You’re 23 and Stuck at Square One, What Do You Do?

Declan Wilson
Photo by Niklas Hamann on Unsplash

Dear 23 year old fresh out of college,

You might think you have everything figured out. You might have landed an interview with a company that promises to utilize your freshly minted diploma. You’re past the agonizing educational period of your life. You even managed to secure your own apartment without the help of your parents.

Everything is going to plan.

And then it doesn’t.

The company you interviewed with never calls back. Student loans start kicking in. And your apartment has this weird smell that wasn’t there before.

You’re 23, stuck at square one, and have no idea what to do next.

There’s no silver bullet, no magical plan, no ailment to your woe — Only hard work and perseverance

If you clicked on this article hoping for a Buzzfeedesque-Oh-I-Totally-Relate-To-This-Situation-LOL-Please-Someone-Tell-Me-What-To-Do! piece, move on. You won’t find it here sister.

Let’s kick things off with a few hard truths:

  1. The past 4 to 5 years of college (and the 13 prior years of schooling) have NOT prepared you for the world as it is today. (Remember cursive writing?)
  2. Your diploma is not a map. It’s not a sacred document or even a recipe for success. It’s a piece of paper. (I don’t even know where mine is, but don’t fret, I have the $500 a month student loan payments to remind me it still exists.)
  3. You aren’t special. You aren’t fulfilling some destiny. You aren’t MEANT to follow a given life path.

Square one is scary. You’ve spent the past 18 years in a structured system that offered clear benchmarks, decent social interactions, and a sense of moving toward something.

That system is now gone. It doesn't exist out in the real world. No one is tallying your test scores. No one is forced to interact with you. No one is holding your hand.

Let me say this again, square one is scary. But it becomes less scary overtime, because here’s another hard truth I didn’t mention:

We’re all at square one.

At 23 I hopped on the first job opportunity that presented itself. I was so scared of square one I shackled myself to the corporate ball and chain, thinking it was the mature and proper next step.

I spent the next 5 years agonizing over how to escape.

The point of being 23 — and your twenties in general — is to not exit square one, but to become comfortable operating within it. Not just comfortable, great at it.

A sad but true story

I worked in a big corporation after college. I won’t name names but they’re known for their ketchup. I’ll leave it at that.

I had this manager. Nice guy. Tenured, in charge of running the transportation department, sat in big important meetings. Was he at square one? No, he was safe of course…

But then our ketchup company was acquired by a bigger company.

They cleaned house.

I was cheap, they kept me.

He lost his job. He had too many vacation days built up.

Fast forward 5 years. I’ve escaped the corporate world, at square one but building my own business and doing okay for myself.

I needed an Uber ride after a meeting.

Guess who picks me up.

My old manager.

Square one was not treating him well.

The moral of the story? Don’t fall for the fallacy that you’ll have everything figured out by 25 so you’ll never have to worry about being at square one ever again.

Like my former manager, square one is always right around the corner, even when you have something good going for you. A job loss, a broken relationship, a death of a friend is enough to derail your sense of security and push you back to the depths of square one.

The point is to know and trust, that even in the worst of scenarios, you can adapt and keep moving forward.

Self-efficacy, that’s the name of the game.

Step One — There is no Step One

Like I mentioned earlier, there is no silver bullet to what you should do next.

I’m not one to give sweeping advice that’s helpful for your specific situation. But I do have a few suggestions on how to start.

Make connections

For the past 18 years you were herded class to class with people in the same age range as you (and probably the same sociopolitical status). In the real world, this is an anomility.

For one, if you want to make connections you have to go out and make them yourself. You have to prove that you are valuable, personable, and

Avoid professional meet-ups when necessary and instead find people a few notches above you with pain points and look to solve those pain points for them. Keep repeating this process and you won’t have to schmooze for opportunities, opportunities will schmooze for you.

Change your mindset

Don’t ask yourself What do I want to do with my life? At 28, you’ll be surprised how much the answer to that questions changes. Instead ask yourself What can I learn or experience today that will yield gains in the future?

I know what you’re thinking, That sounds great, but how does that help me make rent next month? If your main focus is on making rent, you will spend all your energy focused on that short term goal. Once you make rent, you’ll focus on the next month. Before long you’re stuck in a loop.

Books, courses, even traveling need to be treated as investments not sunk costs. Yes, there are basic costs needed to survive (I have a toddler and another kid along the way, I know). Your mindset matters. Actually, a strong mindset is absolutely necessary to survive square one.

When your mindset is focused on short term goals your actions will reflect that. Instead of taking massive action (per Tony Robbins) to push your life in a new direction, you'll settle on what’s easy to do. Every year I try to disrupt my life by doing one big, bold, ambitious thing that is far outside of my comfort zone. Last year I left my full-time corporate job. This year I’m launching a daily vlog and homeschooling my son.

Change your focus to the long term.

Practice in the open

Forget about your resume. Your digital footprint matters more.

If someone is considering you for an opportunity, they might glance at your resume, but chances are they are going to Google your name instead. What will they find?

The easiest way to build a digital footprint is to document your learning experiences with a blog. Even a curated Instagram account will do.

Either way, practicing what you learn out in the open is an opportunity to connect with others in your “field” and helps you build new skills. Eventually, having a well documented and public portfolio will become your greatest asset at square one. (Remember, when you meet people in the real world the first thing on their mind is Who are you and what can you do for me?)

An example: my girlfriend (now wife) and I started a cooking blog while we were in college to document recipes that we learned. Did I become a chef? No. Instead, I learned how to build a website which I had never learned how to do before. I took that skill and built more websites and eventually launched my own business building subscription websites for service-based professionals. I did not predict this path, but it only appeared once I practiced out in the open and acquired new skills.

Some helpful resources I wish I knew existed at 23

I’ll conclude with a non-exhaustive list of resources I’ve found helpful in the years since I was 23. (Feel free to make recommendations in the comment section.)

In no particular order:

  • The James Altucher PodcastJames Altucher interviews a wide variety of people from all fields and careers. I almost listen to his podcast exclusively.
  • YouTube — This seems obvious, but I wish I spent 30 minutes every day as a 23 year old watching a tutorial that taught me something new. Unlike Facebook, YouTube isn’t a vomit stream of useless content, you have a lot more control over what you consume there.
  • Sapiens — Understand the building blocks that makes humans human.
  • Flow: The Psychology of Optimal Experience Find work that gets you in the “flow.”
  • Seth Godin’s blog — Seth is a marketing genius. He’s also an incredibly interesting human whose daily insights always leave me inspired. (You can subscribe to his blog here. Also, check out his book The Dip.)
  • Udemy — Again, courses are an investment. Just be careful about what courses you take. If they promise to make money by taking the course, don’t believe them.
  • Public library — Most library also let you borrow digital books as well.
  • Evernote — Start organizing your thoughts
  • Morning Pages — Tim Ferriss has a terrific write up about the practice here. In summary per Julia Cameron, “Once we get those muddy, maddening, confusing thoughts [nebulous worries, jitters, and preoccupations] on the page, we face our day with clearer eyes.”

Good luck at square one! Maybe one day we’ll cross paths.

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Stay-at-home dad. 9-to-5 escapee. Aldi aficionado.

Baltimore, MD

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