How can humility save the entrepreneur? One expert has the answer

General Assembly


Michael Dermer, founder of The Lonely Entrepreneur.

There’s a crushing, isolating pressure that engulfs many entrepreneurs as they try to transform a passion into a profession. Long days extend into exhausting late nights as they wrangle talent, negotiate funds, and wonder just how far away success (or failure) lies.

In the world of business, anything can happen and nothing is promised. No one knows this better than Michael Dermer, a lawyer, author, and life and career coach, who painstakingly built a company over 10 years only to see it collapse in 10 days during the financial crisis. Undaunted, Dermer turned the hard lessons he learned into an opportunity, launching a platform to help people start businesses with the support and knowledge they need.

The Lonely Entrepreneur — a book, website, and global community — is Dermer’s salve for the heartaches of entrepreneurship. Packed with learning modules, community connections, and expert advice, The Lonely Entrepreneur helps budding businesspeople get on their feet and take strides toward success.

We tapped Dermer for his top tips and reflections on the entrepreneurial experience.

What is lonely about being an entrepreneur?

Entrepreneurism is such a strange endeavor. I don’t think there’s anything else in life where you’re asked to do and think about so many different things at the same time. Even if you know bits and pieces of it, you have this overwhelming feeling that you really have to figure it all out because you’re the one who’s guiding the ship. So, it’s definitely not a physical loneliness — although that happens at times. It’s more about what it’s like to sit in the entrepreneur’s shoes, the feeling that you’re the one responsible for figuring it all out.

What mindsets or practices can people develop to help stave off the loneliness?

We’ve done a disservice to entrepreneurs because we’ve said, “As long as you have passion and grit you’ve got enough to succeed.” Yes, something has to inspire you. But we can all have ideas. How do we prepare people with ideas to be better entrepreneurs so they have a better chance of bringing those visions to life?

First and foremost, people need context on what business actually is. It’s a vision, a financial plan, an operating plan, and people. These are the ingredients that go into that soufflĂ©.

Second is understanding and acknowledging what you know and don’t know, and what it is that you’re good and not good at. It doesn’t weigh people down to do things that they love to do. A coder will code all night long. They don’t care. They love it. It’s when they’re asked to do finances that it changes. That’s one area that makes you feel like you’re drowning in quicksand.

An entrepreneur has to be humble and a learner.

It’s often challenging for people to identify their weak points and seek help. How can an entrepreneur overcome that reluctance?

An entrepreneur has to be humble and a learner. (I would be completely lying to you if I told you that I — being a college athlete, a lawyer, and a boy — was any of those things when I was running my business.) You have to embrace the notion that if you want to unlock your entrepreneurial spirit now and in the future, you have to get better at it. There’s a humility that comes with the fact that yes, I’m self-assured about my idea but it makes me actually better at being an entrepreneur by recognizing and embracing what I don’t know.

What are some common hurdles an entrepreneur can anticipate, and possibly prepare for?

Well, there’s the people part. It can be really difficult, especially in the early stages when you’re not paying full compensation or can’t afford to pay everyone, or you’re working with team members who are only part-time. To manage and organize that can be really frustrating. You’ll have an advisor that’s like, “OK. I’d be happy to give you five hours a month of my time,” and then you’ll send a hundred-page business plan and get pissed off when they don’t read it.

Then, there are the investors. You could go into two different investor meetings in the same building an hour apart and one will say your idea is not different enough and the next one will say your idea is too different. They’re poking and prodding your baby: Why did you choose that pricing model? Why did you do that branding? And that’s hard.

Ultimately, you’ve got to be steadfast in your belief of your idea, and have it thought through. You have to be prepared for the fact that there are going to be people who will be doubtful and question you. And, again, it goes to that humility of being a learner and how you get better at it, as opposed to being defensive.


Michael Dermer’s book, The Lonely Entrepreneur

What advice do you have for entrepreneurs when they face failure? What happens the day after a big loss?

Well, I’m not so proud to say I have a little experience with that. After we built our business up for 10 years, it got destroyed overnight by the financial crisis. Based on that, here’s what I would say. You have to figure out a way to not focus your energy on the emotion or the implications of it and just do the work. In the movie Apollo 13, when the spacecraft is coming back into the earth’s atmosphere, one of the characters turns to Tom Hanks’ character and asks, “What happens if this happens and this happens and this happens?” Tom Hanks gives a great answer. He says, “We need to get 143 things right. We’re on No. 7. Work the problem.”

So, when your best employee quits or your biggest customer leaves, you can’t just say, “I wonder if I’m cut out to be an entrepreneur?” You’ve got to just work the problem. Don’t spend your time on the energy and the emotion of “What if it goes wrong?” Spend your time on chipping away at the problem. Then, you’re making progress because you’re reducing your chances of everything going wrong.

Can you recommend some ways an entrepreneur can find balance and perspective on their lonely road?

Number one is sleeping. When people would tell me to sleep more, I would give the typical answer of “I don’t have time to sleep, my business is collapsing,” blah, blah, blah. Then one day, by mistake, I fell asleep on my couch in my office for a half hour at like four in the afternoon, and I felt so much better. I could work later. So, one needs to sleep. Crash for a half hour a day in the middle of the day, and one day a week, get eight hours. It’s amazing what it will do for you.

Secondly, you’ve got to have your releases. They can be anything — going to the gym, yoga. For me it was little things, like seeing my little niece and nephew because they don’t really care about your pricing model that month.

The last thing is, when you do take the time to do something away from work — a dinner party, a birthday party, you go out to dinner — be there. If you’re not going to let your mind be there, don’t go. Sit at your desk and work. Because again, it comes down to being a better entrepreneur. Part of you getting better at it is giving your mind a little bit of space to breathe and to not think about work all the time.

— By Rebecca Louie

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