This post is about how to find success in any situation and draws entirely from my own experiences. Your mileage may vary.

July was a rough month for me this year – I endured simultaneous failure on all fronts. I had put on a shitload of weight, ended a relationship, and market conditions changed unfavorably for MarkedUp. All of this occurred within a couple of weeks at the tail end of the month.

I am well-accustomed to stress and handle it well. I’ve had things not go my way before, and I’ve always found my footing again.

This time something was different. Maybe it’s because of how deeply invested I am in MarkedUp or because of everything going wrong at once, I don’t know. But the difference this time I walked away with a major dent in my self-confidence and self-sureness. That’s a new one.

I wasn’t even aware that my confidence took a dip at the time. I figured that out more recently, when I started noticing a huge increase in my anxiety and apprehension when it came to routine things.

I started asking myself, “wait a second – this shit never used to bother you. What’s changed?”

Then I remembered the truth. Let’s flash back a few years.

An Unusual Habit

I was an immensely awkward kid my first two years of college. You know the formula: under-socialized kid who spent more time in front computers than people during his developmental years suddenly thrust into a co-ed dorm with babes and booze aplenty, 2,000 miles from the nearest person he knows, unsure of himself, finding his way in the dark.

In particular, I was utterly terrible with women. Terrible enough that my Freudian defense mechanism kicks in with full force when I try to relive the full horror of my own awkward blunders with the opposite sex. Jesus.

Second semester freshman year, I discovered alcohol and spent more time partying1 than studying, receiving poor grades for the first time in my life.

When Sophomore year rolled around my advisor put the ever-loving fear of God into me that if I did not clean up my act then there was no chance I’d ever make it to a decent Computer Science graduate program. I immediately dropped the partying and focused on my school work, and somehow my social life managed to get even worse than it was the year before.

Worst of all, my grades improved but not by a big enough margin to move the needle. I still wasn’t succeeding. Failure on all fronts. Sound familiar?

So I made a decision.

At the very end of Sophomore year, I signed up for study abroad the following summer in Berlin, during the 2006 World Cup.

None of the people on that trip from Vanderbilt knew me, and certainly none of the other students in Berlin. I had a clean slate, and since I had fucked my last one up during freshman year of college, I was going to do things right this time, damn it.

The decision I made was simple: I would not give a single iota of shit about my schoolwork and not take myself seriously. And drink beer. Can’t forget the beer drinking.

The results were astonishing: I had an easy time making friends, socializing at parties and clubs, and my grades were actually pretty good to boot. FWIW, alcohol tolerance was insane by the time we left Berlin, but we’ll save that story for another time.

So I doubled down at the start of junior year. I decided I would not care about anything other than getting the most out of my college experience. I joined a fraternity, took graduate-level courses, dated some fun and interesting women, and pretty much felt like a bad ass. My GPA junior year was a 3.8 – and the amount of effort I put into my schoolwork was a fraction of what I had put in the year before.

Senior year, same thing – I stopped giving a shit about everything by default and with the confidence that I could turn any situation in my favor when I needed to. And I did.

By the time I left Vanderbilt, I felt like a bad ass. But when I entered the real-world and got a job, everything changed. I had to start all over again and build myself back up piece by piece.

Set Your Own Odds

The point of that story is that my ability to succeed personally, physically, and professionally was inversely related to my level of emotional investment into whatever I did. It was that way all along.

I still put in a lot of hours on my school work, I worked out often at the gym, and I spent a lot of time trying to come up with fun ideas for dates.

I put a high level of effort into things that mattered, but for very different reasons than my freshman and sophomore year. I put effort into those things because I wanted to, not because I felt like I needed to.

Not giving a shit simply means doing what you want to do without any emotional investment in the outcome. Put differently, you gradually develop habits to counter your mind’s self-protective “flinch” reflexes.

Negative outcomes and consequences were still possibilities with everything I did, but I hardly thought about them. After all, I live in a part of the world where it’s considered a really bad day if you lose Internet access for 24 hours – what’s the worst that could happen, really?

Once you stop worrying about the negative possibilities, every opportunity has nothing but upside. Ask the cute girl / guy at your gym out for drinks – the worst thing that can happen is a slightly awkward story that you and your friends can laugh about over drinks later. It’s all upside from there.

Stop giving a shit. Stop caring about what other people will think about you if you fail. Worry only about what you’ll think of yourself if you don’t try. No one likes a pussy.

Bold without Knowing It

So, jumping back to the present. Once I realized what was going on, I ran through my process for putting my brain back into “don’t give a shit” mode:

Work towards concrete goals – we can’t control our calendars and circumstances at every given moment, but we are always in charge of deciding what’s important to us. Remember what those goals are. Create a path for realizing them. All of them. Follow it. Even if it takes years. Ignore everything else.

Step into every punch – an old boxing metaphor; if you’ve ever tried boxing, your first natural reflex when someone tries to punch you in the face is to jerk your head back out of the way.

If you let that happen, you drop your cover and leave your face exposed, which allows experienced boxers beat the shit out of you.

So the antidote is to train boxers to step into their opponents’ punches with their guards up and use counter attacks or controlled evasions, instead of flinch reflexes.

The same goes for every day life – when your chest tenses up right before you send a critical email, condition yourself to just press send and don’t think twice. Do the opposite of what your pain-avoiding reflexes tell you.

Practice taking risksread my full post about the subject. Start habitually taking risks on small things, so you’re prepared for the really important stuff in the future.

Decide how you want to react to things – from the Seven Habits of Highly Effective People: “you can’t control everything that happens, but you can always control how you react to them.”

My (chosen) default response to most things: “meh.” Celebrate victories and learn from defeats, but don’t dwell on either.

Find the upsides – as mentioned earlier, every day risks offer very little for us to be afraid of beyond mild embarrassment and maybe some financial / temporal setbacks here in the comfortable first world. So look at your opportunities, even the small ones, and use the upside as your primary decision making metric, rather than fear of failure. You’ll make bolder, better decisions that your 80-year-old self will appreciate.

Find the things you like about yourself, then show them off – there’s an engaging, interesting person inside all of us. Find him or her and let the rest of the world in. Me? I’m pretty sure I can make just about anyone laugh.

So even though this post makes me feel a little vulnerable and reads like dust jacket of a self-help book, I’m publishing it anyway. If it helps someone else find their stride, that’s all that matters to me.

Nothing ventured, nothing gained.


1FWIW, my social skills did not improve as a result of said partying

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