When You Should Bet On Yourself

Heceta Head Lighthouse by John Fowler via Flickr via Creative Commons License 2.0.

An interesting conundrum I struggle with at times is when is it time to invest in and bet on yourself.

You don’t want to waste your time and money but at the same time you sometimes really need to dive into an endeavor in order to give yourself the best chance for success, right? So how can a person tell the difference between when to not bother, when to skate by with the bare minimum, and when to go all out?

I’ve lost count of the times I’ve made investments of time and money and they haven’t panned out. I’m sure you have too. Like buying a bunch of art supplies for a painting class (and I still cannot paint for shit), spending a few thousand bucks on a work certification I never, ever used (But maybe someday? No, probably not… haha), and various musical instruments throughout the years (I still can’t play anything other than the recorder they made me play on in first grade).

But I can name a few times that I’ve made the investment, and it turned out to be worth it.

So I’ve been thinking about it, and the common thread is this:

It’s worth it if the money is a symbol of your deep emotional commitment to your project. It won’t work if you think the investment will spawn deep commitment (See the business model of every gym ever that banks on a majority of their members never showing up.) – the commitment must come first. But if you’ve already staked your reputation, life, and/or emotional energy onto something that you really value and find incredibly important, then I will argue that there are few better ways to spend your money.

Because then you’re investing in a dream. Your dream. Something that makes you excited. Something that makes you get up in the morning. Something that makes you happy when you think about having the end goal. When’s the last time you spent money on something that had that much power for you?

And if you had a dream that meant that much to you, and made you feel something that strongly, will you regret spending money on your dream, even if in the end you’ve failed?

I feel confident in saying no. You won’t.

I committed to hiring a personal trainer when I weighed 200 pounds, and stuck with her even when I wasn’t really having much success somewhat early on. Because I was committed to the process. That was worth it.

I committed to running the Bolder Boulder in 2015 and 2017 by buying my entrance fees early on. So on those days that I didn’t necessarily feel like running…. I went anyway. Because God forbid I get bad race results plastered all over the internet for years to come because I skipped a few training runs! And you know what… both of those years, I stayed on track with my plans. I ran through flash floods up to my knees, late at night on the roads and on treadmills (a special kind of hell), through colds and flus and 102 degree fevers, in neighborhoods blanketed with ice, in blizzards, and in 90 degree heat, all because I had a dream to run that stupid, stupid race, in a certain amount of time.

I committed to retiring early by selling my Toyota Prius and living a car free life.

Aaaaand I upgraded my (cheap, horrible) web hosting from webhostingpad.com to bluehost.com this past weekend. Because I’m deeply committed to making this space a something. What exactly, I don’t know yet… it’s a journey for me that I’m still stumbling my way through, but it’s going to be a something.

When has it been worth it for you to dive in?

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