What are you after, anyway?

There's a lot of opportunity for you in the world, given you know what you want.

Cullin McGrath

Nov 4, 2021

Hey friends,

It has been awhile since I have published so I thought I would remind anyone wondering: I write about things somewhere at the intersection of career/entrepreneurial pursuit and lifestyle.

More about me on my website if you’re interested.

I encourage you to unsubscribe if this is no longer your thing <3

What are you after, anyway?

My dad loves to tell this story about me in high-school, deep into my first relationship.

I was contemplating my career, my future, and my relationship. You know, the low stakes, big issues every other sixteen year old faces. Opportunistically, I asked my dad: “How do you know when it’s time to propose to someone?” He gave me some great advice and then read the room, laughed, and said something to the effect of this: “if you need to ask, it’s probably too soon.”

I like to think about this story – partly because my dad finds it so amusing – but also because it was my first real lesson in checking in with myself. I hadn't really had a plan and was just mirroring everything I had seen around me.

Going with the motions had been a recurring theme for quite some time in my life. Including my career. As a textbook generalist, I’ve either worked in or led departments like analytics, operations, marketing, sales, and product. I went where I was needed.

I’ve come to learn something about these experiences. Given you are still moving, many things will just.. simply move along with you. If you work hard and show up consistently you’ll do fine for yourself. But are you doing what you want? Because the world will move you regardless.

It was only until the last few years where I've at least attempted to craft a life I wanted. Because the world will find a perfectly sized hole to jam you in if you let it.

“Either you run the day or the day runs you.” – Jim Rohn

So what are you after, anyway? Is it fame? Is it money? Travel? Challenge? Freedom? Try something with me: Thoughtfully consider what you want out of life. Think about your life ten years from now – think about it all, who you’re with, what you’re doing, where you’ve been, the type of person you are – and write it down. Be honest. Some people want to rule the world, others want to settle down comfortably. There are no wrong answers because it’s what you want.

The next thing you do is this: accept that your reality is as malleable as your plan. When I was younger I thought I would grow up to make video-games. Last year I thought I might try becoming a journalist. This year, I’m dreaming bigger! Learn to experiment devoid of any judgement. Understand that having a plan for the future doesn’t mean it needs to stay the same.

I’m sensitive to the fact that this advice can be boiled down to “have a plan” but the reality is that many of us don’t or didn’t have one. Or we’ve haphazardly thrown ideas around. I’m talking about a living, breathing document that you reference and update often.

I think a lot of people, myself included, get nervous with claiming agency in our lives because we inherently become responsible for the potential fallout. I’ve started and shuttered two online businesses – both profitable, albeit small – due to conflict. I’ve started jobs I quickly realized I hated, invested time in people I shouldn’t have, moved to places worse than before, and only the lord truly knows how poorly I've performed in crypto...

I’m not saying I’m perfect – far from it actually – but I’ve shedded a lot of my aversion around making a plan and seeing what it’s all about. So what are you after, anyway? What you want is probably not that far away. It’s just going to take a lot of work.

Wishing you and yours what you’re after,

Cullin

PS: A few resources I recommend if you’re still looking for inspiration in the world:

Sorry I haven’t wrote in awhile. To be honest, it has been challenging for me. Thanks to many of you who have been an ear for me during writer’s block <3

I’ve been really busy building an awesome community for founders at On Deck Scale. Feeling so very fortunate to get to be doing what I’m doing these days.

By the way – I launched a new website! I’ve realized I never was quite happy with using off-the-shelf website builders. I had this built custom and love it!

Thanks again for sticking around. Here’s some other things I’ve been up to: