Why I’m Happier Leaving Thousands of Dollars on the Table

Josh Hoffman
Epic Freelancing
Published in
4 min readMar 21, 2017

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Credit: Unsplash / Morgan Sessions

At some point in your life, I’m sure you were led to believe more money, more happiness.

At least I was.

Actually, there are studies that suggest a negative correlation between the two, but I’m not here to talk about data. Math was never my favorite subject. For one thing, I’m not very good at the whole numbers game, which is probably why I don’t like it. We generally like what we’re good at, right?

But, here’s the thing: If I learned to like numbers and data, I’d be generating 10 times the amount of money for my digital marketing business.

“I’m wondering why you don’t want to do ads?” my friend Victor recently asked me. “That’s where the money is. Hourly is great and stuff, but online advertising is where you can get a monthly retainer plus commission, which basically means there’s no limit on what you can earn. That’s how you can go from a $5,000 project to $50,000.”

Victor is totally right. I could be making a lot more money, but would I be happier? HECK NO.

The mark of success, as a freelancer and otherwise, is not money. It’s personal happiness.

It’s knowing you have the freedom to do what you want, when you want, how you want, where you want, with whom you want, and as much as you want. It’s doing something for as long as it’s fun, and then moving on when it stops being fun, because you have the control to do so.

So, yes, I’m not making hundreds of thousands of dollars like many of my online advertising friends. BUT, I live and travel wherever I want, whenever I want, because I can work from anywhere with WiFi (including poolside in Thailand).

I have total control of my schedule, which for me means not working on Fridays, and not taking phone calls or meetings before 11 in the morning. (I’m not exactly what you would call a “morning person.”)

I pick and choose my clients based on who can afford my rates (I just raised it from $100 to $120 an hour) and who wants to work on my terms. I don’t take on projects I don’t want to do — because I’m not desperate for the money — and I get paid very well for projects in my wheelhouse.

Oh, and by the way, I still make really good money relatively speaking.

But, I didn’t get to the promised land of personal happiness overnight. Instead, it took years of doing things wrong — because I was chasing money — to learn how to do things right. In fact, it got so bad, I almost lost my entire business and fell into a two-month depression that ended my two-year relationship. (I’m single again, if you know anyone. Haha, just kidding. But yeah, I’m single.)

I learned the hard way that the best way to achieve personal happiness is through self-awareness.

It starts with a self-awareness inventory: an outline of your passions (what you like), your pains (what you don’t like), your strengths (what you’re good at), and your weaknesses (what you’re not good at).

The key to self-awareness is twofold. First, you need to be totally honest with yourself. It can be difficult to look yourself in the proverbial mirror and admit you’re not good at certain things, but the more honest you are with yourself, the happier you ultimately will be.

Then, double down on your passions and strengths, and create a symbiotic relationship between the two — only these two. In other words, ignore your pains and weaknesses. Don’t try to improve upon or cope with them. Just don’t worry about them, and don’t offer services that somehow require you to do things you don’t like and aren’t good at.

In my case, this meant exclusively offering high-level digital marketing strategy and consulting (my strength and passion), and no longer offering ongoing social media management and content creation (my pains, because they’re tedious and mind-numbing). Even though I can outsource these day-to-day tasks to other freelancers (which I’ve done in the past), I’m not very good at managing people (my weakness), so it became one headache after another.

And yet, for all the money I’m leaving on the table — because I’m not offering online advertising services, and I’m no longer outsourcing day-to-day tasks — I’ve never been happier with the work I’m doing.

Was it easy to get to this point? Absolutely not. But as I know you know, nothing worth it is easy.

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Founder of IZZY – Stream Israel, basketball lover, mental health advocate