Dealing with Lonely Entrepreneurship

Entrepreneurship is lonely.

That statement, short and hardly sweet, is probably the single most common characteristic I have seen to any type of venture: independent consultant, small business (a.k.a. lifestyle business) founder / owner, startup creator, growing business CEO, and even large company owner. In the last few days alone, I counselled an entrepreneur who mentioned how  who mentioned to me how it was full of loneliness.

If you are challenged by loneliness, if you must have a high social content for validation and support - which is not a weakness, just a different personality, one very well suited to most high-achieving salespeople I know - then you either need to avoid entrepreneurship, or find ways to manage it.

• Most initial sales will end an a "no", until you find the right product/market fit along with the right mix of pricing, promotion, placement, packaging, and everything else that goes with it. Getting a "no" makes one respond emotionally with feelings of rejection (after all, "no" is a rejection), one people want to minimize. If you are not prepared for those emotions, you will either be discouraged by them or, even worse, try to satisfy the potential customer by compromising on key goals, which feels great in the short-run but significantly impacts the company's long-run viability. I had a client recently who needed to make every sale, for the same psychological reasons, and so made such compromises, promising to do whatever the client wanted and consistently negotiating herself down on price. It was great for the short-run, terrible for the long-run, and put the financial, delivery, engineering, operations and customer support teams under terrible stress.
• Most investors will not get your idea and say "no." With investors, there is little you can do to change their mind, but they are looking at your whole vision and self, not a single product purchase; the emotional impact can be far greater.
• Even in regular day-to-day, small successes and small failures will feel magnified, leading to irrational and ultimately poor decisions. You need your head screwed on straight to deal with these stresses.

Dan Shipper, 20-something founder of Firefly, posted a great article on why running a startup is like a roller coaster ride, relying quite a bit on Nassim Taleb's fooled by randomness. His post is worth reading, even more so Taleb's "Fooled by Randomness." The key takeaway, though, is that humans magnify every reading; it is the way we are wired. So if you check the status of your portfolio (or company's sales) once a day, the impact will be felt daily, with the negative emotional impact outweighing the positive. If you have 300 slightly down days and 65 5x good days, leading to a net positive over the year, you will feel great if you check once a year, and awful at the end of the year if you check daily.

And yet, as a company founder or executive, you do not have the luxury of checking key metrics once a year or once a quarter. You need to be on top of the metrics so that you can know how you company is doing and make corrections or even major pivots, when necessary.

How do you counter balance the loneliness and emotional reactions that can throw you off, leading to poor emotional state, bad decisions and danger to your health, wealth and company?

1. Be aware: Always be aware that your emotional reactions are magnified. Feel great? Enjoy it. Then take a break - a movie, a book, a sport game, a date - before making any decisions. Feel terrible? Do the same.
2. Have family support: Make sure you have support in the home. It can be a parent, an adult son/daughter, especially a significant other. However, make absolutely sure they understand their role, to support you and counterbalance the extremes. At the same time, understand their situation: they are emotionally vested in the venture, almost as much as you are. Which leads to:
3. Have professional advisors: These can be someone on a formal Board of Advisors, a mentor (we used to call them "rabbi" on Wall Street, ironic since none of mine was ever Jewish), a consultant. The key is that this portion should be supportive of you, have a good analytical head, and, most important of all, not be emotionally vested in the venture. Your advisor needs to be able to know the facts on the ground in your company and market, know you and your personality, and be able to give unvarnished feedback and advice.

Entrepreneurship means loneliness. Loneliness means emotional swings.Emotional swings lead to poor decisions. They can be counter-balanced and managed with the right structure.