Are You Really Challenging Yourself? Really?

Throughout my life, I have always sought out challenges, but my reason for doing so has completely shifted over the years. 

I’m not embarrassed about the fact that I was very insecure when I was younger, because that insecurity often propelled me to try to prove myself rather than shying away. I was constantly trying to prove to other people in my world that I was enough, and I was trying to convince myself that I was enough, too. But in every avenue, whether it was my dating life, my school life, my athletic life, or my professional life, I never really got there. I spent my teens and twenties trying to  push myself as hard as I could, and it's only been very recently that I've managed to reframe the way I challenge myself. 

Now, I challenge myself because I fundamentally love myself. Now, I challenge myself because I know I have worth and I am capable of rising to those challenges. Now, my challenges are exciting, additive processes as opposed to a frantic scramble in which I’m trying desperately to prove something. 

Through this transformation, I have learned 6 key things about challenges, to the point where I now seek out the ones that seem just slightly out of grasp. I look at it this way: If my odds of failing are 95 percent, and I do indeed fail, it’s okay. But if I win, I somehow have surmounted the odds, and my challenges then set myself up for a far more satisfying conclusion.

You cannot challenge yourself effectively from a place of self-hatred.

You might be temporarily motivated to change if you hate yourself, but doing so is fundamentally unsustainable in the long run. You can only sustain a level of self-hatred and frustration for so long. I know, because over the past year or two — between entrepreneurship, a serious relationship, and a move across the country, among other stressful things in my life — the self-hatred became too much for me to bear. I would not have survived many more days of starting every day with the assumption that I'm losing, or that people don't like me and I'm not good enough.

All of this negative talk stemmed from my mood disorder: I have what's called dysthymia, which is a low-grade, constant depression. Mostly when people think of depression, they think of major depressive disorder, which occurs  as a very serious mental health crisis for a few weeks or a few months. I had my one and only MDD episode last summer, where I could barely get out of bed for two or three weeks. That was sort of the beginning of the end for me, and that was when I really started making big changes in my life, and committed myself to working from a place of self-love. Maybe to an outsider, like my day-to-day schedule looks similar, but how I'm conceptualizing that schedule and experiencing that schedule couldn't be more different. 

Reframe your mentality so that you're not starting with the assumption that you're worthless and then trying so desperately to prove otherwise. Start instead with the assumption that you're wonderful the way you are, and that you enjoy the process of trying to improve. Perhaps that effort amounts to the same end goal, but it's a 180-degree rotation in terms of how you conceptualize the framework. 

You need to seek out the challenges that harden you.

I often think of challenges as a matter of fitness: When you go to the gym and exercise a muscle, it will tear, repair itself, and come back bigger and stronger. That's how you can lift heavier and heavier weights, or run faster each time. You condition your body to be able to handle the strain so that you can push yourself and handle a larger strain next time. 

The mind works in much the same way. By challenging yourself, you adapt as a human being. You learn how to either get better, or handle not being good enough, or both. One of my favorite psychologists says that we don't get less afraid, we get braver. So if you're afraid of things in your life and you work on it, it's not that you're less afraid of them. It's just that you are more brave and can take on those challenges. Any challenge psychologically makes you a little bit stronger so that you can either take on that challenge and win or take on a bigger challenge and lose, which in turn will make you stronger.

Your challenges will not look like anyone else’s challenges. They shouldn’t.

Right now, the world is challenging. It has always been challenging in a myriad of ways. If we were born two generations ago, we'd be worried about getting drafted and going to Vietnam or World War II. Now, there are so many things that we have to grapple with that our great-grandparents couldn't even possibly comprehend, like imminent damage from global warming, the effects of technology on our psyche, and depression and anxiety being at an all time high. There are so many problems that are unprecedented or at least the worst they've ever been — but there are also so many things that are the best they've ever been. 

I'm not here to be the judge and jury and say that we have it easier or harder than another generation. I think it's hard to really put everything onto one definitive scale and make that assessment. But I think it's fair to say that like anyone living, ever, has challenges, no matter how rich or how poor they are. The challenges certainly look different, but they are there in every life. And in some ways, we all are blessed — just about everyone can find something in their life they love and can feel grateful for.

It’s because of this that I think we all can chart a path from where we are and what we're grateful for to where we'd like to be. No two journeys will be the same. A billionaire’s path from where they are to where they want to be will obviously be worlds apart from someone who lives at the poverty line.  But you can feel happy and fulfilled through the act of loving an aspect of who you are and where you are and charting a path to a version of yourself that is a little bit higher than where you are today, irrespective of where you're starting and ending.

You can harden yourself without forgetting what makes you, who you are.

As the saying goes, you should never forget where you came from. When it comes to your emotional work, I believe doing so keeps you humble, and reminds you about the journey that still lies ahead of you.

I have one of the most active minds of anyone I know, which is often my demise and my greatest weakness, as well as a strength. My mind moves very fast and I'm always thinking and worrying and checking in and observing. When you add that horsepower to a talk track that tells you all the ways you’re not good enough and that you need to do more, for decades, it is very hard to shake. 

I know because that was my talk track. I was in the gutter of my emotional spectrum for a long time, and I can still feel the shame it brought up. For me, getting harder and improving means beating this demon, and paying that work forward. I get immense satisfaction trying to help people that are on their journeys and maybe haven't quite figured out quite as much as I have. That is my way of remembering where I came from, and it’s driven by my empathy, my love of others and myself, and my sensitivity. These will always be my hallmark traits, and I intend to use them to help people who are where I’ve been, for years to come.

Recalibrating your challenges for your skill set in the moment does not mean you’ve failed.

For the past couple of weeks, I’ve been living in a shipping container in North Carolina, and I have all these goals written on stickies on my bathroom mirror. Some are about trying to get in peak physical shape, while others are to read more, and to meditate and to hit goals at work. But over time, I’ve realized I went too wide. My whole day was spoken for, and because I was too regimented, I was slipping back into a self-hating mode again. No matter how hard I tried, I ended every day feeling like I hadn’t accomplished something or like my effort on a given task hadn’t been so great. As a result, I pulled myself back and I’m now finding a balance of how much challenge is enough and how much is too much. 

This is normal. If a challenge is too hard, you’re going to lose focus. If you think about a grayhound dog running around a track, there’s always the rabbit that is just out of reach. If the rabbit gets out too far ahead, the dogs will lose interest or pace, or they might get distracted. If the rabbit's too slow, then the greyhound catches the rabbit and it's over. 

You need the challenge to be out in front just enough that it's pulling the best out of you always. If it's too far ahead, it can be demoralizing or you lose track of it, and if it's too easy, then you don't get the same sense of accomplishment. Right now, I'm trying to find a balance of sort of being enough and being not enough, and living in that paradox. How can you love yourself and know that you are good enough just as you are, while simultaneously knowing that you could also be better and take on a challenge in which you might lose?

My goal right now is to live every day in which I can easily think, “Hey, I'm pretty great, and I'm happy with where I am and who I am and what I'm doing. I'm lucky to have the life I have and to be the person I am. I'm enough.” But then I also hope to say, “Wow, the work I’m doing is really hard. I don't know if I'm going to be able to accomplish this.” I think you need that tug of war, because I think that forces you to get better on a timeline that is both manageable and sustainable.

The point isn’t always to accomplish something. The point is to challenge yourself.

I'm really good at setting goals and putting a system in place to chip away at it for one to four weeks. Sometimes when a goal is eight or 12 weeks away, it gets a little bit in front of me and I lose focus. That happens because I am human, and no one person is going to achieve their goals perfectly every single time.

I'm not here to say that I'm some hardened warrior that has it all figured out and hits every goal he sets. More often than not, I do not hit my goals. And I'm not embarrassed to say more often than not, I quit before it's over. It's not that I try to run a mile at a certain pace, and I just miss the deadline. More often than not. I stopped training after four weeks because something else came up. 

Sometimes I beat myself up for that, and sometimes I feel like the most important part of the process is seeing something in yourself that you love, seeing how you want to improve it, setting a goal and starting to take the first couple of steps along the path. Imagining yourself in a future state and starting the process is more than half the battle.

As in so many things, challenging yourself is all about the journey, not the destination. Ideally, you would accomplish some or even many of your goals, but I think it's okay if you don't. Starting is more important than finishing, because so many people aren’t even brave enough to try.