The stakes in making leaps

Why you may need to find comfort in discomfort.

Hey everyone,

I hope you had a great weekend with friends and/or loved ones. And as always, thank you for reading. It means the world to me.

Quote of the week:
“Life moves pretty fast. If you don't stop and look around once in a while, you could miss it.”— Ferris Bueller’s Day Off


Sometimes, I like to imagine a dubious, quick-witted genie granting me a myriad of wishes after rubbing an antique-store lamp. The possibilities that would present!

The things I dream to change about myself and the world around me.

Do you know what you would wish for? Would you change your career? Would you change your life? Would you have an unlimited amount of money, or perhaps finally be able to pursue your wildest dreams? If you’re lucky, you may not change a damn thing.

However, most people want to change something in their life. Whether it be their career, relationships, family, location, health, confidence, or even their abilities. If we’re both being honest with one another, the Hollywood dream of a genie making grandiose change is a pointless facade. A useless exercise in imagination.

We’re not granted three wishes, we’re granted three options. We can slowly tool ourselves for the life we want, accept some level of complacency, or make a leap.

A big mistake that many make is thinking that change is a dish best served in time. That instead of fixing it now, you could fix it later. I find this to be a rather tragic perspective on life because it carries the underlying assumption that life is infinite. This is why the genie facade is so appealing. You blink and things are exactly as they should be. There is no pain endured, no effort expended, no can to kick down the road.

The idea of making leaps is deeply personal and relative to yourself. For some, a leap might just be putting aside your deepest fears and finally asking out your crush. For others, it might be throwing your hands up in your career and trying something new. For all, it can be terrifying and feels akin to facing a scary monster under your bed.

A leap is when you invariably decide that something isn’t quite right and the best route forward is pole vaulting forward into the unknown. It’s when you actualize the latin phrase Memento mori, come to terms with your mortality, and just go for it.

I’ve always been critical of my ability to converse. I like to think I can hold my own, but when I have to carry a substantive conversation with someone new I sometimes panic. The thing with making a leap is that it requires you to truly rectify your current positioning with what you want out of the world. And so I gave Toastmasters a try. It was a fairly small leap, but I was pretty nervous about it all. The lukewarm coffee and grocery store pastries the event provided could never provide much solace in that.

After talking it up in my head for so long, it was pretty demoralizing to find out that it was a waste of time. I leapt and missed, which I would soon find is pretty easy to do.

There was also the time that my relationship with my first love completely disintegrated in front of my eyes. That in itself wasn’t a leap, but after absorbing her share of the rent and living off of ramen noodles and Little Caesars pizza for entirely too long, I leapt big and bought a house. I made that bet and scraped together what was quite literally everything left of my savings and raised the stakes even more.

I slept on the basement floor of that house not too long after closing and optimistically thought that maybe now I had leapt and done it. I would rent two of the bedrooms to my friends and I’d start building my life. I’d focus on evolving my career, dabble in real estate, and perhaps find my footing in the world.

An ineffective inspection would blow up in my face. As luck would have it, just about every major appliance would soon die. The heightened ownership evolved what was once an easy ticket to maintenance into massive loans with serious implications on an entry level analyst salary. Among a myriad of emergent interpersonal issues, I spent many nights laying awake at night wondering why I had even leapt at all.

I could drag this on in perpetuity, but I do want to share one other scenario. I left a comfortable, high status role for one with a substantial increase in pay, challenge, and responsibility. It was perhaps the first time that I had seriously paused and considered the implications of doing so. And soon after opting to leap, my fears were realized. The job laid me off 5 months later when sales weren’t so great. Now, I carried what I felt to be a black mark on my beautiful resume. I slipped into the depressive stage of unemployment, interviewed relentlessly, and tried to compute how I ended up there.

I took a job across the country. I’ve moved too much, but it was the first time on my own and without much semblance of a community. Let alone any savings. I welcomed the leap because I wasn’t blossoming in Michigan and felt held back.

I was fearless at first. I sold or donated most of my belongings, left loved ones in the literal rearview, and brought what could fit in my car with me. As the story would have it – and after days of driving – that first night may have been the worst of all. I was drastically oversold on my sight-unseen apartment and had to slug all my shit up 5 floors by myself. I didn’t have a bed, food, or even anyone to even complain to.

It stormed that night while I raced to beat out department store hours. I way over-extended on my credit cards. I remember sitting in the parking lot of Lowes when my dad called. Everything’s fine here, dad.

But everything wasn’t fine, I leapt and everything was fucked yet again!

Through all these leaps and many others, I’ve learned a few critical things. We’re often apprehensive of taking leaps because of the fallout that we might experience. And the more that you decide to leap, the more these risks make themselves abundantly obvious. We’re scared to leap out of fear of making the wrong decision, judgment from our peers, and an innate desire to retain as much control as humanly possible.

And so many don’t end up leaping at all. Even after staring down fallout time and time again, that still feels like an even bigger risk to me. I’m still not the most confident speaker, but I think many would argue I’ve gotten better. I’m also in the process of selling that house and stand to make pretty good money on it. Also, that job I moved across the country for? It turned out to be a bad fit for me and so even now I’m a week out from starting somewhere great. Most things work themselves out.

I don’t say all of this to depress you. I’m stronger for these experiences. However, we read stories about people that make leaps and I’ve never felt like they paint a true picture. They’re always romantic and celebratory. Elon Musk rolled all of his proceeds from selling PayPal into building three different companies and could barely make rent. Many put these scenarios on a massive pedestal. What courage he had. A fearless visionary! But few recognize the pain he likely endured along the way.

And I know damn well that even Elon laid awake in bed at night - perhaps not too different from me. Wondering if he too, had fucked up yet again.

When I originally drafted this piece I was going to talk about everything that leaping had done for me. It has led me to make and strengthen beautiful friendships, build businesses, and experience an entirely new ecosystem. My worldview is forever changed and I’m absolutely better for it.

Sometimes, I wonder if a leap is just mathematical in nature. Is the pain great enough to suffer the fallout from change? When looking at others, it’s easy to judge their toxic careers, life positioning, or torn up relationships. But every one of us has been in one of those scenarios, crunched the numbers, and put up with it for longer.

I’ve also made a major assumption up until now. Even though I’ve faced hardship, I’m not sure any of it would have ever been entirely fatal. Many have been dealt a more challenging hand and sometimes making a leap outright isn’t feasible. Sometimes, the best route forward is culminating marginal change through the years. And like I said earlier, your leaps will only ever be intimately personal to your circumstances and I whole-heartedly commend you for pushing forward against all odds.

I was originally planning on sharing more functional advice on how to make leaps. It was going to be fluffy and full of quasi-academic encouragement. Through writing this, I’ve come to realize that doing so would rob you of the experience you need to make the necessary change in your life. I’m a better professional because I thrust myself into those positions, I’m a better friend because I put myself out there, and I’m better because I tried more of the world on for size.

You know what you need to do so just get on with it already. There’s a monster rolling around under your bed and you can’t always call on someone to save you from it.

There are stakes. You might get swallowed alive. But don’t ever let that stop you from actualizing your dreams.

Only you can peel back the covers, throw caution to the wind, and face it yourself.


Recent Photos

Every once and awhile, I like to share some casual captures. I hope you enjoy them:


Wishing you and yours the absolute best,

Cullin

(Intro photo by Mick Haupt on Unsplash)