Are You Working Longer and Harder with No Happy Ending?

What are we doing this for?

We started businesses because we wanted to make more money, but it doesn’t take a lot of deep thought to realize that it was only the most superficial of motivations.

Whether it’s because we have a mountain of debt, because we want to retire early, or because we’re looking for some financial freedom from the day job, the underlying motivation isn’t merely a better financial picture, but a better life.

Fact is, if you started a side-hustle or solopreneurship for any reason other than to make your life better, you’re doing it for the wrong reason and it probably isn’t going to work.

I joined Instagram a while ago and spent some time looking around the entrepreneurial community there. I was turned off pretty hard and pretty fast.

Much of the “discussion” was merely a bunch of cheap sloganeering. I chalk that up to the nature of the platform, but it wasn’t my real problem. That was the cadre of posters who fetishized the grind.

There are times in any industry that require longer hours. I used to be in IT and long days leading up to a release were the norm. Accountants go crazy at tax time. Journalists have daily and weekly deadlines. Every project has an ebb and flow of labor and that’s normal and healthy.

What isn’t healthy is focusing on the grind to the exclusion of the rest of your life. If you’re continually grinding for any other reason than that you’re teetering on the brink of survival, you’re going to burn out and it won’t be pretty.

If You Want to be Happy, You Have to be Free

Do you know that Monday morning feeling where you’d rather pluck out your eyeballs and eat them than go to work?

Of course you do.

Have you ever thought about why you feel it? On the surface, it’s because you don’t like your job, don’t like the people you work with/for, or don’t find the job rewarding. You don’t have to think hard to find better ways to spend your time.

I think that if you look a little deeper, you’ll find something revelatory.

When you get that Monday morning feeling, you go to work anyway, don’t you? You have bills to pay, maybe a family to support, and you need to bring in a paycheck. You don’t feel bad about these obligations. They are—if you can pardon the sexism—a man’s job. It’s hard, but it’s satisfyingly hard because there’s a larger purpose behind the labor.

And that, I think, is the source of that Monday morning feeling. You feel like your labor is disconnected from the underlying purpose. You go to work, do what someone else says, make someone else rich, and get a paycheck so you can pay the bills.

Years ago, I was reading about how to make software packages more palatable to customers because that’s just how exciting my life was. One of the few things I took away from that was the notion of control.

If you give users the ability to customize their software—even things as trivial as changing the color scheme—it will make them feel like they have more control, thus making them more comfortable.

It turns out this concept of control and comfort is one of the key drivers of happiness. Life is often a big, complicated mess over which we have little control. Establishing even a little control—taking a single action to fix a problem—can have an enormous effect on how we feel even if the problem hasn’t been solved in its entirety.

That Monday morning feeling is rooted in a lack of control over what you do. When you’re not free to choose what you work on, you’re not as happy as when you do get to choose even when the work is the same.

In many ways, choice is happiness.

If You Want to be Free, You Have to Work

They say money can’t buy happiness, and while there’s a certain degree of truth in the adage, most of it is bullshit.

When you’re being hounded by bill collectors, having the money to pay them would make you happier. When your kid wants to play soccer, having the money to pay the fee would make you happier. When you’re tired and frustrated and want to get the hell away from the world for a while, having the money for you and your partner to see a show and have a nice dinner would make you happier.

When you don’t have enough of it, money sure as hell can buy happiness.

That’s because with money comes control. You can buy yourself out of harassing phone calls. You can treat yourself to the better things in life. You can make sure your family can pursue their passions.

But you can’t make money by sitting around doing nothing. I know. I’ve tried. It doesn’t work.

You’re going to have to work. You’re going to have to work hard. And you’re going to have to do things to you don’t particularly like to do.

I have a pretty cool job. I sit at my desk and I write stuff. I can do it in my underwear. I can do it in a coffee shop. I can do it in a van down by the river. It’s a great job.

But it’s more than just sitting there writing. I have to know what to write, and that means I have to do keyword research. That’s researching the actual words and phrases that people use to talk about the stuff I want to talk about. It’s why I use words like “side-hustle” and “solopreneur” even though they’re trendy buzzwords that make me want to eat my spleen.

I hate it. Loathe it. It’s all poring through thousands of keyword phrases to find out what’s being used enough but not too much. I end up with a mishmash of long-tail phrases many of which don’t make any damn sense in a real-world context. I despise it.

But it’s part of the job. It’s how I do the job well. It’s how I can make informed choices to write posts and articles that will make more money for my clients and myself. It is directly connected to the underlying purpose of doing the job. When I choose to do keyword research, I know I’m choosing to make more money, have more control, more freedom and, ultimately, be happier.

The Happy is More Important than the Work

Ever wonder why you keep seeing tech zillionaires trying to recreate stuff we already have, putting cars in space, and generally doing a bunch of whack-ass shit?

It’s because they’re rich as hell and having nothing to do every day gets very boring very fast.

We want to do something with our days that feels meaningful. For a lot of us, going to a job we don’t particularly care for so we can take care of our family is meaningful enough. That’s fine.

A lot of us want something different. We want to make something. We want to forge our path, test our ideas, and make a difference in our lives if not the world.

That’s also fine. It comes with more risk, but if you’re not putting your family’s welfare in danger, it’s better than fine.

Regardless of which path you’re on, it’s easy to let the means overcome the ends.

It’s easy to get caught up in climbing up the corporate ladder. It’s easy to think that if you just put in some extra time, the boss will notice and you’ll get that promotion. But unless you’re the boss, there’s always another promotion. There’s always another project you can spend extra time on. There’s always another carrot.

Similarly, when you’re an entrepreneur, there is never a second of your life that couldn’t be spent working on your business. Not when you’re awake. Not when you’re asleep.

But the means aren’t the point. The ends are, and the only end that makes any sense in this life is happiness.

That doesn’t mean you fulfill every whim every day. It means you make commitments that mean something to you. It means that you honor those commitments and the concomitant responsibilities.

It means you do the icky stuff so that sometimes you can do the whimsical stuff—like using the word “concomitant” just because it amuses you. [eta: I run all posts through Grammarly before I post them and Grammarly didn’t like “concomitant” at all, but it’s still there, isn’t it?]

We Buy Happiness with Effort and Time

The things that bring you joy are worth your time and effort.

Your family is worth your time. Your hobbies are worth your time. Your passions are worth your time. They make you happy and that’s a good thing.

Figure out how to make money in a way that fits your skills and ethics. Work hard at it, but don’t let it consume you.

Figure out what makes you happy. Develop a new skill for no other reason than that you want to make pretty things. See movies for the sheer exhilaration. Watch your kid’s play or game. Coach their team. Go on date night with the wife.

Spend time and effort to be happy because one day we’re gonna die.

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