2 Harsh Business Truths I Learned the Hard Way

Dillan Taylor
6 min readJun 12, 2024

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So you don’t have to do the same.

When I became a certified life coach.

When I was 26, I…

  • stopped waiting tables
  • started doing door-to-door sales
  • quit that job to run my own business

I’ve been a full-time life coach and creator ever since. Here are two business lessons that sucked to learn.

1) No one’s coming. 🔮

I wanted to be an actor growing up.

I memorized dialogue from my favorite shows and movies, acted out hypothetical Late Night interviews, and even wrote an Oscar acceptance speech.

But I never pursued it. I never took even one step toward getting on stage or behind a camera.

Until senior year of college.

My theatre friend told me about an audition for that semester’s play: To Kill a Mockingbird. I imagined myself in overalls and makeup.

But on the day of the audition, I convinced myself not to go. Why?

  • “I have no experience.”
  • “The theatre students all know each other; I’m an outsider.”
  • “I’ll just embarrass myself.”

Or so I told myself.

Then it hit me.

I wanted to be an actor. I wanted the result of acting on stage and being good at it.

But what was I expecting?

Was the director of the play going to drive to my house, knock on my door, and tell me, “Hey! We’ve never met. But I’ve seen you walking around the theatre hall. You strike me as someone who can act. Do you want to be in my play?”

No.

The only option to even have a shot was to get my ass to the theatre, grab a script, and audition.

The same is true for any pursuit: a business, a podcast, a blog, etc.

# of ideas I’ve had or heard = 4,873
# of ideas I’ve seen executed all the way through = 4

That’s a real statistic I made up.

Lots of people I coach get pissed that everyone else is succeeding besides them. But that couldn’t be further from the truth.

Because most folks aren’t even playing the game. Most people don’t audition for the play and are upset because they can’t be actors.

I’ve seen so many coaches get frustrated by their lack of clients. Meanwhile, they…

  • don’t reach out to people consistently
  • don’t gift sessions
  • don’t ask their friends for referrals

I’ve also seen countless entrepreneurs and creators believe that if they build it, people will come.

Not true. No one’s coming. So it’s up to you as the builder to build it loud and build it well.

When I started Grindstone, I told my business partner: “We’ll just do cold outreach, then set up sales calls, then start getting paid clients.”

Little did I know that meant I had to do cold outreach, set up sales calls, and start getting paid clients.

When people hear what I do, they often tell me their ideas for a podcast, blog, or YouTube channel. It fires me up every time. But it’s also taught me something important.

Every idea is good. 💡

Because an idea is just a few spoken words. It’s fun and easy.

What’s less fun and easy:

  • taking risk
  • working hard for no results
  • uncertainty
  • doing tedious and boring work
  • marketing
  • potentially failing
  • investing time, money, and energy
  • getting brutally honest feedback
  • sucking at something

But that’s where the results are.

Reminding myself that no one is coming has saved me tons of heartbreak.

Putting in 100 hours to make something work isn’t painful. What’s painful is expecting something to work after putting in 10 hours. It’s made me burn out, give up, and doubt myself.

No one’s coming to hand you the job you want, your dream client, or success. So go get them yourself.

2) There are only 2 reasons you’re not getting the results you want. 📊

  1. You’re not good enough yet.
  2. You’re working on the wrong stuff.

Let me explain.

Club de ajedrez, Medellin Colombia.

I started playing chess because I wanted to beat my competitive friend. Each loss to him felt like a knife in my gut.

Why did he win most of our games?

It’s not because…

  • he was an asshole
  • I was tired
  • I had the wrong goals

It’s because he was better than me. So I had to improve.

But how?

I played tons of games against the computer to try to get the hang of things, which is an inefficient and sluggish way to improve.

The computer plays like a computer, not like a human. So familiarizing myself with that type of play didn’t actually prepare me for my friend.

I worked on the wrong stuff.

I only started making noticeable progress once I looked at my actual games with my buddy and analyzed them. I…

  • found my most common mistakes
  • sharpened my opening repertoire
  • solved puzzles based on my biggest weaknesses

Lo and behold…I began winning more games.

I’ve done this in business. I’m doing it right now lol.

We started a community for Grindstone — accountability coaching for creators. The goal was to build a hub that would attract future coaching clients.

But in growing it, I got hyper-focused on the community: the group calls, the awards for games, and a potential course for members.

That’s all lovely. But the whole point of this was to build a profitable business based on my expertise: coaching. Having a thriving community is certainly a useful long-term strategy for sustaining that business. But in the meantime, it does nothing to make money.

I asked myself a few questions last week:

  1. What has made Grindstone money so far?
  2. What beliefs do I have that are holding us back?
  3. What’s stopping us from making $5k/month?

My takeaway:

I’m actively choosing not to do the thing that makes Grindstone money—gifting people coaching sessions, setting up a sales call with them, and signing them up for paid coaching.

If the goal was just to grow the community to 1,000 members then our current system is fine. But we want money like the corrupt and scummy capitalists that we are. 💰

I’ve been working stressfully hard on the wrong stuff.

Alex Hormozi says there are only two ways to make more money in business:

  1. get more customers
  2. make your customers worth more

Anything that doesn’t do one or both of those…is probably not worth your time as a business owner (aside from obvious tasks like taxes, etc).

A high-quality video course for creators will be insanely useful. But right now we just need more customers.

So I started doing regular outreach again to set up gifted sessions. I asked my friends who they knew who could use more accountability.

Shockingly, I have gifted sessions on my calendar now. We have people in the funnel.

It’s tough to admit that you’ve been wasting your time in some way. It can also be helpful to waste time so you can learn what actually is important.

But once you identify the regular actions you take that aren’t moving the needle, you can replace them with ones that do.

If you’ve been doing the same thing (creating the same YouTube videos, providing the same service, living the same life) and you don’t have the results you want…you need to work on different things.

If you want to follow my journey in growing Grindstone, get lessons from top 1% creators, and join me as I travel the world with my laptop…

Find me on:

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Dillan Taylor

Helping creators do their work, make better content, and grow an audience.