Five Things I Could Have Done Better in My 20's

On September 1, I’ll turn 30 years old, and… it’s been a weird summer. I always promised myself I wouldn’t be one of these people that wouldn’t be overly sentimental about milestone birthdays like this, and while I truly have no problem getting older, I’ve had a very “retrospective” kind of summer.

Maybe I’m being naive, but I can’t imagine how my 30’s will be as wild of a ride as my 20’s were. Not that I actually did anything all that wild (I’ve led a very boring life), but I’m a totally different person today than I was ten years ago. I began this decade in undergrad, eating way too much pizza and playing way too many video games. Since then, I’ve started my career, lost 100 pounds, got married, and had two baby girls. Talk about change!

Anyway, with this retrospective time, I’ve assembled some stuff I’m glad that I did and stuff that I wish I would have done a little better. We’ll start off in this post covering the stuff I wish I would have done better and return next week with the things I’m glad I did in my 20's.

Let’s get into it!

1. Investing. Period.

With the launch of the second edition of I Will Teach You To Be Rich by Ramit Sethi, I’ve been thinking a lot about my family’s financial future. While I’m glad my wife and I did certain things (which I’ll cover in next week’s post), I’m kicking myself for not getting the ball rolling on investing sooner. I’m not even talking about getting into the stock market necessarily; I’m talking straight up putting money into mutual funds or even CDs. And I can summarize my concerns with a single term: **interest rates**. The math Ramit lays out in his book is so simple and explains so easily why anybody should start investing as young as possible. All is not lost if I start now, but if I’d have started ten years ago… we’d be in a much better place in the long term. *sad face*

2. Building a portfolio of work.

Okay, I’m cheating a little here because I have done this better in the last year or so, but I still wish I would have started much sooner. The olden days of submitting a resume for a job and displaying your skills on paper are quickly passing away in this world where technology has enabled us to share tangible demonstrations of our work. Whether it be a blog or a GitHub repository, being able to demonstrate your work speaks FAR more than a simple resume could ever do. When I was first looking to enter the workforce in 2012, I struggled big time to land a position because of my naivety in thinking that my resume would speak for itself. Had I known what I know now, I’d definitely tell a 20 year old me to get on top of this ASAP.

3. Balancing soft skills with hard skills.

Both my undergraduate and graduate degrees are in soft skilled leadership / business areas, and I’ll be honest… neither of those degrees have done much for me at all. I’m not at all disparaging soft skills, but the fact that I spent so much time and thousands of tuition dollars in learning soft skills while ignoring hard skills was a huge mistake. It wasn’t until a mentor of sorts came my way and pointed this out in my late 20’s did I start to course correct here. Again, had I taken these things into account when I was still a young pup in undergrad, I might not have had such a difficult time getting my career off the ground.

4. Worrying about what other people think.

I know, I know, this one is a bit of a cliche, but it’s far truer than I think we realize. I see people even late in their careers doing everything they can to climb higher in their positions at the sacrifice of, well, basic living. I’m not saying there’s not a time and place for putting your career first, but when it gets to the point that you’re breaking your back trying to get into a position you’re not really wild about anyway? It’s just not worth it, friends. And while I use the analogy of moving forward in your career here, I don’t mean to limit it to just that. Whether it be trying to impress your parents or win approval from your friends, the reality is that the grass isn’t as green as you think it might be on the other side. In the words of Ram Dass, be here now. Stop chasing after an uncertain tomorrow.

5. Enjoying life in general.

It might not seem like it through these blog posts, but I have a strong tendency toward anxiety and pessimism. I’ve come a long way in the last year or so, but much of my 20’s was spent worrying about the future so much that I didn’t stop to smell the roses. My wife and I were so fixated on our careers that we only took 2 vacations, and even then, the second vacation was limited to just 3 business days. In retrospect… I truly don’t know why I worried so much. Even if the worst case scenario situations would have come true, they wouldn’t have been the end of the world. Again, there is definitely a time and place for focusing on your career, but if it becomes the only thing you do, you risk ending up a shell of the person you truly hope to be.

That wraps up this post! Thinking back on your 20’s, what might you add to this list? I’m curious to hear how my millennial perspective might be different from those folks in different generations. Next week, we’ll come back to take a brighter look at things I think I did well in my 20’s. Catch you then!