A cautionary tale on going after your dreams

What happens if you don’t change? A cautionary tale.

About five years ago, when I started Milk the Pigeon, I had joined multiple masterminds.

I was extremely hungry, extremely unhappy, and extremely ready for a change.

A big one.

So I would seek out some people, do a bit of digging, see what they were up to, and then ask them to join the mastermind.

In one particular mastermind, there was a guy that (from the outside) seemed like he was the same as me.

He seemed ambitious.

He seemed like he dreamed big.

He seemed like he was going to make things happen.

We both talked about having that massive vision for the future, about going to all these spots once we had quit our jobs, doing whatever the hell we wanted, and so on.

But within a month or two I realized there was a huge difference between us.

Whereas I’d get advice, and implement it the same week, he wouldn’t.

He would always be overthinking and second guessing himself:

  • Yeah this business sounds cool but…
  • Well, I could go down this path, but what if i’m missing something more important?
  • I mean… MAYBE I’ll take this day job temporarily and see what happens.

The big difference was that he was caught in thinking and took almost no action.

Three months in – 100 days – we did a checkin.

Alex: Started a business, then ditched it, realizing I didn’t want to do this particular one. Then started another and committed.

Other guy: Exactly zero to show in the real world about what he had built. He went on some long winded explanation about his doubts, concerns, fears… but at the end of the day, had nothing to show for it.

And the most haunting part?

Five years later.

Here’s what those two paths look like.

Five Years Later

Other guy:

– Still stuck in a job (got fired, then got a new one)

– Still “having all these business ideas”

– Still wants a business

– Still virtually lives in the same area and does the same thing every day


Despite being confused as all goddamn hell and making most of the mistakes, I just forced myself to act.

And as a result, here’s what happened to me five years later:

– Have a book, with a second one coming out soon (And the royalties almost pay for my rent alone)

– Have a modestly successful online business (And quit my job)

– Have traveled to two new countries every year

– Finally “found” and have the time/luxury of money to go after my biggest passion/calling.


This is NOT to compare us – but just to illustrate a powerful difference.

One is the result of overthinking and not taking enough action.

One is the result of both thinking and applying tiny actions each and every day.

BOTH of us had no goddamn clue how to reach our goals – that’s important to remember.

BOTH of us had the same inborn genetic potential to go do something, or big things.

But it ultimately came down to who did the work, who took the imperfect action, who thought – but then DID — that mattered.


Where do you want to be in five years?

A little cautionary tale.

It was not an exaggeration to suggest that I would’ve killed to understand all these principles years ago, to kill my inner perfectionist and just act.

Which path do you see yourself going down now?

2 comments / Add your comment below

  1. I agree. The only way to get stuff done is to act. Don’t think, just act. Overthinking kills everything. I thought myself out of happiness, out of certain opportunities… it’s such a destructive pattern.

    1. Hi Cristian! Thanks for your comment. I agree with you, having been an overthinker for most of my life (and still trying to kick that habit), I can attest to how that pattern can be really destructive. I personally procrastinated alot, and became so risk-averse that I missed out/delayed a lot of opportunities. Never again!

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