The curse of moderate success

May, 2009: It was advice I didn’t want to hear. I was trying to start a business and busy dreaming of a comfortable life – one with a nice apartment, vacations in Costa Rica and an exotic sports car. J*, a trusted mentor, turned to me said, “You know Jason, if you do become successful, you can’t get too comfortable. Comfort is the enemy. A little is deceptively dangerous; a lot will stunt your growth. Someone who’s hungrier and more driven will overtake you. Comfort will kill your lust for life.”


One thing that no one mentions is that moderate amounts of success can – and probably will – sabotage you. It’ll hold you back more than the fear of failure ever could. This is especially true if initial success came quickly for you; the same success you fought so hard for risks stunting your growth. When I think about the ways I could derail my life, becoming too comfortable and too complacent tops the list. Here are the demons I look out for:

Earned laziness preventing me from working hard. In most cases, finding initial success requires endless rejection, false starts, loved ones trying to ground you, navigating an unruly marketplace, and your own inner critic doing her best to fuck your shit up.

But along with that sense of achievement that comes with beating the odds there’s often a subtle sense of earned entitlement. You’ve given everything you have to give, and you’re at the top of the game. It doesn’t feel like you should have to keep working, fighting, doubting, and risking it all anymore. It feels like you should be done, like you should already have the relationships, skills, reputation and knowledge to open any door.

Unfortunately, that’s not the case. What got you here won’t get you to your next destination. You’ll have to return to being a beginner, being humble, moving slowly and getting crappy results for months or years on end. You’ll be less successful than the people around you again. You’ll have to let go of the sense of being on top of the world in order to create the mental and emotional space you’ll need for even bigger battles.

You once told yourself that anything worth having doesn’t come easily. That allowed you to keep working and get to where you are now. For better or for worse, that still rings true.

The hidden fear of losing myself makes it easy to perpetually focus on something else. As you know, leveling up will require sacrificing a lot of what you’ve already built. I know from experience that it sucks. I spent nine years building my speaking practice. At the top of my game, I was one of the best in the market, but I scrapped it to build my consulting practice. It took me four years to build that business. Now, I’m scrapping that too, because my heart’s no longer in it. I kind of feel like I’m losing pieces myself as I sacrifice old projects to start new ones. It’s destabilizing and scary.

Yet the fact remains: you’re going to have to do the same damn thing. If you’ve identified yourself with your current success (and who hasn’t?), then it’s going to feel like you’re losing yourself as you grow into your next project. But creation can’t be untethered from destruction. That’s just the way it goes.

Perhaps even more frightening, you’re going to have to deal with rejection again, too. If you want to grow, you’ll have to jump right back into the fire. It’ll be painful, but it’s less painful than stagnation and frustration.

Of course, you’ll fight against this. You’ll tell yourself that since you’ve become successful, it’s unacceptable for you to put out anything besides perfect work. Obviously, this is nowhere near true. The only path forward is to do your best and polish up in real time. Don’t worry, if you’re dedicated enough, you’ll be fine.  

I’d love to be able to give you life hacks or something that would allow you to avoid facing these fears. But you and I both know that these are demons you’ll have to stare straight in the eye (and do your best not to blink). The good news is that you’re perfectly capable.

Comfort enables me to keep pushing off my next dream. When you first built your life, you may have felt fear and entitlement, but you mastered them. You had no other choice. You were hungry and that was enough to fire you forward. Now you’ve got enough time, money and status to keep you happy(ish). Where there was once a burning hunger that fired you forward, there’s now comfort – maybe even a sense of responsibility. If you really want to own your next great adventure, you’ll have to sacrifice the comfort that keeps you immobilized. I don’t mean that you need to give up your nice home, dinners out or your social life. What I mean is that you’ll have to notice the tension and resistance in your body that begs you not to start the new project. You’ll have to notice your mind sabotaging you with compelling arguments in favor of procrastination. And when you notice these things, you’ll have to fight against them again, and again, and again.

So, how do you overcome the curse of semi-success?

The good news is that the curse of comfort and semi-success is one that you can break. Here’s one way of doing it:

Take some time off. Like a month or two. Travel, learn an instrument, stay at home and rest, whatever. It doesn’t really matter what you do, you just need to remove yourself from your work and routine. This will help you regain your identity as a creator, a fighter, and a risk taker. It will allow time for your next dream to take residence in your heart. Perhaps most importantly, it will give you a moment to rest. The battle in front of you is real. You’ll win, of course, but you’ll probably have to leave it all on the field. Don’t worry. You’ve done this before, and you can do it again.

Allow new motivation to take over. In the past you were able to motivate yourself with raw hunger, but you can’t do that anymore. You’re too successful. You need to find something different to inspire yourself. Personally, I like to spend time imagining two different realities. First, I vividly imagine embracing my dream life. I try to generate feelings of excitement and gratitude for the life I want to create. Then, I try to imagine what would happen if I fail to act on my dreams. I try to generate feelings of fear, depression, and regret. The sharp contrast of my dream and nightmare makes it easier to take action.

Some people find it motivating to spell out their vision for themselves. If you’re one of those people, I highly recommend Cameron Harold’s book, “Vivid Vision.

Now return to the game. What did you do last time that enabled you to succeed? Did you apply to 117 jobs and move to Colorado? Did you do 50 cold calls a week? Did you go back to school even though you were a decade older than your classmates? Whatever you did, you needed courage and dedication. While the path may be different this time around, you’ll still need the same fuel. Your only job is to keep putting one foot in front of the other and refusing to accept failure. Depending on how you look at it, it’s as easy as that, or as complicated as that. The trick, as always, is to fall in love with the process.

PS: An entirely different solution to the curse of semi-success

There is a different approach to dealing with semi-success, and it’s one I’m a big fan of. Learn to be content with what you have. It’s already more than enough. What will your next big victory really do for you anyways? You don’t actually believe that more money1, more status, a bigger home, a hotter lover, or more fame will change anything for you, do you? Chances are they’ll just further fuck you up.

If you’re hunting success for the sake of validation, then you’ll never have enough. I’ve fallen into that trap dozens of times in my life. While falling in love with what you have may prove just as hard as becoming more successful, it’s almost guaranteed to be more satisfying and meaningful.


  1. Obviously, for some people having more money is the solution. If you aren’t able to easily meet your basic material needs, then I hope that that changes for you soon. Perhaps more importantly, if you are able to meet your basic material needs, I urge you to help others who aren’t as fortunate. This can be through loans, education, mentoring, donations, whatever. One thing I can promise you: investing in the success and stability of someone who needs help will bring you much more meaning and satisfaction than the mundane act of leveling your own life up.

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