small dogs / big dogs

Avoiding Depression While Not Running a $1B Company

Instagram sells for $1B. Evernote is now valued at $1B. Pinterest at $1.5B. 3 month old companies coming out of YCombinator are getting investments based on $10M+ valuations. And today will be the Facebook IPO which will likely put a market cap on the company north of $100B.

This is not a post about bubbles, it’s a post about maintaining perspective when you are no where close to being one of these companies and never will.

As the founder of a small company in Chicago who only took $17k from YCombinator 6 years ago (YC-W06) and now runs a classic “lifestyle” business that support myself and a small team from client revenues, I find myself wavering between being fairly satisfied with the state of my business life to mild depression and jealousy that I’m not in a situation to be cashing in myself.

Regardless, I still have a lot of passion and belief in my business and won’t be leaving it any time soon. Our growth path has been slow and steady, not meteoric. In the face of an ever frothy investment and acquisition environment, the need for emotional discipline as a small business owner who will never be the next tech or investment community darling is critical.

Assuming many others are in this same position or will be in the coming months/years, here is what I’ve learned over time to keep myself optimistic and psychologically healthy (my wife would beg to differ :)

Spend time with friends who are not in tech or startups
I didn’t realize how important this was until I actually made an effort to spend time with people who work in insurance, are lawyers, or work at non-profits. It’s refreshing to hear about someone else’s work life, realize that the latest .ly startup who claim they will be ”changing the world” still has complete irrelevance to most people’s lives, and even finds my business interesting and exotic.

Read the newspaper
I read the Chicago Tribune, The New York Times, and numerous political blogs religiously every day for one simple reason. They give me perspective that beyond the screen, there is a messy world out there of happiness, scorn, betrayal, heartbreak, victory, life, and death that has absolutely nothing to do with technology.

Go for a lot of walks
I walk our dog at least once a day and often twice. Walks are a great way to clear your head and gain a sense of optimism by the time you get home. I mix up my walk between residential streets and streets filled with small businesses. Every day I walk by those businesses I see the owners toiling away: organizing shelves, working the fryer, wiping counters. I am even on speaking terms now with a few of them. Camaraderie. Those guys are in the same boat I am.

Go visit some of your customers in person
Surprise, surprise, even in your little business there are customers or users who care about your product and have spent time (and hopefully money) on it which means they have opinions about it. They can tell you what they like and don’t like, tell you how it’s benefited them in some way. You’re not doing this just to plan new features. Spending time with these people will make you feel relevant and needed which is critical to maintaining the drive to keep pushing forward.

Maintain a healthy relationship with parents
The great thing about parents is they’ve known you all your life. Hopefully they’re proud of you no matter what and they often have a knack for being able to put things in perspective and not let your head get too small or big. If parents aren’t around, maybe another family member can play the same role.

Keep a journal (not a blog)
So much of what we write these days is for others. We are constantly worried about how we are perceived, whether it’s a FB post, tweet, or blog post for our companies. A private journal is a place where you can be brutally honest with yourself and get everything out of your head. When I’ve been at more extreme points of depression, I’ve realized it’s because I’ve been obsessing over one or two things for more than a day. Writing it down in my own voice with my own insecurities included that I would never tell anyone else about is a huge release.

Find a therapist, life coach, or mentor
I can’t recommend this enough. You need someone in your life who has seen your situation a hundred times before and can share with you lessons learned. More importantly, you need to go through the process of knowing yourself and learning what your trigger points are for your full range of emotions: happy, depressed, lonely, fulfilled. If you don’t know yourself, you’ll never find the stability you need to carry yourself. And this person can’t be emotionally invested in you, like a husband or wife or close friend. They’re too biased to tell you what you may need to hear.

Appreciate your time more
Here’s when I feel best about my business life: when I take vacation whenever I want, when I take naps almost every day, when I go in to our office for half days, or when I look at my calendar and realize I have complete flexibility with my schedule. I answer to no one. Value this rarity immensely.

I hope these techniques are helpful to all the 10 or less employee, 500 sq ft office space (or home office), bootstrapping, revenue-based business founders. It would be great to have millions to buy lots of stuff, live more lavishly, even donate more. But if you constantly dwell on what you don’t have, your life is passing by far too quickly and that’s no one’s fault but your own.

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