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  • Writer's pictureDillan Taylor

Is $50k/month actually possible?

I took my little brother rock climbing a few weeks ago. He's 17, taller than me, and makes me look like a skinny child.

He loved it. We got him a membership and he and I climb three or four times a week now.

I'm not a great climber. I started going with my friends last year hoping to combat my fear of heights. I've gone inconsistently since then and have become a decent beginner.

There are many things I love about the sport. But one phenomenon fascinates me above everything else.

I call it the climber's insight. Let me explain.

Many routes are too easy and you flash right to the top. Most routes are too difficult and you can't even make it past the starting point. It's the routes in the sweet spot where the real learning and challenge occurs. The ones where it's uncertain whether or not you'll complete them.

When I'm working on one of these sweet spot problems, I can practice trial and error. I can also talk to other climbers around me and see if they've done it before or pick their brains for ideas.

But the most effective aid for me is simply seeing someone else do it themselves.

Watching a guy or gal make their way up this route that's been giving me trouble...Not only do I get to analyze their hands and feet to learn their strategy. But more importantly, it gives me unquestionable evidence that this pursuit is in fact humanly possible.

On a spiritual level, it almost gives me permission to finish what I started. That's the climbers insight: opening your scope of what's actually possible.

The question goes from Can I do this? to How can I develop the skills and actions needed to make this happen?


My brother teaching me Gen Z language.

Cut to: a session with my coach this past week.

I've been in a complacent spot with my coaching business and income for the last year.

When I was building my practice from scratch, all I wanted to be was "good." So long as my monthly income was higher than my monthly expenses, I was fine.

It took me about nine months to get to that point consistently. And once that happened, I felt immense peace and triumph. I had done it. No more living paycheck to paycheck. I was good.

And it was all from something I had created myself out of thin air. And it came off the back of crippling stress, anxiety, and doubt. I had won the battle.

But after that, I stopped building a coaching business and instead was simply running a coaching business. My fire was gone. I didn't feel hungry anymore. I was good.

What began as a feeling of peace and contentment slowly transformed into a poisonous complacency. The money depleted month after month. I turned my attention to other fun projects like my book and my podcast. I stopped reaching out to people to grow the business.

Until I couldn't take it anymore. I could see myself falling right back into where I was a year and a half ago.

So I reach out to my coach and we began working together again.

I told him I had done the math. All I needed to live my dream life was $9k per month. That would give me all the freedom in the world to spend where I wanted. It would also let me crush my debt on a monthly basis. (My net worth is around -$80k from student loans, a personal loan, and car payments.)

So I explained to him that I really wanted to enter a season of sacrifice and make my financial success my #1 priority.

He called me out.

"Why have you decided it has to be so hard?" he asked.

I thought for a few seconds.

"I don't think it has to be very difficult," I replied. "But I do think there are different habits and ways I could be living that would put me in a much better place financially."

Then he laid into me. Typically, powerful coaching has nothing to do with giving the client solutions and answers. But he has known me for a long time and I asked him before the session to challenge me and tell me his unabashed thoughts.

"I don't buy into this story you're telling yourself, Dillan," he started. "You're one of the most effective coaches and creators in the game right now, and you're thinking the most important thing to figure out is your weekend habits?

"What if you doubled it? You're saying all you need is $9k a month. What if you decided you were going to make $20k a month?"

I smiled and began thinking. He continued.

"Even now I can see you thinking about how. How do I do that? What if you stopped trying to 'figure it out' and you just decided to do it?

"You could be making $50k a month if you genuinely desired that. There's nothing actually stopping you other than your own expectations of what's possible."

Whoa. That's what I tell my clients all the time. It's the biggest truth I've learned from coaching people for years.

We can have whatever we want in this life. The only thing in our way are whatever stories and fears we let keep us from taking certain actions.

Right now, the only thing keeping me from making $50k a month is my own complacency. I've been asking, Can I make $9k? When I should've been asking, What are my next steps to make $50k?

So I did an exercise. I laid out all the constraints, all the things that need to happen. Then I worked backward from there.

Here are the constraints for what I need to create:

  • $50k/mo

  • only working on weekends when I want to

  • no more than 3 coaching sessions in one weekday, 0 on weekends

  • I still have time for creative projects:

  • 1 podcast episode / 2 weeks

  • 2 YouTube clips / week

  • 2 YouTube shorts / week

  • 2 blogs / week

  • 3 days / week writing book

  • time for friends, family, travel, climbing, gym, reading, resting, connecting, silliness, nature, comedy

Now, working backward, how can I get there?

  • charging way more for 1-on-1 coaching and providing zero discounts to new clients

  • going back to reaching out to 10 to 20 people every Monday: connecting, asking people who they know, getting into wealthier and more committed circles

  • publishing my book this summer (not in the hopes to make money, but to free up 5-10 hours each week by not writing it anymore)

  • launching my card game and marketing it through partnerships with other creators with huge audiences

  • coaching company and startup teams for high fees


The point of all this is not about the specific plans and tactics. The point of this article is that our creativity is only as vast as what we decide is possible for ourselves.

When I can't make it up the climbing wall, I've mentally decided it's probably too difficult for me. Then I see my brother do it and I become certain it's doable.

The wall didn't change. Nothing changed besides my own thinking and therefore my own doing.

Insight is when nothing has changed and everything's different. It's when you learn something that was true the whole time. You just couldn't actually see it.

In the next 90 days, I'm going to make $50k in one month.

The only thing that can stop me is my own thinking. Stay tuned.


(Here's a video of me climbing a low-level wall with a heart rate of 128.)


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