Is a Steady Job Really Security? 12 Years of Pay Bills and Die

Adapted from the Command Podcast episode “I Spent 12 Years Calling This ‘Security.’” Watch the full episode above.

The night in the hotel room

About 10 months ago I was sitting in a hotel room, working out of town like I was 200 nights out of the year. Working 16-hour days. Sixty to 80-hour weeks most of the year.

For 12 years, from the time I was 18 to 30, I ran a 70,000-pound asphalt milling machine.

The week before, I’d started 75 Hard. I said, “I need a hard standard reset. I need to prove to myself that I can keep my own word again.”

That day we worked from 6:00 a.m. until about 9:30 at night. By the time I fueled up and did all my maintenance on my machine, I got back to the hotel around 10:00.

I’d worked out in the morning, but I didn’t get my second workout in. I failed 75 Hard. I also broke my promise to make at least 20 cold calls for my real estate business, because it was too late to call anyone.

I just sat there questioning why.

When does postponing your dreams become giving up?

I was a hard worker, a team player. I was one of the best operators at the company. I showed up, didn’t take days off, and did good work. How you do one thing is how you do everything.

But I had dreams way beyond that job. Being an entrepreneur. Having a lake house. Getting my pilot’s license and buying a little plane.

That night I started asking myself: when does postponing that become giving up on your dreams?

I’d been chasing the security of the paycheck unintentionally. One day at a time, putting it off until tomorrow ended up being 12 years later. I never planned on doing heavy equipment forever.

I grew up in a rough situation. My father passed away from drinking when I was 16. I lived with gang members and drug addicts. I was going to join a gang when I was 18, because those were the only people I had to look up to.

When I turned 18, I decided a real man works. A real man supports his family. A real man makes something out of himself.

But that night I realized I’d gotten caught up in putting things off until tomorrow. Caught up in “I’m still in my 20s, I’m still young, I’ve got time.”

When I hit 30, I was still doing the same thing I was doing 12 years ago. Yes, I was further ahead. I was stronger. I’d grown. But I was more miserable, because I realized that if I did the same thing I’d done the past decade, I’d turn 40 and look back on my 30s and say, “Damn, I wish I’d taken a chance on myself. I wish I’d quit chasing the security of a paycheck to Pay Bills and Die.”

That’s what kept going through my head. Pay Bills and Die. Pay Bills and Die.

Is a steady job really security?

I had a great-paying job. Double retirement. Full benefits. All the stuff that’s supposed to make you happy. Everything most people would be happy to have. I bought my first house when I was 20.

But honestly, none of that really mattered to me. What mattered was my health, my happiness, and spending more time with my wife. For the first nine years of our marriage we didn’t get to spend much time together, because I was out of town eight or nine months of the year.

And every year I’d fall off. I’d get the better part of three months off, quit drinking, and work out every single day. Then work would hit and I’d slowly taper off until I was drinking almost every day again and barely working out.

I’ve started multiple businesses but never got any of them off the ground. I had a track record of doing some things, but not following through on the things that mattered most. I could do the physical things, but I could not execute on the business. I think a lot of that was fear. I didn’t want to look bad at something.

I had so little energy after breaking promises to myself that I started losing trust in my own word. That hurt more than anything. Every year I was starting over from scratch.

When you have 10 years of evidence that doing more of the same is not going to lead to a different result, it’s time to change what you’re doing.

Betting 100% on 1% belief

My wife believed in me more than I believed in myself. All that last year she kept saying, “This is your last year. This is your last year.”

I’d think, yes, but there are bills to be paid. You can’t just walk away from a double-retirement job with full benefits. She needs health insurance.

That night, I finally thought: maybe she’s right. Maybe life isn’t meant to be lived for security. Maybe it’s meant to go have experiences and tap into the potential you know you have within you.

So I changed my relationship with security. Instead of having security in an outside entity, a paycheck that comes as long as I show up to work, I decided the security is within me. In my actions. In my execution.

I still didn’t really believe in myself that much. I had maybe 1% belief that I could make it happen. But I bet 100% on that 1%.

That Friday I put in my two-week notice and quit the career I’d had for 12 years. All I had really ever known.

Ten months later, I have 100% belief that I can do what I say I’m going to do. If I can do it, you can too.

What happened after I quit my job

You’d think everything was sunshine and rainbows after that. Honestly, it was not. It was really tough.

At a job, you get paid to learn how to do it. In entrepreneurship, you don’t get paid to learn. You get paid when you actually execute well.

I already had a bunch of knowledge. The sales scripts, the marketing ideas, the business tactics. What I didn’t have was execution. Once it got hard and I had to do the uncomfortable thing, like making the calls and making the sales, I’d decide, “This isn’t what I want to do. Let’s do this business instead.” That’s just another form of self-sabotage and procrastination.

So I realized I needed to change inside more than I needed more knowledge. I needed to work on myself harder than I worked on the business. I needed to dig up the root causes of why I was the way I was: the procrastination, the victimhood, always asking, “Why me? Why is this happening?”

After I quit, I had crippling self-doubt for a while. So I reflected on my life. I’ve lived out of my truck for six months. I’m still alive, still here.

I told myself: I’ve always had enough. I have enough right now. And I will always have enough. That’s what helped me break through the self-doubt.

Do you need to quit your job?

For everybody, it’s not quitting your job right now. This isn’t me telling everybody they need to quit.

For me, it was required. I needed to be in control of my time and myself. I had over a decade of evidence that what I was doing was not going to lead to a different outcome.

Your path right now, if you’re not happy with where you’re at and you’re having trouble keeping your own word, might just be keeping that next promise to yourself. Maybe it’s as small as brushing your teeth. Maybe it’s working out in the morning or making your 20 cold calls for the day.

Whatever it is, keep that promise for the next seven days. Keep it small enough that you have no problem following through.

The silent surrender

Nothing had to fall apart for me to make that decision. It wasn’t one big moment where everything came crashing down. It was realizing, over the years, that I was putting it off until tomorrow.

It’s what I call the silent surrender. A lot of men are living in misery with a smile on their face. They know subconsciously that they’re silently surrendering their potential and their dreams to the day in and day out. They’re forfeiting what they know they’re capable of to laziness, vices, cheap dopamine, and saying “tomorrow.”

Tomorrow always sounds better than doing it today. But tomorrow is just enough to take the sting off of not doing it today, and you’ll postpone your life until you’re looking back on it with regret.

So next time you say, “I’ll just do it tomorrow,” use that as a trigger. Tell yourself, “Tomorrow is where dreams go to die. Today is the only time I have to move forward.” Then choose to execute today. I don’t care how small it is.

Ask yourself: if the next 12 months look exactly the same as the last 12 months, where will you be? How will you feel looking in the mirror and telling yourself, “I changed nothing”?

The time to change is today. Not tomorrow, not Monday, and not next January.

One kept promise at a time is how you build self-respect and the confidence to go out and conquer your goals and dreams.