From an emotional standpoint, startups are really, really hard. Every day I’ve faced emotions and challenges that are completely new to me – hiring, setting company strategy, motivating a team and making product decisions.
On top of the emotional challenges, part of your “job” in a startup is to stay current with the latest technologies, startup advice, Paul Graham’s essays and things happening in startup land. As part of this, you will hear about people far more successful than you are. Far, far more successful. And sometimes, it kind of sucks.
It can be easy to occasionally feel envious or jealous of other’s success. Not a constant, obsessive feeling or anything like that – just enough of a problem where I recognize that this is something I have to deal with. Where I’ll read something on TechCrunch and think “wow look at how successful company x is.” I haven’t seen much written about this, but suspect (due to conversations I’ve had with other founders) I’m not alone in thinking/feeling this way.
After dealing with this for about a year, I’m doing far better. I rarely now experience feelings of envy for other’s successes, though some weeks are harder than others. There are a few things that have helped me tremendously to deal with jealousy and envy.
Focus on my friends and relationships. I’ve been incredibly lucky to have a great group of friends that are supportive, fun and smart. Even if I was to have a huge startup exit, these are people I’d still love to spend time with every day. I don’t know that everyone can say the same. Even if they can, I’m still incredibly lucky to enjoy the company of such awesome people every day.
Time freedom. Being able to wake up whenever I want, work out in the middle of the day, play basketball in the evenings and take lunches with friends is really enjoyable, and something most people don’t have the freedom to do. I can take midday walks, work whatever hours I want and still be productive. That is a real gift. Regularly interacting with people outside of tech/startups has also helped me realize how lucky I am to have such freedom with my time.
Career freedom. This might be a heavy bit of rationalization, but in a way not having a massive success is freeing. Success, while awesome (I’m sure), also locks you into things. If you have a successful exit, pressure is greater for your next company. If you’re the founder of a hot startup, the pressure is to improve upon that success. Think how the founders of Twitter feel – millions and millions of users, one of the most popular products in the world, and the startup community is hating on them for lacking a business model. With no success under my belt, I have complete freedom. If Roommatefit doesn’t work out within the next year, I can take time to travel, work with anyone I want, start something new, take on new projects, or work a job and relax for a while. Such freedom of choice shouldn’t be taken for granted.
Focus on the positives. There are so many good things about my life, it’s sometimes hard to appreciate just how good I have it. I’ve found it helpful to focus on things I’m doing well with, and be grateful for what I do have. Am I meeting interesting people who I enjoy spending time with? Am I healthy? Having fun? Learning new things? Taking risks? Building good habits? Asking myself these questions helps put things in perspective and realize I’m on a good path, even if it doesn’t lead to an immediate $1b valuation.
Get mentors. This is critical to dealing with the inevitable feelings of self-doubt, questioning and uncertainty that come with trying to start a company. My personal mentors have helped put things in perspective and keep me sane, while also giving great business advice. This is probably the most helpful thing I’ve found to deal with feelings of envy and doubt.
Focus on the work and not the results. Steven Pressfield uses a great quote in the War of Art: “we have a right to our labor, but not to the fruits of our labor”. This is really, really hard to do. However, I’ve been working to trust the fact that if I work hard and stay on task, good things will happen (this is especially true when writing a book). My focus right now is on building skills and discipline with the projects I’m involved with, and not as much on making tons of money. Or, at least, that’s what I’m shooting for.
Realistically determine what my goals are. Goals are incredibly important. Am I working to craft a life that makes me extremely happy, or working towards doing something massive that has the potential to change the world? At some point, something will have to give. Changing the world isn’t easy, and requires tons of personal sacrifice. This is one of the main things I took away from Steve Job’s biography, just how large a sacrifice he made to do what he did. If I’m working to optimize my happiness, why should I be jealous of someone who’s out to change the world by solving an incredibly difficult problem? They are on a different path that requires a different level of sacrifice and work.
Make a conscious effort to realize other’s successes exist independently of me. This is a hard one, and something I’ve taken from the Last Psychiatrist. As stupid as it sounds to write it out, it can be easy to see other’s successes as a reflection of your failures. Other’s successes exist independently of me. If someone I know sells a company, raises a ton of money or does really well, I had nothing to do with it. That action occurs completely outside of me, and has nothing to do with what I’m doing or working on. It’s the height of narcissism to think otherwise.
Don’t worry about potential or what others think. It can be easy to worry about what others think of you – how things are going, how well you’re doing, etc. I’ve been trying to focus on improving myself and becoming a better human. As one of my mentors put it, what matters more – being seen as high potential, or being a genuine human being people like and want to be with? In the end, even the rich and powerful want the same things: to be liked, have friends and be happy with yourself. Each of those things is accessible, regardless of how successful I am.
Don’t read tech news. Mark Suster has a good post on this. If it doesn’t help you or make you happier, why bother reading it?
Work with people in different situations. I’ve started volunteering as a 6th grade mentor at a low-income school nearby. It’s weird: outside of a startup context, you realize that other people are happy, even though they may not be changing the world or making gobs of money. Even outside of this reality check, it’s good to work on something that concretely helps another person and isn’t focused on making money. It’s helped me realize it’s a privilege to worry, even for a second, that I’m not running a company with the potential to make $100m in revenue. Most people have much larger problems.
Objectively look at the career ladder. It helps to think about how I feel right now (envy, not like a success) and compare that to where I was last year. For me, if you told me two years ago that I’d be running my own company, be in Entrepreneur magazine, had the chance to work with Gabe Weinberg and Noah Kagan, and live in SF for 4 months, I would have told you I’d be ridiculously happy. That’s how I would have defined success two years ago. I am ridiculously happy – but in terms of my career, don’t feel at all different. Instead, I want to sell a company, become an “influencer” and take on even more ambitious projects. My (very) small successes have only opened up a new level of wanting in terms of career achievement.
Practice stoicism. I am constantly trying to remind myself that in the long run, none of this really matters. There are so, so few men who really stand the test of time. And for those that did, what good did it do them? I love this quote from Sebastian Marshall:
That leads me to the final point, which is you gotta remember this is all a circus. Life is really a circus. Are you such a big deal that you can’t be embarrassed, or make a mistake, or do something wrong? No, you’re not. You’re not a big deal. At least, I’m not a big deal. I’ll say some stupid shit at some point, and get embarrassed, and look bad. Oh well. If things break the right way, I’ll also found branches of science, inspire people, build amazing businesses, found charities that actually work, make art, fund art, fund science, build a virtuous international dynasty, and all sorts of other stuff. But if I try and fail? Well, whatever, I’m not such a big deal. I can be embarrassed. It’s okay if I get something wrong or say something stupid. Most of what we obsess over is going to turn to dust anyways.
I hope this is helpful to someone out there. It’s helped me to reflect on the above, and just realize that life is short. In that context, it seems silly to worry about the millions or billions of dollars you don’t have. I’m working on improving myself and putting in the work to do big things. Hopefully, one day, some measure of success will follow. If not, I’m working on being ok with that.
Thanks to Jordan Messina, Nate Speller, Josh Albrecht and Adam Paulisick for reading drafts of this post. Special thanks to Adam, who’s thoughts and advice have helped me think about this issue over the past year.
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