There’s a huge difference between your own business and passive income. When you have your own company, you’re actively working for a living. Passive income comes from your investments (real estate or stocks) or your products (book sales or products that you don’t still have to work on) once you have a system in place.

When you’re new to personal finance/self-development/whatever we’re doing here or if you’re trying to figure this stuff out, there’s one thing on your mind. What is this?

You’re likely thinking about going into business for yourself to become more “financially successful.”

Do you have to work for yourself to be financially successful?


I want you to know a few things about working for yourself and being successful in life (whatever it even means to you to be successful in life).

  • You don’t have to be self-employed to make money.
  • You don’t have to work for yourself to get ahead in life (buy a house or travel).
  • You don’t have to share memes about being passionate about your passions.
  • It’s okay to work a job that you love.
  • It’s okay to work a job that you’re okay with but it pays the bills and lets you enjoy your lifestyle when you’re not at work.
  • You don’t have to sell an eBook on passive income to make passive income.
  • Working for yourself creates more issues most of the time since you’re in charge of bringing the money in.

You don’t have to quit your job after watching some Gary Vee meme to feel successful. You don’t need your own blog to feel like a winner.

This leads to the next point…

Working for yourself is totally overrated.

I’m here to let you know that working on your own projects full-time is totally overrated.

Why’s working for yourself overrated?

  • The work-life balance sucks. You work all of the time and don’t know when to stop. You feel guilty if you’re not working. You’re not sure when to take time off. You can’t just shut down at 5pm, on the weekends, and on vacation. You pretty much always have to be thinking about work.
  • Life’s easier when you have a steady paycheck coming in. My friends with steady jobs know exactly what they’re getting paid and when they’re getting paid. There’s no waiting for an invoice to be paid or hoping that the client isn’t behind. You also don’t have to chase your boss down for your check. Your income is likely directly deposited into your bank account.
  • Everything’s on you. You can’t phone it in or relax when you need money to pay the bills. You have to be on all of the time so that you can tackle everything in front of you.

You’re supposed to have the following when you work for yourself:

  • Set schedule.
  • Clear boundaries with friends and family.
  • Every productivity hack in the world under your belt (when in reality you just want to scroll through social media).
  • Some sort of highly efficient virtual assistant who doesn’t mind working for pennies.

What you really have when you’re the boss: headaches and confusion.

I’m not trying to discourage you from starting that business. I just want you to know what you’re getting into. There’s more to starting a business than sharing memes on social media about how you’re visualizing your success.

How can you get ahead without working for yourself?

You can get ahead by working at your job and saving money. You can invest in yourself to become better at your job or to move into another field that pays more. You can invest your money into property, stocks, and whatever else you’re into for extra money.

Here’s what to do if you want to get ahead without stressing about being the boss:

  1. Find a job that you really enjoy or can at least put up with. You don’t have to love every moment of your job. You can find a gig where you’re challenged and happy most of the time. No human being will ever enjoy every minute of work. The goal is to find a gig that you can put up with. If you hate your job, then that’s on you. Figure out a way to get into a different company or a new field. You won’t solve all of your problems by quitting your job to grow a blog on how passionate you are about pizza.
  2. Get into the habit of saving money. Are you saving money? To get ahead in life it’s important to always be saving and investing your money so that you don’t have to worry about where your next meal will come from or how you’re going to afford your mortgage payments. Try to put money aside. If you hate your job, then this fund will bail you out if you ever do quit.
  3. Plan some adventure into your life. Your life doesn’t have to be filled with adventure 24/7. Most of these people who you see on social media having fun aren’t actually always having fun. You can join a dance group, a new boxing gym, or try out different restaurants on the weekends to add adventure into your life. You don’t have to travel the world with a backpack to enjoy yourself.
  4. Do what you want to do. Stop comparing your life to unique bloggers. You don’t have to sell of your possessions to become a minimalist in order to feel good about your life. It’s okay if you enjoy your job because you get to live in a nice home and travel multiple times per yer.

I know that us bloggers can get annoying with this lifestyle stuff. You don’t have to live in an RV or be a minimalist to be a success in life. Success is different for everyone. It’s okay if you want to pay off your debt like Jacquelyn or go to Cancun every year.

Bonus tip: Try to make money on the side.

Side hustles are fun because you don’t have to stress about how you’re going to survive the lean months. This is money that you earn on the side to finance the fun stuff of your lifestyle or to save money faster. You can make extra money with driving for Uber or by just starting a fun little blog. I often write about making extra money because I want you to have more options in life. You don’t have to start a side hustle, but the extra cash flow helps to speed up your financial goals.

What could financial success look like?

Financial success is such a polarizing topic. To one person, being successful is about wearing expensive brands while going out for dinner every night of the week. To another person, success is about being able to quit their job to live out of a backpack while traveling the world.

What could financial success look like?

  • The ability to travel a few times per year. It’s pretty fun to go on a bunch of trips throughout the year. You don’t have to travel full-time to see the world.
  • Not feeling guilty about having fun on the weekends.
  • Paying off debt.
  • Cutting back on hours at the job.
  • Putting your kids in a better school system.
  • Being able to move out. Not everyone wants to live in a trailer or stay in hostels permanently.
  • Knowing where your money’s going. I’ve met readers who got into personal finance solely to see where their money was going.
  • A plan. A rough plan can go a long way for those days where you feel lost. Do you have a financial plan? Are you investing your money? Do you have goals? The beauty of a steady paycheck is that you can set goals and work towards them. A good friend recently purchased his second property. He enjoys his job and the opportunities that come with it. He makes money on the side painting to have extra cash for his trips.

Go out and chase your success. Whatever that means to you. Don’t let some weirdo on social media try to guilt you into quitting your job.

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