10 Things That Keep Entrepreneurs Up At Night


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What keeps you up at night? Everyone has something they worry about, and it’s usually at night when those concerns bubble to the surface. How do you control your thoughts and stress at night so you can get the sleep you need?

To help you manage your worries, we asked business leaders and entrepreneurs this question for their input. From balancing work and family to thinking about keeping employees motivated, there are several concerns and solutions that may help you settle down at night for a more restful slumber. 

Here are 10 things that keep these professionals up at night: 

  • Balancing Work and Family
  • Concern for My Employees
  • My Never Ending To-Do List
  • The Traffic Jam of Business Development
  • Making a Client Faux Pas
  • The Need to Keep Employees Motivated
  • Finding New Patterns of Growth
  • Worries About the Future
  • Managing Unfounded Doubts
  • Excitement for the Upcoming Day

In all seriousness, my three young children keep me up at night as an entrepreneur. Kids cry. They’re scared of the dark. The list of nightly interruptions goes on. Balancing entrepreneurship and family life is challenging, and if you’re not careful, it can be very exhausting. To help overcome this challenge, I leave my computer at work when I go home for the night. By leaving work at work, I’m able to fully focus on my children when I go home. I’ve found that kids — just like clients and employees — need attention. Committing to providing that attention in both environments is the key to getting some good rest at night.

Brett Farmiloe, Markitors

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Concern for My Employees

As an entrepreneur running two businesses, stress can get pretty high. One of my businesses teaches stress reduction, so I “practice what I preach” and meditate often. However, on the nights that I lie awake, I worry about my employees and interns (if they have expressed disappointment or discontent). That is when I take a few deep breaths, do a body scan, and go back to sleep!

Beryl Krinsky, B.Komplete

My Never-Ending To-Do List

My never-ending to-do list is what keeps me up at night because it literally never ends. I know it’s part of running a new business and that it’ll get better over time. But for now, there’s always something on my mind that I need to finish, someone I forgot to respond to, an important email that I need to answer, a new blog post or course that I want to write, or new content I want to create for my socials. I can’t wait to get to the point where I can rely on my business growth a little more without needing to be so active all the time. And at the same time, I really enjoy running my own business and feeling busy all the time.

Angie Makljenovic, She Can Blog

The Traffic Jam of Business Development

My mind races like a massive rush-hour traffic snarl on an interstate freeway, and it’s all over a dirty (and yet exciting) two-word phrase: business development. As the owner of a small, lean strategic consultancy, our client lead times range in the “months to years” category. It’s a slow burn. I met someone at a conference. I sent them a holiday card. I nurture them through relevant emails and sharing news articles. I send a proposal as they begin the budgeting cycle. We wait until their new fiscal year starts. They require board approval — the entire process takes a very long time. And as such, filling the pipeline is always balanced with contracting and fulfilling one-off consulting clients, recurring revenue and retainer clients, and keeping that mix balanced just right so that my team and I have a constant and consistent source of revenue while being able to do the work, and keep new work coming — one foot on the gas, one on the brakes at all times.

Josh Yeager, Bright Brothers Strategy Group

Making a Client Faux Pas

When I make a cringe-worthy mistake while interacting with a client during the day, I’ll hardly get any sleep that night. The interaction will continue to play on a loop in my mind as I agonize over all the things I should have or could have done. I’ll feel a bit embarrassed and frustrated for a while until I talk myself down and convince myself the situation was not as bad as I made it seem.

Sai Blackbyrn, Coach Foundation

The Need to Keep Employees Motivated

The constant thing that keeps me up as an entrepreneur is ensuring that my employees feel motivated. As entrepreneurs, we, by default, have the most passion and investment (both mentally and emotionally) within the company. Therefore, the challenge is to create a similar level of motivation within everyone. Over time, I have found that motivation can come from various sources, but by and large, it stems from feeling valued and appreciated. If I can put the needs, wants, and well-being of my employees before myself, success will follow.

David Wolfe, Olivers Apparel

Finding New Patterns of Growth

Growth — and always doing better are on my mind. I am most creative at night, so it’s really a time for me to think about the company, the team, and how we can iterate and innovate. Keeping ahead of customers’ needs is vital. I like to strategize for each coming day so that we stay ahead and stay organized.

Marc Atiyeh, Pawp

Worries About the Future

The one thing that keeps me up at night is worrying about the future. Entrepreneurship can be an anxious path to walk. You are worried about the success of your business and if you made the right decision for the future. It can be hard to tune these thoughts out when you’ve put your heart and soul into this venture.

Chris Cronin, KITANICA

Managing Unfounded Doubts

For me, it’s managing the unfounded doubts about potential success and failure when taking risks. The night is usually the time I recognize any habits, recurring thought patterns, or items in my life — good or not so good. Overall, I still get a great night’s sleep, but I owe that to the company’s great ability to know who is best placed to solve a problem or make a decision and to let go of concern over the issue, knowing it’s in capable hands. Since everyone at our company is close, it helps to share the problem or stress load between all of us.

Daniel Kane, Ridge Wallet

Excitement for the Upcoming Day

It’s true — being an entrepreneur is exciting! While you’re able to make your own decisions, build your company’s brand, and even set your own schedule, you can’t control when those ideas keep you up at night. Many entrepreneurs seem to have a little trouble “calming” down for the night and trying to leave strategies and campaigns until morning. But in the end, it’s all totally worth it!

Lauren Kleinman, The Quality Edit

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