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A Decade of Reflection – Greatest Learnings from My 20s

We’ve already written an article about Things to Avoid in Your 20s, so I thought it would be fun to focus on some of the more positive takeaways of my 20s. Being on the early end of my next decade, I’ve had about a year to think through what my 20s meant to me. Stressful, frightening, challenging, exciting, and fun are all great words to describe that time of my life. However, even when you take that jumbled bag of emotions and sum it up, it was AWESOME!

My 20s saw me graduate undergrad, take-in my pup Jet, go to grad school, navigate romantic relationships, move 10 times, start a career and travel the world. There were many learnings from my 20s and I hope you can relate to my top 5.

Here are the greatest learning from my 20s 

Go Big or Go Home

This is the time in your life to dream BIG! As you look at your early 20s, most people have graduated from college or been in the workforce for a couple of years, both of which are huge accomplishments. Now isn’t the time for complacency though. Figure out what you want to do with your life and then determine how to make that a reality. It’s okay if you’re approaching 30 and still have no idea what you want to do with your life, that is common. A career does not exist in a straight line trajectory and is instead, comprised of many turns, mistakes, failures, and successes. Your 20s is your chance to take a calculated gamble on your career and gain new, valuable experiences. Even if experiences don’t feel valuable, EVERYTHING you do carries a lesson that can be applied to your job. 

This point was proven when I worked in property management at 21 and was trying to go to grad school to learn more about the sports industry. Other than some high school football coaching, I had no relevant sports business experience and should have felt unqualified during an intensive two-day grad school interview. Instead, I realized that my experiences with finances, contracting, real estate, management, and customer service, were all valuable skillsets that apply to all jobs and actually made my experience unique compared to my competing applicants. Despite limited sports industry experience, I was able to lean on my business experience and apply it to the grad school curriculum to successfully earn my place in the program. Little did I know that being a property manager would lead to my dream job in the sports industry, albeit in a very roundabout way. 

Ohio University graduate school classmates, class of 2014
OU MSA Class 2014

Be Adventurous

I love to travel and learn about new cultures. I was fortunate to have the chance to travel to Europe, Israel, Hong Kong, South America and throughout the U.S. during my 20s. Some for work, some for pleasure, but all amazing experiences. I always tried to open myself up to new experiences during my travels, realizing I may not have the opportunity later in life where no one is dependent on me and I can afford to take risks. 

It doesn’t have to be travel. During your 20s, challenge yourself to go outside your comfort zone, try new things and expand your horizons. This can be taking on a new hobby, joining a new social group or checking out a music festival. 

For any work trips I went on, especially the ones that were abroad, I always tried to tack on time at the end of the trips to explore the local culture. None more was this true than when I worked the 2016 Summer Olympic Games down in Brazil. Having met so many interesting locals through our month-long Olympic program, I was fortunate to have a network of newly acquired Brazilian friends willing to share their local culture with us. We tried new foods, enjoyed their beaches, explored historical sites and got to feel slightly ingrained in their daily lives. These types of experiences are not only great memories but have helped shape the person I am today. 

Slightly Educational - 2016 Rio Olympic Games
2016 Rio Olympic Games

Develop a Personal Awareness

I dated on and off throughout my 20s. A romantic relationship can be both gratifying and comforting and carries great value in most people’s lives. Relationships also require compromise, and often in your 20s, this is directly correlated to drama. I am not a fan of drama and was fortunate to have dated some amazing women relatively drama-free. While most of my relationships in my twenties eventually came to an end, they taught me how to better communicate as well as realize the qualities I most value in a partner. Thanks to these learnings, when my now fiance came along, I knew she was an ideal fit and a catch. 

With all that said, relationships with others are important to develop a lot of interpersonal skills, but even more valuable is having a healthy relationship with yourself. I don’t believe someone ever stops learning, growing or evolving, so setting a strong foundation for personal reflection in your 20s is crucial. Lacking confidence in your own skin or feeling as if you’re living a fraudulent life is a common perception in your 20s. Constantly being judged by your boss, dating apps, friend groups, etc, creates a consistent sense of lacking self-worth. That is why it is so important to spend your 20s determining what type of person you want to be and what values you are going to live your life by. I went through long periods where I did not actively date and this enabled me to focus on how I could better myself. Eventually, coming to peace with the person I am and sticking to my values inherently led to things such as a great job or my ideal life partner. 

A helpful exercise is to take the time to reflect and write down your top 5 core values you want to live life by. Approach every day with the intent of staying true to those core values. 

Slightly Educational - Relationship Goals

Avoid Debt at All Costs

This is something I failed at miserably! I spent too much on social activities, took student loans for my education and personal loans out for business ventures, and lived slightly outside my means given my salary. I very much lived paycheck to paycheck throughout my 20s and was never able to take a long-term approach to savings. 

Anyone ever challenged by debt can relate to some of my struggles. The challenge with debt is that once you get behind, it is hard to get out of debt sort of like a financial quicksand. Credit cards make the majority of their money by charging high-interest rates on unpaid monthly balances, phone service providers will turn off your phone line and then charge disproportionately high rates to turn them back on, and student loans appreciate your interest during forbearance. I don’t wish these scenarios on anyone, and yet, this was all too common during my 20s. 

Now, wait! I know I said this lesson was to discuss the positive sides of my 20s, so why all doom and gloom? Well, it would be disingenuous to leave out my struggles with debt as a summary of my 20s, but there is a positive side. As my income increased and I improved my financial literacy in my late 20s, I managed to pay off nearly $15K in credit card debt and increase my retirement savings contributions. If I could go back to 21-year-old Matt and tell him the importance of being frugal and financial sound, I would. However, as I mentioned early, your 20s are about making mistakes and hopefully learning from them. I am now more informed and better equipped to make sound financial decisions as I enter the next stage in my life.  

Friends Are Precious

I saved the most important for last. If you haven’t gathered yet, your 20s are messy, challenging and a blast. This is why having good friends are so important. Those that are there for you when you mess up, throw back some beers for your successes and challenge you to go outside your comfort zone. 

If there is one thing I am most proud of in my life, it is that I have surrounded myself with excellent people. Friends that will always be there for me and help me regardless of the situation. The best part is that these friendships are two-way streets, and I would do the same for them. 

In my early 20s, my parents went through a divorce that was hard on me, whether I wanted to admit it or not. At the time, I definitely tried to live life by the “Man Up” mantra and wasn’t great at communicating my emotions externally. Because of this, I didn’t tell my friends about the divorce for a while, depriving me of the support I desperately needed at that time. Once my friends got word of what was going on in my life, they rallied behind me immediately, providing the support and compassion I was craving. This taught me two critical skills: 1) it’s okay to rely on others and in fact, it makes me stronger; and 2) communicating your emotions is a powerful tool to connect with others and actually reflects a deeper grasp on interpersonal skills.   

Slightly Educational - Great Friends

By surrounding myself with positive, ambitious and caring people, I myself am driven to be better. Their promotions at work drive me to elevate my performance at work, their weddings make me want to find someone who I can share that experience with (fortunately, I have), and their ability to overcome challenges gives me strength. Whether you have one or many friends, just know they are precious and do everything in your power to cultivate those relationships. 

In Summary

Everyone has a different life story, but I imagine a lot of what I’ve shared is relatable. If there is one thing you take away from this article, it should be that your 20s are going to be messy. But you have the strength, acumen and support system to grow from your experiences and set yourself up for success in your 30s and beyond. Approach every day with intent and you will consistently continue to better yourself. 

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