Are you making 'tomorrow you' proud?

There are things I’ve always dreamed about doing, but am terrified to actually do.

• Speak in front of large crowds.

• Build a hugely successful business.

• Have kids.

And I’ve developed a theory on why so many of us don’t feel confident enough to go after the things we want.

It’s simple: we stop trying to make ourselves proud.

We say we’re going to do things, we talk about our goals, we fantasize about a different life—but we don’t hold ourselves accountable to making it happen.

If you really break it down, that’s all confidence is! Confidence comes as a result of you proving yourself to yourself—and sadly, most of us give up on that way too soon.

I was about 27 years old when I realized that I wasn’t that stoked about where my life was heading.

Sure, I had a “good” job. I saw my friends often. I exercised. I had my own place. I was a two-time college graduate.
On paper, I had checked off all the “adult” boxes—but the thought of staying on that path felt suffocating. I was boringly busy, but not really fulfilled.

I felt like I’d picked a safe life. And the idea of being on my deathbed, saying that I played it safe, scared the shit out of me.

That’s the mental “click” that changed my mind, and set me on a different path.

What age do you think we dream the most at?

I’d guess 14. When I think back to my 14-year-old self, that’s probably when I had the most romantic view of life.

I was becoming more interested in boys. I was tasting a bit of independence. And this combination had me fantasizing about how cool life would be.
I imagined I’d grow up to be a famous creator, like a painter or a National Geographic photographer.

Picture this: Imagine you’re 14 again.

Visualize the clothes you’d be wearing, what your hair looked like, and where you’d likely be hanging out.

Now, imagine you get to leap ahead in time to 2024 for one hour and see your future self.

What do you think 14-year-old you would think?
Would they be excited?
Would they look at your life and say, “Wow! I can’t wait to become that!”
Or would they think, “...Really?”

I’ll never forget the first time I did this exercise. I was sitting in the living room of my apartment, eating a gigantic bowl of salad.

My heart dropped with disappointment when I realized I had given up on making my dreams a priority. Somewhere along the way, I stopped caring about making myself proud.

That realization woke me up.

I always say that my best writing happens when I’m speaking to my younger self. I’m always thinking about what advice I’d give her and what I’d want her to know.

But this exercise flipped the question: What would she think of me?

I’ve spoken to over 727 people who dream of leaving their jobs to build their own business. But fear keeps them from taking action. Some of them, now in their 60s and 70s, have spent decades dreaming without ever starting.

That’s why I’m writing this. We assume it’s safer to keep doing what we’ve always done—but that comes at a cost.

I recently heard one of my favorite speakers, Chris Williamson, explain this perfectly when he quoted the best piece of advice he’s ever received.

It feels scary as hell to change, but making these changes really isn’t that hard—you just have to tweak how you think about it.

I’m scared all the time that what I’m working on won’t be successful. But I don’t let that fear stop me.

I just keep asking myself: “Would ‘tomorrow me’ be proud of this decision?”

This is how I started caring more about what I think of me, and less about what other people think—and it really has changed my outlook on life.

The person you are best-equipped to help is your old self.

I don’t have the answers for how to make all of your dreams come true. I’m still working on that myself.

But I believe that the person I am today would make my younger self proud, because I’m back to being a dreamer.

I’m not willing to settle anymore for crappy relationships, or jobs that I don’t want to do.

I don’t know how long it’ll take me to make my daydreams happen, but I know that trying to make myself proud every single day is a simple way to help me get there.

Never give up on yourself.
Maybe that’s the big takeaway here!

If you’re committed to
working for yourself
AND progressing in fitness,
we’ve just launched our inspired idiots community
to help people like you
network and figure out
exactly how to actually make that happen.