I recently hit a milestone – my late twenties.
Most will say late 20s start at 27, but this was my first full year out of school since I started preschool, so I call it at 28.
It’s not quite 30, but it’s definitely far enough into my twenties to have gained some perspective.
As I look back on the past eight years, I’m struck by how much I’ve learned, how much I’ve changed, and how many misconceptions I had when I first entered this decade of life.
My twenties have been a rollercoaster ride of experiences – some exhilarating, some terrifying, and some that were a bit of both.
I’ve had incredible highs, like starting my own dream business and falling in love.
I’ve also faced crushing lows, including breakups, the deaths of close friends, and the realization that my “dream job” wasn’t all it was cracked up to be.
Through it all, I’ve gathered some insights that I wish I could go back and share with my 20-year-old self.
Since time travel isn’t an option (yet, Mr. Elon Musk, time to get on this), I’m sharing them with you instead.
Whether you’re just starting your twenties or well into them, I hope these lessons can help you navigate this exciting, confusing, and transformative period of life.
1. Your twenties won’t be exactly what you expect
When I was 20, I had this glorified vision of what my twenties would be like.
I imagined a mix of “The Wolf of Wall Street”, “Grey’s Anatomy”, and “Suits.”
It would be a montage of glamorous parties, romantic adventures, and effortless career success.
The reality?
It’s been a lot messier, more confusing, and ultimately more rewarding than I ever could have imagined.
Yes, there have been amazing nights out, unforgettable trips, and moments of triumph.
But there have also been mornings spent crying in the hospital bathroom, stressing if I will make next month’s rent, and periods of intense self-doubt and anxiety.
What I’ve learned is that your twenties are less about having it all figured out and more about the process of figuring things out.
It’s a decade of experimentation, of trial and error, of learning who you are and what you want out of life.
My advice?
Embrace the mess.
Don’t panic if your life doesn’t look like the carefully curated Instagram feed.
Remember that everyone is fighting their own battles and facing their own insecurities, even if they don’t show it publicly.
Instead of trying to force your twenties to look a certain way, approach them with curiosity and openness.
To me, life is about experiences.
And that is my fitness philosophy as well – sometimes a nice restaurant, a cookie, or a beer with a friend is a good experience.
But the rest of the time, having good habits will give you a higher quality and quantity of life for more experiences.
So try new things, meet new people, and explore different paths.
Some experiments will fail spectacularly – and that’s okay.
It’s the failures that teach us more than our successes.
2. Make decisions for your future self
One of the most valuable lessons I’ve learned is the importance of thinking long-term.
When I was 20, I was all about instant gratification.
Why save money when I could buy those cool sneakers now?
Why study when I can go to the house party on a Tuesday?
But as I’ve gotten older, I’ve realized the power of making decisions with my future self in mind.
It’s about asking yourself, “What would make my future self proud and grateful?”, or even on a smaller scale, “What would make the tomorrow morning version of me happy?”
This applies to small daily choices as well as big life decisions.
For example:
- Choosing a salad over fast food might not be as immediately satisfying, but your future self will thank you for the increased energy, sharper physique, and better health.
- Putting in extra hours to learn a new skill might be tiring now, but it could be the difference between making $15 an hour vs. $50 an hour.
- Saving a portion of your paycheck instead of splurging on every night out might feel restrictive in the moment, but it provides financial security and options for your future self.
One practical way I’ve implemented this is by asking myself, “What is Christian 2.0 doing in this situation?” and I act accordingly.
Remember, your future self is inevitable – you will become that person.
Why not do everything you can to make their life awesome?
3. Assume everyone’s fighting their own battles
In my early (and mid) twenties, I spent a lot of time comparing myself to others and usually coming up short.
It seemed like everyone else had it all figured out – they were landing great jobs, in perfect relationships, and always looked amazing on social media.
It took me years to realize that everyone – even those who seem to have it all together – is dealing with their own struggles and insecurities.
That friend with the perfect job?
She might be dealing with crippling imposter syndrome.
The couple that seems madly in love on Instagram?
They might be going through a rough patch behind the scenes.
It’s often the people who are the loudest who are the worst off.
Understanding this has been incredibly liberating.
It’s helped me to:
- Be kinder to myself: Knowing that everyone struggles has made me less hard on myself when I face difficulties.
- Connect more deeply with others: Approaching people with empathy and understanding often leads to more authentic relationships. Seek to understand, then be understood.
- Be more open about my own struggles: Sharing our vulnerabilities can help others feel less alone and create stronger bonds.
A practice that’s helped me with this is daily gratitude.
I always thought gratitude was cliche and corny, but it’s been one of the biggest shifts in my mindset.
I am an Orthodox Christian, so I aim to pray every morning and give thanks.
Thanks for the sunshine coming into my window, for my loving wife and family, for the house I live in, for the life I’ve built, but also for the lessons from failure and hardship.
4. Try to be disliked
This one was tough for me to learn.
Like many people, I spent a lot of my life trying to please everyone.
I would bend over backward to avoid conflict or disapproval.
But here’s the truth: If you want to do anything meaningful or innovative, you have to be willing to be disliked.
Not everyone will understand or approve of your choices, and that’s okay.
LeBron James is one of the best basketball players of all time, and he is hated by many.
The president is usually disliked by 40%+ of the population.
This doesn’t mean being deliberately antagonistic or not caring about others’ feelings.
It means having the courage to stay true to your values and pursue your goals, even when faced with criticism or disapproval.
The people I admire most are the ones who unapologetically speak their minds.
Some ways this principle has played out in my life:
- Choosing a non-traditional career path after medical school, despite many criticisms from family members
- Ending toxic friendships, even though it meant being seen as the “bad guy” by some
- Speaking up about issues I care about, like balance and moderation in your fitness journey, knowing that not everyone will agree with my stance
Learning to tolerate disapproval is like building a muscle – it gets stronger with practice.
Start small: voice an unpopular opinion in a low-stakes situation, or make a choice based on your preferences rather than others’ expectations.
Over time, you’ll find it easier to stay true to yourself, even in the face of criticism.
This is a superpower.
5. You can’t fundamentally change yourself or others
When I was 20, I had this idea that with enough effort, I could completely reinvent myself.
I also thought I could “fix” coworkers, friends, or romantic partners if I just tried hard enough. Both of these beliefs led to a lot of frustration and disappointment.
The truth is, while we can grow and improve, there are core aspects of our personalities that don’t really change.
The same is true for others in our lives.
This is the nature vs. nurture debate in psychology.
Some of our personal reality is innate and encoded in our genes, while our environments shape many other aspects.
This doesn’t mean we’re stuck or that personal growth isn’t possible.
It means that real, lasting change comes from working with who we are, not against it.
It’s about becoming the best version of our authentic selves, not trying to become someone entirely different.
For example, I’m naturally introverted.
For years, I tried to force myself to be more extroverted because I thought that’s what I needed to be successful.
It was exhausting and ultimately ineffective.
When I finally accepted my introversion and learned to work with it instead of against it, I became much happier and, ironically, more successful in my social and professional life.
My close friends always joke around that, “Christian doesn’t do the things he isn’t good at”, often leading to a facade that I am good at everything.
But I’ve learned to play to my strengths while acknowledging my weaknesses and trying to learn and grow from them.
The same principle applies to our relationships.
We can’t fundamentally change others – we can only choose how we interact with them and whether a relationship aligns with our values and needs.
You can’t always choose what happens to you, but you can always choose your reaction.
6. Take risks and embrace embarrassment
Your twenties are the perfect time to take big risks.
Why?
Because generally, you have fewer responsibilities and commitments than you will later in life.
The cost of failure is lower, and the potential payoff of success is huge.
People fundamentally value relationships and money.
But, most people don’t have families or significant savings in their 20’s.
Why not take a risk?
But here’s the catch: taking risks often means facing the possibility of embarrassment.
And let’s be honest, embarrassment feels terrible.
It’s why so many of us play it safe.
I wish I could go back and tell my 20-year-old self: embrace the embarrassment.
It’s a sign that you’re pushing yourself out of your comfort zone, which is where real growth happens.
Some of the best opportunities in my life have come from taking risks that could have (and sometimes did) result in embarrassment:
- Quitting practicing medicine in favor of starting my own business (it worked and I’m happier than ever)
- Performing karaoke at a bar with friends (you do NOT want to hear me sing)
- Expressing my feelings to my best friend (who is now my wife!)
A practical tip: try the “5 Second Rule” popularized by Mel Robbins.
When you have an impulse to do something that scares you, count backward from 5 and then take action before your brain can talk you out of it.
7. Most relationships are temporary, and that’s okay
When I was 20, I thought every friendship and romantic relationship would last forever.
I had some core homies that I grew up with and inseparable friendships that I was building in college.
I put enormous pressure on myself to maintain every connection, even when it was clear we were growing apart.
Now, I understand that most relationships serve a purpose for a specific time in our lives, and then naturally come to an end.
This doesn’t make them any less valuable or meaningful.
Think of relationships like seasons.
Some are like summer – bright, intense, and seemingly endless while you’re in them.
Others are like autumn – beautiful but clearly transitional.
A few are like winter – challenging but potentially transformative.
And some rare ones are like spring – representing new beginnings and lasting growth.
Very philosophical, I know.
Learning to appreciate relationships for what they are, when they are, without trying to force them to be something they’re not, has brought me a lot of peace.
It’s allowed me to fully enjoy connections while they last and to let go with gratitude when it’s time.
This perspective has also helped me to be more present in my relationships.
Instead of constantly worrying about the future of a friendship or romance, I try to appreciate the connection for what it is right now.
8. Hold your dreams lightly
Having dreams and goals is essential – they give us direction and motivation.
But it’s also essential to hold onto them lightly.
Why?
Because sometimes, achieving a long-held dream doesn’t bring the happiness we expected.
Other times, we may need to adjust our dreams as we grow and change.
I had a dream of becoming an orthopedic surgeon and having my own surgery center.
I worked hard towards this goal for years.
But when I finally was working in a similar environment in medical school, I realized it wasn’t what I truly wanted.
I had changed, but I had been so focused on achieving this dream that I hadn’t noticed my values and interests shifting.
The key is to focus on enjoying the journey and finding meaning in your daily actions, rather than pinning all your hopes on a specific outcome.
Some ways to do this:
- Regularly reassess your goals: Are they still aligned with who you are and what you want?
- Celebrate small wins along the way: Don’t wait to reach the “final destination” to feel satisfied.
- Be open to pivoting: If a dream no longer serves you, it’s okay to let it go and pursue something else.
You invented your dreams, which means you have the power to reinvent them too.
9. True self-esteem comes from your actions
In my early twenties, I thought that achieving certain external markers of success – a high-paying job, a nice house, a large social media following – would make me feel good about myself.
But even when I achieved some of these things, the boost in self-esteem was always temporary.
This is the hedonic treadmill.
The hedonic treadmill, also known as hedonic adaptation, is the observed tendency of humans to quickly return to a relatively baseline level of happiness despite major positive or negative events.
What I’ve learned is that lasting self-esteem and happiness come from consistently doing things that align with your values and make you proud.
It’s about the person you are and the actions you take, not the things you have or the approval you receive from others.
This can include small daily actions like making your bed, keeping your promises, and being kind to others.
It can be embracing personal growth like earning new skills, facing your fears, or working on your mental health.
There is also a component of contribution: Volunteering, helping friends, and creating something that adds value to the world.
A practice that’s helped me with this is keeping a to-do list.
I use an app called TickTick (not sponsored) to schedule work tasks, chores, or events.
As I go through each task, I check off completion and at the end of each day I see all I’ve accomplished, no matter how small.
It helps me recognize the positive actions I’m taking and builds my sense of self-efficacy over time.
10. At some point, the party lifestyle loses its appeal
When I turned 21, I thought the party would never end.
Nights out, festivals, social drinking, and the occasional hangover were just part of the lifestyle.
And for a while, it was fun.
But there came a point – different for everyone, but it happened for me around 25/26 – when this lifestyle started to lose its charm.
The hangovers got worse, the conversations at concerts started to feel repetitive, and I found myself craving more meaningful (and healthy) experiences.
If you’re in the thick of the party phase, enjoy it!
But also, pay attention to when it stops being genuinely fun and starts feeling more like an obligation or a habit.
It’s okay to outgrow this phase and shift your focus to other pursuits.
In fact, it’s a normal and healthy part of growing up.
Some signs it might be time to reevaluate your relationship with partying are that you’re not enjoying it as much as you used to, it’s interfering with other goals (career, health, relationships), and you’re doing it out of habit or to avoid dealing with other issues.
Remember, evolving your lifestyle doesn’t mean you can never have fun or go out again.
It just means finding a balance that aligns with your current values and goals.
Conclusion
Your twenties are a time of immense growth, change, and self-discovery.
They’re messy, confusing, exciting, and transformative.
Embrace the journey, with all its ups and downs.
Remember, it’s okay to make mistakes – in fact, it’s through those mistakes that we often learn the most valuable lessons.
Stay curious, keep growing, and be kind to yourself along the way.
And hey, if you’re past your twenties and reading this, it’s never too late to implement these lessons.
We’re all works in progress, constantly learning and evolving.
Your future self is rooting for you – go out there and make them proud.
If you’re interested in more tips related to becoming a top tier human, fill out my 1 on 1 coaching application from the button below to become fitter and healthier – guaranteed in 90 days.
All the best,
Dr. Christian