Ah, quitting your job. Don’t tell me you’ve never fantasized about it – storming out of your boss’s office, maybe telling off an annoying coworker or two, and walking away with your head held high, never to return to that dreadful place of employment again.

“When I’m making millions in my own business,” you think, “they’re going to feel like idiots.”

Many people dream of doing it, but few actually take the plunge. But, will quitting your job to start your own business actually improve your life?

If you’ve been thinking about waving goodbye to your 9-5, there are some things you have to understand first. 

To illustrate these points, I’m going to tell you my story.

My story

I quit my job in December 2021 because I wanted the same things most people do when they start their own business—more money, more time, and more independence. Most people assume that those things will make them happier. The question(s) they fail to ask themselves is this: 

• Does more money make you happier?
• Does more time make you happier?
• Does more independence make you happier?

I’ve been without a job (at least in the traditional sense) for almost two years now, and I can tell you, the answer for all of those questions is: it depends.

It depends on how you use your additional money/time/independence.

Does having more time make you happier?

I’m here to tell you that working less doesn’t intrinsically make you happier, and by extension, having more free time doesn’t intrinsically make you happier. 

However, having more free time does give you more opportunities to fill your life with things that make you happy. 

When I first started working as a freelance editor, I was still working about 18 hours a week as a teacher’s aid at an elementary school. I would work at the school in the mornings, come home and have lunch, then do a few hours of editing. After a few months of that, I decided to quit the elementary school job and just pick up more freelance jobs. I figured that I could get more editing work done, plus have even more free time. 

The problem was, I’m not perfect at managing my time or disciplining myself. 

On some days, I’d stay in bed for too long, drag my feet about getting up, and watch several more YouTube videos than I planned to. By the time I actually started working, it was practically lunchtime, and I might as well have gone to work at the elementary school.

I had more time, but I wasn’t using it well.  

Lazy mornings are occasionally just what the doctor ordered, and I definitely have them several times a month. But by and large, they don’t make me feel great when I have them everyday. 

The thing is, I didn’t need to start working first thing in the morning to feel great about how I was using my time. Going on a morning hike, making muffins while listening to a podcast, or eating breakfast outside while reading a book were all things I did in the morning that made me feel AMAZING. 

Those things weren’t necessarily productive, but they were things that made me happy. Those were the things that made me glad I didn’t have to get up and go to my old job. 

Does having more money make you happier?

What about the extra money? Did that make me happier?

Well, to be honest, I wasn’t making a ton of “extra money” when I first started working for myself. But let’s say I was. Assuming that my needs were comfortably met, extra numbers in my bank account wouldn’t automatically boost my mood. 

“Money doesn’t buy happiness,” they say. But I’ve also heard, “If you think money doesn’t buy happiness, you’re spending it wrong.” 

The bottom line is, there is no point in earning extra money, which most people want to do, if that money doesn’t change your lifestyle in some way. 

Money is meant to be spent (just not all of it—saving and investing is essential. You know that.). The key is spending it in ways that actually improve your life.

Does having more independence make you happier?

Did having extra independence make me happier? 

Once again, it depended on how I used it. Like I mentioned before, if I stayed in bed watching TV all day, I might have an initial rush of, “oh this is so nice. No one is making me get up and work.” But that good feeling doesn’t last all day, and it certainly doesn’t last for weeks. That would NOT be a good use of my independence. 

Managing my time is something I used to struggle with, and I’m still not perfect at it. I’m a huge procrastinator, and I’m well aware of how easy it is to get distracted by this little thing called The Internet. 

Working for yourself requires you to discipline yourself. 

Honestly, sometimes it’s easier to have a Big Boss to blame for making you do all the work. When your Big Boss is yourself… it’s easier to be lenient.

Having independence over when and how much you work won’t make you happier if you don’t have discipline, because you’ll constantly feel guilty and stressed about the work you’re not doing.

On the other hand, if you give yourself too strict a schedule, that won’t make you happier either. I strongly believe that you should create a flexible enough schedule that you can take a break when your mind and body needs it. 

As a freelance editor, I got paid by my output—by how many words I edited, not by how long I spent editing them. Editing is mentally tiring, because it requires huge attention to detail. Without fail, after working hard for an hour or two, I could feel my mind start to get tired. 

I knew that if I pushed through and tried to keep editing with a fatigued brain, the quality of my work would suffer. Completing orders would take me longer than it would if my mind were refreshed. 

So, the minute I started to feel my mind slow down, I would give myself a break. I’d go on a walk, read a book for fun, work on a different project that didn’t take so much mental energy, and I’d only return to the editing work when I was feeling refreshed.

That’s the kind of independence that made me happier.

So, what causes true happiness?

The concluding thing I want to mention is that if you’re waiting for a life event (like quitting your job) to come along and magically make you happier… well, you might be disappointed.

Notwithstanding very real issues like depression, trauma, poverty, etc…. You can choose to be happy no matter what your circumstances are. 

If you’re the type of person who is miserable when you have a traditional job, I’m sorry to break it to you, but you aren’t going to magically be happy all the time when you quit. 

In fact, there are a lot of reasons why quitting your job might make it harder to be happy, like the stress of not having a regular paycheck, the guilt that comes from having to discipline yourself, and the loneliness of not having coworker friends that you see every day.

But if you’re the type to want to be happy, to actively pursue things that bring you joy and discard things that bring you down, quitting your job might be a way that you chase that happiness you crave.

Conclusion

So, if you’ve been thinking about starting your own business to have more time, money, and independence, remember those things only make you happier if you use them well.

As for me, I wouldn’t say quitting my job made me happier. I would say that I chose to be happier, and quitting my job to work for myself was a natural consequence of that. 

And I’m glad I did it.

So, what about you? Have you quit your job (or are you dreaming about it)? What would you do with some extra time, money, and independence?