Fighting Founders Depression

It was a beautiful summer day; the sun was shining, the birds were chirping, and here I was, sitting on the back porch, having returned home early from the office. I didn’t have sunshine and rainbows on my mind, far from it — I was devastated about how far I’d fallen. I thought I was a complete failure, worse than worthless, an embarrassment to my family and friends. Surely, when my secret was revealed, everyone would laugh behind my back. My business was running out of money and I had no clue how to save it.


On the surface, I was the envy of my former colleagues. I had recently quit my high-paying sales job after winning accolades for the previous years. I vacated at the top of my game. In actuality, I was always on top — generally #1 or #2 in the company. I excelled at my job, colleagues loved working with me — especially my managers, as they were promoted quickly thanks to my stellar performance. Am I bragging? No, just telling it like it is. I knew how to play the game, through dedication, hard work, and a hyper-competitive drive. Having a successful career made it all the more difficult to walk away from Corporate America. And I use the word “walk” very loosely. It took me six months to mull over the idea of leaving my job before I was finally ready to make the leap. Why leave a job in which it was almost too easy to get paid? The formula was simple: show up, follow directions, and you will eventually have the 401k, white picket fence, and happy life (or so they say). When I walked away from what I considered easy money to take a complete risk, I was anxious, but still completely confident that in the worst-case scenario, I could re-enter corporate America and crush it again in any job. It wasn’t until I went public with my resignation and my phone started ringing, that I realized how crucial this decision would be. I even remember a friend telling me “Congratulations, you are going to be a millionaire one of these days!” That’s when it hit me: my business was going to dominate the world…

…Or so I thought.

For those of you that have yet to take the leap of faith, starting a business goes like this:

You work every night and weekend for months, sometimes years, on your Great Idea while still collecting a paycheck from “The Man.” Eventually, this Great Idea consumes you day and night, so it’s all you think about. You become obsessed over your Great Idea, jealously devoting all your time to it. Eventually, you say “screw The Man!” You take the risk, moving away from the path most traveled and jump off the cliff so you can be monogamous with your idea. From there, you have no one to answer to and enjoy complete anonymity to make mistakes. Your friends and family envy you, your life, and your confidence. Why? Because you are doing what they wish they had the guts to do. You are building a business, a Life. You put in the hours, working on tons of tasks that will grow that great idea into a great business. Of course, this doesn’t require just your time, but your personal savings. You build a team, paying others for services to help make your great idea become even greater. Your expectations were high. Why isn’t your business the success story you knew it would be? (Hint, it doesn’t happen overnight). Pretty soon, you lose focus and momentum. At first, you tell yourself you need a break, a lull… you get sucked into sleeping late, watching TV during the day, or spending more time on social media. You kick yourself back into gear and go hard at the business again. Maybe you raise money, maybe you boot strap it — but eventually you pour more of your own money into the business. It’s the old saga of peaks and plateaus, until eventually all you see are mostly plateaus. Potential customers say they like what you built, but it’s just not the right time to make a purchase decision yet. You pour more money and emotional capital into your business. Peaks and plateaus turn into plateaus and valleys. When you made that leap from your job and jumped over the cliff, you never knew how far down the valley could go.

This happens a few more cycles until ultimately, you land on your back porch thinking you’re a failure.

Having a “back porch” moment is a given. Your former coworkers back in corporate America wont get it, your spouse won’t understand, and your friends certainly won’t know the feeling; but trust me on this: other entrepreneurs get it. If another entrepreneur tells you they never had a “back porch” moment, then they are lying to your face or being a self-righteous asshole. In either case, you must avoid them completely. EVERY entrepreneur that I’ve spoken to off the record has admitted having experienced this moment. YOU ARE NOT ALONE. Grown men have cried in my office, telling me that they felt lost. Some of my entrepreneurial cohorts speak with therapists weekly, and even the famous investor Brad Feld has admitted he had thoughts of suicide. Can you imagine what Mr. Feld’s back porch moment looked like? The steps were cracked, splintered… the porch light bulb broken… Every entrepreneur has a back porch moment. Again, YOU ARE NOT ALONE!

I speak from personal experience on this subject. The porch behind my house is a dark place. There’s a well-worn seat always at the ready for me to sit my weary ass down. Of course, reading this will not cure your sorrows completely. Just trust me. I’ve had many moments where my back was against the wall. Where I had to grit my teeth and give my all, it was an absolute grind. I’ve identified 4 ways that may help you escape the depressing phases of starting a business.

Talk to someone experienced:

Choose someone that has experience with startups. This can either be a mentor, investor, or even a therapist. They will know where you’re coming from, and share their own back porch moments and how they got back to work. On a personal note, when I was going through my lowest point, I had no one. I didn’t realize how common it was, and consequently felt completely isolated. Refusing to share my low points with someone more experienced prolonged the recovery period. Hindsight is 20–20, and for me this first point is the most important. Fortunately, relying on the next three points helped me.

Take Action: visit a meet up and talk to more people, visit a co work office and make new friends, or even reach out to me… I know what you are going through and I can help you get out of it.

Choose a simple goal that has a deadline:

The activities of an entrepreneur often never have closure, so it’s hard for us to measure success. Instead of waking up every morning saying, “I’m going to grow my business” and then not having any clue where to start and feeling helpless to make that happen, say “I’m going to post 2 new blog posts” or “I’m going to call 15 prospects.” By setting clear goals, you can measure the day’s success whether you’ve achieved your daily goal or not. You need small wins. These wins will help you feel better and build the muscle memory for what got you there in the first place: hard work. What I used to do was break my day into simple and manageable goals that I set each night before I went to bed. Don’t leave your goal setting for the following morning. Why? Because far too often we wake up and get distracted by the BS of emails and tasks that may seem like they are urgent but are instead far from priority.

Take Action: Set your priority goal the night before and then chop away at them through the following day. Celebrate these small wins.

Get sweaty:

This is so helpful. Sometimes, you just need to get a little frustration out. I’m not talking about going to the gym 3x a week (though that is very helpful and creates a schedule and routine), but do something either fun with friends or challenging on your own. I started by running a couple 5ks with family; then did a Tough Mudder, and eventually “graduated” to triathlons and ultimately the granddaddy of them all the Ironman. I needed to keep feeling like I could push myself past any limitation because that is really what is needed to get your business off the ground.

Take Action: You can start your physical activity goals small; the important thing is to sweat it out!

Take frequent and small breaks:

No, don’t just sit your ass on the couch or play on social media. I mean literally shut it down. Walk away from your environment and go. Travel outside of your local area, maybe visit some friends, or see a new place. I recall traveling out of the country with some friends at one point; it was so helpful to forget about how I felt at home especially when I thought I wasn’t able to move the needle with my business. After a few drinks at a bar we visited, I remember a friend confiding in me that he was envious that I had the courage to walk away from corporate America and start a business. He wanted to do the same but he said, “I’m not like you.” He thought he could never do it. Hearing something like that from a friend that I respected was tremendously motivating.

Take Action: It’s important to stay in touch with family and friends and continue participating in hobbies. Do what makes you enjoy life. These breaks can be rejuvenating and bring fresh enthusiasm and creativity to your growing business.

And when all else fails, remember this truth:

Entrepreneurship is living a few years of your life like most people won’t so that you can spend the rest of your life like most people can’t.

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