10 Ways to Manage the Intensity of Starting a Company

My senior year of college I took an impromptu road trip from LA to Barona Casino near San Diego with four friends. I played 15 hours of black jack and turned $100 into $1,500. My friends were comped surf and turf lunches. As we ate, they agreed that I could see the matrix. Between the dining hall and the exit, it took me less than 20 minutes to lose all $1,500. Back in LA that evening we visited a street carnival, and I rode a ride called The Zipper. A friend who wisely watched us from the ground counted 20 consecutive cage rolls (the impressive work of a skilled ride operator). I made it two steps off the ride before vomiting. I was too sick to join my friends later that night, so I curled up on the couch to watch Jurassic Park on NBC. I reflected that in the past 24 hours I had won $1,500, won surf and turf meals for my friends, lost the $1,500 and then lost the surf and turf. Surprisingly, I felt zero regret. Instead, I felt acutely alive. And I didn’t know it at the time, but this experience foreshadowed my later career as an entrepreneur — a career that I’ve treasured thus far. Starting a company is an intense experience, and intensity is an exciting qualification. That said, the endeavor charges two tolls: firstly, the up and down nature begets emotions that can boil over into other aspects of your life, and secondly, obsession with your company can throw the rest of your life out of balance. Particularly for the positive thinking founder who’s crazy enough to start a company, it’s easy to foresee the pros of doing so. It’s not as easy to foresee the cons. I’d like to share the two biggest psychological traps associated with starting a company that I’ve experienced, and to share how I navigate them.

The Roller Coaster Problem

A startup is nothing if not a roller coaster of emotion. Within the same week, you will swing from 100% clarity that your company will soon be worth a billion dollars to 100% clarity that your company will soon be bankrupt. You will close a customer who triples your revenue, you will nail your quarter, you will see competitors raise ungodly sums of money, you will miss your quarter. Such a pressure-packed environment of constant highs and lows can become addicting, and these feelings of euphoria and despair can bleed into other aspects of your life. Successful people in high pressure careers possess an ability to regulate their emotions amidst tumult, and to compartmentalize. Athletes. Surgeons. Attorneys. The list goes on. As an entrepreneur you must learn to maintain a consistency of demeanor for the good of yourself, your family, your team, your customers, your investors and your vendors. If you act on every feeling of exhilaration or terror you will burn yourself out, and you will burn your team out. I call this the roller coaster problem. And it’s a big one.

The Abyss Problem

Particularly in the early stages, entrepreneurs fly at many altitudes: product, engineering, operations, sales, marketing, fundraising, investor relations, PR, administration, HR, business development, strategy, etc. There’s much to consider, and switching from one altitude to another is taxing. From a geometric perspective, you must travel the hypotenuse (the longest edge of the triangle) to get from one task to the next. Along the way, it’s easy to get sucked into a headspace in which you’re constantly thinking about your company. This type of obsession creates problems. Firstly, relationships with family and friends will suffer because you won’t be emotionally present when you’re with them. Therefore, even though you’ll be learning a lot, in a more holistic and real way you will become a much lamer version of yourself. And no one wants to be lame. Secondly, your company will suffer because you will lose the perspective and clarity of thought that you get from not thinking about your company, and you need this clarity to make even the simplest of decisions. Thirdly, you will burn yourself out and your team out. Unfortunately, the public nature of startup success or failure amplifies this challenge. The first thing many people will ask you is “how’s the company doing?”, and this puts you at risk of having the company become your identity (and you’re cooler than that). This is the abyss problem. It’s a big one too. Here are ten ways to manage these problems.

Practice Compartmentalization

It’s important to acknowledge and understand your emotions. It’s not always important to act on them. Practice being in touch with how you’re feeling, and why, and not acting on those feelings. Don’t get me wrong, it’s healthy to celebrate when things go well or curse when things go poorly. But you should have the ability to forget the last pitch and focus on the next one when the game is on the line.

Slow. Your. Roll.

Do all of your good ideas come in the morning? Do you get at least a couple stupefied looks from coworkers per day? You might be thinking and processing information too quickly. Take the time you need to center yourself during the day. Take a ten minute walk. Take 20 deep breaths. Use a meditation app. Calming and centering your mind is as important as a good night’s rest in allowing clarity of thought. And you need rest to be at your best.

Sometimes Any Decision is a Good Decision

Being an entrepreneur isn’t about making the right decisions as much as it is about learning from the wrong decisions. Decision fatigue is real, so don’t sweat the small stuff. Sometimes you don’t even need to sweat the big stuff. As long as you’ve analyzed a situation with all of the hard data and soft anecdotal indicators at your disposal, make a call and move on. The faster you make a decision, the faster your team will move on to the next challenge (if you were right) or diagnose the misstep (if you were wrong).

Don’t Talk About Fight Club

Outside of work, people will associate you to your company, and more often than not they will ask you how work is going. My recommendation: answer briefly, and then quickly and sincerely change the subject to their work, or to something else entirely (“can you believe what the POTUS just tweeted!?”). You don’t want to get sucked into thinking about your company when you don’t need to be, and you don’t want your company to become your identity. Time away from your company is precious, and you want to gain every ounce of perspective you can from it.

Delegate

One of my biggest mistakes to date at TRED has been not delegating responsibility quickly enough. Delegating is tough, because trusting a person in an important role requires that you know that role well enough to hire for it — which likely means that you’ve performed that role yourself for some period of time. Yet, it’s extremely difficult to manage more than two or three roles by yourself effectively. Start looking for people you can grow into leaders as early as possible, and trust them!

Prioritize Stress Relieving Activities

Are you an endorphin junky? Or a painter? Do you play the piano? Whatever your jam, don’t stop jamming. In fact, now that you’ve started a company you should be jamming more than ever. These activities clear your mind. So put them on the calendar and make them a priority.

Travel

Few things bring perspective as quickly and richly as travel. I can’t count how many times I’ve been hesitant to take a weekend away, only to return with easy answers to dilemmas that I’d burned a flotilla of brain cells struggling through previously. The more frequently you get out of the office, the more frequently you’ll return to the office with perspective and clarity of thought. Added bonus: you can consider your time away as a test to see what breaks when you’re not around, so that you can fix potential problems before they grow.

Lean on Professional Peers and Mentors

Founding a company and managing people is extremely lonely — even if you have co-founders. Very few people can relate to your daily work challenges and it can be inappropriate or awkward to consistently confide in employees. To this end, it’s important to develop relationships with professional peers that you can lean on for support. Find a group of startup founders at other companies and hang out with them regularly for dinner, beers or coffee. Outside of your company, these are the few people with whom you should regularly discuss work. Resist the urge to get into bragging contests about your milestones and successes with these friends. Instead, share your problems and listen to their advice. Try to get them to share their problems and try to provide perspective. This is terrific therapy. Mentors are important as well. Just as it’s important to have a terrific board to help you gain perspective on the right direction for your company, it’s important to have terrific mentors who can help you gain perspective on the right direction for your career and personal life. This is important stuff to get right.

Share the Company’s Problems with the Team

As a leader, it was a natural instinct for me to shelter my team from bad news and setbacks. Unfortunately, doing so is a terrible mistake, and creates new problems. Firstly, that “weight of the world on your shoulders” stress won’t abate. Secondly, you will miss out on all of the terrific solutions your team has to offer. Thirdly, your team will miss out on the sense of empowerment and trust you provide them with when you genuinely ask them for help. Fourthly, if you’re as bad an actor as I am, the team will know something is up regardless. Communicate. Ask for help. Don’t be surprised how much more powerful 15 brains are than one.

Strengthen Personal Relationships (duh)

Needless to say, it’s important to spend as much time as possible with your loved ones. Outside of the office, these are the people who inspire you to be who you are, and the last thing you want to do is forget that fact. Avoid talking about work too much with these people.

Starting a company is the trip of all trips. You get to take a clean shot at creating the future. You get to roam a land in which work doesn’t feel like work. If you can find ways to manage the psychological highs and lows, to avoid becoming obsessed with your company, and to avoid letting work stress bleed into the rest of your life, you will be much more likely to succeed with the product and team that you create. You’ll also be a happier, healthier, more well rounded person! In fact, starting a company is similar in emotional intensity to falling in love. Meaning makes life worth living, and it’s intoxicating to be swept up in the intensity of a meaningful new connection. But to develop a sustainable marriage you must be able to see the forest from the trees. Hopefully these ten ideas help! :)