How To Find Happiness (In Your 20s and Beyond)

Even though you’re entering this exciting time in your life as an adult, your 20s can be very lonely. That doesn’t often square with the way people talk about the decade as being the best time of your life. You have this nexus of power and autonomy, with very little responsibility, the way you probably would when you’re older. Your 20s are an in-between time: When you're 18, you live in your parents' house and you have to do what they say. But when you're 24, you live by yourself, you’re making some money, and you can do whatever you want. You don't have to be home to put the kid to bed or to walk the dog. People think that kind of freedom will bring you happiness.

That isn’t always the case for everyone. I’ve had very bad depression at moments, and if it weren’t for medication and therapy, I’d always feel less happy than I do when I’m on the regimen that works for me. Yet I also think we all with very few exceptions actually have more control over how we feel than we realize. You can take ownership of yourself and not resign that sovereignty to some sort of group identity — that you’re unhappy because you’re a member of this group. 

I think part of happiness is taking responsibility for your happiness, and that you have more sovereignty over your plane of reality than you previously realized or were taught. Happiness in your 20s is about saying, “I have control of myself and I can move along a continuum and become happier every day.” It’s about taking the opportunity to ask the harder questions about what actually drives you and trying to find happiness in even the most regressed state. The people that can find strength within themselves are, in my experience, the happiest people I know. And if you do the work right, that can start the day you become an adult.

Unlearning and Relearning Everything You Thought You Knew

Something I say a lot is that there are two deaths that need to happen in your 20s. One is the death of your parents as an infallible North star, and the second is death of ego and self. 

Sometimes these deaths occur in your teenage years. I experienced them in the final months of my 29th year — I was just sneaking it in. You’ll realize your parents and other role models may be well-intentioned people who love you — but their sense of reality; rules; and rubric for success, happiness, meaning, and life isn't necessarily capital-T True for you. In other words, once you get out into the world, you realize there are other ways of viewing things. Embracing the reality that “my parents don't know everything” frees up some space to question, “What are the rules?”

Then, what you realize is that unfortunately your conceptualization of the rules in your 20s often mirrors how you were raised. So you kind of need a death of self where you meaningfully challenge some things you've taken as given before, and you sort of kill off aspects of yourself that were always meant for someone else. You start to tune in and trust your voice instead of subjugating it. 

Especially now, everyone is questioning the things that we were taught as being capital-T True: Our democracy is good, capitalism is good, our political system is good, our healthcare system is good. Our generation is more progressive than we have ever been, and the people younger than us are even more progressive than that. We are fundamentally doubting the big tectonic plates that sit underneath our society right now. People our age are questioning if we want to live in big cities, or if we want to get married or have kids. The American dream of old is being thrown out, questioned, chopped up, and changed. It’s uncomfortable and weird and bizarre and sort of dystopian, but it’s also very healthy. And this is the time you can grow into not only who you have always been — but who you are truly meant to be.

Breaking Free of Patterns That Drag You Down

There’s this American drum beat of capitalism: If you're lucky, go to college, get a job, pay rent, buy a house, have a kid, pay your mortgage, save money, send the kid to college, keep working, save more, pay off the mortgage, retire. And I think there are a lot of opportunities along the way to say, “I am a victim to this. I have no sovereignty.” It’s kind of like an obligatory march to your death. 

It’s also a very convenient way of thinking, and you can hide a lot of self-hatred in that. Blaming the job you hate or the partner you don't really love or the money that you don't really have are very convenient things to point to as to why you're not happy. But just by trying in small ways to improve your situation and take ownership of how you feel, you can make major shifts. We often think reality happens outside and then our brains react to it. But what if our brains react to things which creates the reality outside? The more I tap into that self-determination, the happier I am.

I don't think I've wasted time or lived a terrible life, but I've only very recently started loving myself. I didn't really know exactly who I was or exactly what I cared about. I knew the broad strokes of what made me happy or unhappy, but I think I was pretty numb. If I could go back in time and undo some of the damage I was doing to myself, I would. So much of my energy in my early 20s was dedicated to just beating myself up. But I also know that I started my company, The Hub, out of self-hatred, and to prove that I was worth something and a lot of beauty has come out of that, including for my coworkers and the photographers and brands we help. 

My therapist always says, “Any therapist worth their salt is trying to fix some part of themselves, too.” I know that a lot of my self-hatred and how hard I was on myself earlier, made me forge this path forward and help make things better for everyone.  

Understanding the Difference Between Unhappiness and Depression

I have the enormous benefit of being able to talk about my depression without shame.  I don't think that you can will your depression away, because Lord knows I've tried. Medication and therapy work for me. And what a gift that I've been born in this age where I can talk about that openly and not be fearful of judgment. 

I have changed a lot of things about my life in the past few months especially. I spend hours a week in therapy. I work really, really hard on my mental health, but if I lower my medication, I feel depressed. I'd like to think that I have complete autonomy over how I feel, but there’s something biological in my depression, which we as a society do not fully understand yet.

Even so, I don’t think happiness and depression are at odds with one another. I view depression as a chemical, biological thing, and happiness is a layer that sits on top of that. Depression and sadness are not the same thing, either, and like being manic is not the same as being happy. 

More people than ever are depressed or anxious. One out of eight American adults have a benzodiazepine prescription. And there’s something to be said for sitting in the blockage of unhappiness or of depression for a second, and just feeling what you're going to feel before reallocating it to something more productive.

The key for me in being able to move on, rather than sitting in a depressive spiral, is to focus on self-love. It's really hard to be at peace with yourself. But if you do get there, a lot flows out of that. You're more patient and understanding of others, and you have so much more room to allow other people and other things to do what they must. If you don't get certain things you wanted, or someone wrongs you in a way that you weren't expecting, you can still be at peace with yourself.

Letting Go of How Other People Perceive You

There's this quote I love: “I am who I think you think I am.” The idea is that we all live in our heads and we're worried about our perceptions of others' perceptions of us. Often you might worry that the person you're on a date with thinks you're really dumb or that your mom thinks you're failing at something, but that's your perception of their perception. By embracing a death of ego, a new view outside of that perception can be born. And you can more closely listen to your voice and some of the signals that your body and mind give you, sort of like an antenna.

If you’ve ever experienced depression for a long period of time, you know that you tend to get really sensitive. That antenna gets very, very adept at feeling subtle movement in your happiness. You might start to feel like you’re going crazy because everything affects you, but I think paying attention to that antenna is useful. It helps you attune to the things that make you happy and why.

Trusting your voice and your instincts when something makes you uncomfortable helps you ask hard questions: Does this make me happy? Why or why not? If it doesn't make me happy and I have a good reason for it, can I remove it from my life? Do I have the luxury to do that? And I would argue, the answer is almost always, “Yes, you can remove it.” If you want it badly enough, you can find a way to cobble together some extra money to quit the job that's super toxic and still make rent. If you're going to leave your romantic partner, you can find a way. There are exceptions that I accept, but I also know that people are more resilient than they realize and have more options than they realize. 

Humans recalibrate to almost anything in about three months, barring pretty acute trauma. Gaining or losing a romantic partner, getting a promotion or getting fired from a job — these are big life events for most of us. And we think they're going to have outsized impacts on our happiness, but they actually don't. Within three months of gaining or losing a romantic partner, getting accepted or rejected to a college, getting fired from your job, getting a promotion, you will be on average exactly as happy as you are today. 

So why not find a way to divest from what is dragging you down right now? In three months, the trauma associated with doing so will often be gone. And you have the chance to be infinitely happier, even after the immediate pain you incurred in letting go of that which does not serve you anymore. 

Using Your Time to Simplify What Makes You Happy

Something I’ve noticed about COVID is that, for those of us who aren't having a terrible health or financial crisis, we’re experiencing some kind of pause wherein many of our outlets are no longer available to us. Last year, you could go out for drinks with friends, or go to a museum, or go to an exercise class. You could spread your energy out so liberally. But when you wake up constantly feeling hollow, you don't really know why. 

Now, we can't really socialize. There’s no dating, no exercise classes. A lot of the ways you might have spent your time before are now gone, and you’re left to sit with yourself and with a few simple truths. And suddenly, the equations for happiness become much simpler. I'm happier now than when things are more complicated. I have less to distract me, and less to regret. There’s no more thinking, “Maybe I should have done this with my Tuesday night,” or, “I'm a loser for staying at home alone.” I’m currently living in my parent’s house, alone, doing nothing. And I don't feel like a loser because there really isn't an alternative. This is just my reality and I've come to really love it. 

In the moment, having the ability to choose what you do feels like it's a good thing. We all want and seek out choice. But the more choice you have, the more opportunity you have to regret your decisions. If you have no say in the matter, you actually are happier. 

I also think another benefit of simplifying your happiness is the ability to compound and diversify the things that make you happy in small ways, just like you do with money. There are lots of value stores in life, including your professional fulfillment, your relationship with your significant other, your hobbies, and your friends. These are all things that can bring you happiness, but you only have a finite amount of time to focus on each of these stores. 

If you spend all your time at work, you spend less time with your significant other. If you spend all your time with your significant other, you spend less time at work. So just like you move money around, you can move your happiness around and invest in things and divest in things that make you happy. Again, it’s about listening to your antenna: Pay attention to what brings you happiness and invest in those things that do. Divest from those that don't. 

Putting a Premium on The Things that Make You Feel Fulfilled

For me, the act of challenging myself and making progress is very central to being happy. I think we die inside when we're not challenged. I thrive when I’m working on something that is a bit too hard, and that I wonder if I’m not quite good enough for it. I need to better myself and challenge myself on a fairly regular, if not daily basis. Relationships or jobs or hobbies can all create that friction, but you need that thing in your life that brings the best out of you. Otherwise you just sort of atrophy.

I think a career has played that role for a lot of people, historically, but if you can’t find happiness in your job, I recommend you find a damn good alternative. If you're miserable at your job, how can you find fulfillment elsewhere? How can you find challenge and intrigue and something that brings the best out of you? 

A reality for some people is that they go to work to make money, and that’s fine. But if you hate what you do, you’re spending a lot of time on something you hate. If that’s the case, I hope you can find things that really fill you up — whether it’s a really meaningful relationship or hobby that you can’t wait to get back to at the end of the day.

Gary Vaynerchuk says that living for Friday is like a pretty shitty construct. This thing that we do societally, where we’re like, “The week is almost over, thank God for that. Now I can get to doing what I really love.” But if you want to be happy during the week, I want you to think about how can your Tuesday be something to live for, too? How can you make it so that you're really stoked to wake up on Tuesday or Wednesday or Thursday, for that matter? Why do you only have to save the things you’re happy about for the weekend?

There are healthy ways to fill holes and unhealthy ways to fill those holes. I think there's something to be said for sitting in the uncomfortability of your unhappiness, because that can spur you to create meaningful change. I also very much believe in the paradox of being enough and not enough at the same time: Being not enough is when I wake up and I feel that I could be a better brother, son, boyfriend, entrepreneur, human — you name it. That drives me forward and makes me show up for all my relationships, and as a boss and a business leader. But you also need to be able to sit with yourself and love yourself and feel that you are fine just as you are — to feel that you are enough. 

I know I want to better myself and grow and progress, but I also know I operate better when that space comes from self-love. You have to have room for a deep hunger for self betterment so that you can improve and help others. But you also have to have a love of self and a contentment of where you are and gratefulness for where you are. It’s hard work, and it’s a constant fight. But it’s doable, if you commit yourself to putting in the work to better yourself. I’m still working at it every day. But I know that work is worth it.