A career is a series of games – you just have to figure out which ones are worth playing

A career is like a series of games.

Assess what games are wroth playing with a series of questions – outlined below.

A quick sponsored note before we dive in:

As you know, we’ve got 18 employees working at our self storage management company who live in the Philippines. We sourced and hired all of them through SupportShepherd.com. and it has been a game changer.

They do customer service, collections, data entry and even direct customers around our properties to find their units. They are incredibly valuable members of our team that allow us to offer 24/7 service (and more reps) at a low overhead cost. Each employee starts at about $800 per month or $5 per hour.

I’ve personally convinced about 10 of my friends who are business owners to make a hire over there in the past year, and they all have told me it has changed the trajectory of their business and their life. Check out Shepherd. today.

The key to winning is taking a step back early on and figuring out which game is worth playing and which one isn’t. Too many people play the wrong games with stiff competition and shitty prizes and wonder why it’s hard AF to get ahead.

Is your goal to make money and so you can quit trading your time for money as soon as possible? If so, this email is for you.

Is this game fun to play?

If so, you’ll get a lot of people playing the game for fun and not for money. And it likely adds value to you and doesn’t add much value to others. People play it for selfish reasons. Don’t play against these people because they’re irrational.

How good do you need to be to win? What percentage of the players accomplish your goal of financial freedom?

Pro sports are one extreme. .5% of folks who try to win this game get paid well. Sweaty startups are on the other end. A lot of dumb people make a lot of money in boring businesses.

What does winning look like?

A corner office and good-enough pay but no life and 70 hour work weeks? Look at your boss and their boss. Do they enjoy their lives? That’s where you’re headed if you win.

Who are you trying to impress?

Are you going a direction because others think you should or society idolizes it, or because it makes you more likely to accomplish your goal? Your ego is the enemy when it comes to choosing your game.

Does the game reward the right kind of action?

Too many folks get burnt out in many fields because they’re more about politics and less about adding real value. If you’re a politician play the game. If you want to be rewarded monetarily for value, avoid the bureaucracy.

Do you want it all right now?

You’re destined to fail no matter what game you choose. The folks who win think 5 years ahead. They delay gratification. They do the sucky work now so they can do the fun work later.

Can you avoid the golden handcuffs?

Because when you start earning more (and working more) most folks spend more. And they become addicted to the paycheck. Totally dependent. If it stops, even for a little while, they’re under water.

Can you shift gears once you’ve “won”?

You’re rich. Do you keep grinding 70 hrs a week? Do you take a step back and enjoy your children? Do you change your investment style and de-risk? Or do you keep pushing it all back on the table and go broke?

The winners have balance. They’re like water. Changing course when a path of least resistance becomes available. They’re opportunist. They quit when the odds suck. And double down when the odds are good.

The winners took a few steps up 20 different mountains.

Took a look at what life at the top was like and how hard it would be to get there. And then picked the one that was worth climbing.

Onward and upward,


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About Me

I started the Sweaty Startup in December of 2018 because I believe the Shark Tank and Tech Crunch culture is ruining the real spirit of low-risk entrepreneurship.