The Cost of Betting On Yourself

One of the hardest things in life is becoming completely comfortable with your unique goals and your way to get them.

Ryan Holiday, one of my biggest idols, said

“Doing something truly great means suffering a bit for it. Being misunderstood. Taking longer. Risking more.”

This has been massively prominent in my life recently.

This is the first summer where I haven’t gotten a typical job. I’m not serving or bussing tables or even rock climbing coaching anymore. My jobs are growing this podcast/ personal brand and developing a climbing clothing brand called Open Project.

I will most likely make much less money than I would want to this summer. I will still make some, but not a comfy amount.

At 18, that’s fine. I made an incredible amount of money in scholarships for school next year, which I am so grateful for, and that also helps afford me this opportunity.

Here’s the truth I keep reminding myself of: this financial discomfort, and the social discomfort of doing something different, they are just the costs of choosing the long game. I am betting on myself, building something that doesn’t pay me like a pay check right now— but one day, it could pay me in freedom, fulfillment, and joy in a way that no hourly job ever could.

It is incredibly easy to fall into a jealousy or an isolation trap.

In last Wednesday’s episode, my guest, Lachie Colledge, reminded me of that I would never trade experiences with another person in this world, because I love my life more than anything. Therefore, I cannot be jealous, nor pity myself. This perspective lets me be happy for others and supportive of them in their decisions because I know that I wouldn’t trade my life for theirs, no matter how awesome it is.

This perspective shift has been massive for me.

I no longer feel the need to conform to other people’s expectations or change my behavior based on their opinions. I honestly feel myself starting not to give a f*ck.

I realize now that I am allowed to completely and fully love what I do, even if others think I am a complete psychopath for doing so. For all I know, maybe I am a complete psychopath for working 12 + hour days in the summertime. Who else does that?

When I introspect, though, I feel so delighted by this. I know that what I am doing is exactly what I want to be doing. When I land back in this, and I prioritize some introspection or quiet time, I end up much clearer on my purpose and my mission.

This realization has also changed the way I work a lot, and I think could provide a lot of value to people out there struggling to work long periods of time without stopping.

Build in fun and nature into your work day.

Not having school and sports every day means that when I am not working, I am free to do whatever I want to do.

For me that has meant more rock climbing, more hiking, more surfing, more time with family, more time with friends. It means slower meals, more meditation. It means more choice.

None of what I listed there was “productive” in a work sense, but all of it makes me more productive.

I have realized that in order for me to work my most efficiently, I must have already exercised or know that I will be able to exercise soon. Additionally, I need non work related conversations with friends and family to keep my work psych high. Nature also helps.

For many of you, these pillars of a good, productive, fulfilling work day may be different, but I guarantee that you have them.

When you test things out enough and slow down to figure out what feels right, prioritize those things. You are getting this advice from someone who has spent the entire past 14 months trying to convince himself of the same thing. Don’t go through the pain I did: prioritize yourself over your work because your work is reliant on yourself.

So, if you’re in a season of uncertainty, discomfort, or just trying something new, remember that you weren’t meant to live a life that looks good to everyone else but feels wrong to you.

Figure out what your fuel is and embrace it. Protect it. Be proud of it. Prioritize it and everything that helps it.

Whatever you do— don’t wait for permission to go all in on what you love.

You’re not here to copy anyone else’s version of success. You’re here to live yours.

BIG STEPS:

I’m on a mission to hit 100,000 podcast downloads before I head to Northeastern at the end of August.

No big team. No crazy studio. Just deep conversations, a mic, and a vision I’m obsessed with.

If this newsletter resonated with you, the best way you can support is to listen to an episode, share one with a friend, or leave a review. It means the world—and helps this thing grow more than you know.

The Grateful Podcast:

I have a podcast where I interview people much smarter and more qualified than me talking about how you can live a more purposeful life full of gratitude and ambition. 
I release episodes every Monday where I go over a lesson I’ve recently learned.

Every Wednesday and Saturday I release an episode with a very cool guest. 

You can subscribe on Apple Podcasts or Spotify, or find the video version on YouTube.

This week’s episodes:

Monday: The Cost of Betting on Yourself

I will dive into my thought process writing this newsletter and more personal examples.

Wednesday: Joshua Dean Church

Saturday: Jess Prudhomme

Coaching:

If you’re ready to take action and need guidance, I’d love to help.

I have limited space available so if you’re interested, book a free 15-minute call with me to discuss your dreams and how to start making them happen. 

You can shoot me an email at [email protected] where we can get scheduled.

Make this week rock. Thank you so much for reading this; I’ll see you next week.

Gratefully,

Jack Wagoner