What Keeps an Entrepreneur Up at Night?

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Before I dive into the many topics that keep an entrepreneur up at night, I’d like to thank Matt Barry for suggesting this column topic in this past November. I love interacting with my community of readers and am always happy when I have the opportunity to address one of their questions. Feel free to send any questions to Connor@ConnorGillivan.com.

As I was brainstorming what to write for this column, I started to flashback to the many nights I found myself staring at the ceiling unable to fall asleep.

Something was on my mind. Or maybe too much was on my mind. For whatever reason, my mind was running at a pace much faster than it should be for 1:00 am at night.

Each night, the something would be a little different, but the most surprising thing may be that the something was not always a bad thing. In fact, some nights I was left restless and unable to fall asleep because of the positive, exciting things that were stuck on my  mind.

What Keeps an Entrepreneur Up At Night?

While I will admit that the negative thoughts definitely led to a worse night of sleep, I have spend my good share of nights staring at the ceiling wondering when I would ever fall asleep because of the dream future I was transfixed on.


What has kept me up at night has closely coincided with the stage of the company I was working on over the past 5 years that I have been a full time entrepreneur. When the company was up, I was usually up thinking about how we could continue to grow. When the company was down, I was usually awake trying to forget about what had happened in the past 24 hours. And when everything seemed to be going right, it was then that I would sleep like a baby.

The seven examples that I’ll present are very specific to my experience as an entrepreneur, but the headlines will give you a good idea of what worries most entrepreneurs deep into the night.

Reason #1: A Difficult Problem to Solve

Portlight was starting to work with more suppliers and we needed a universal pricing equation that would take in a handful of known and unknown factors. The goal was to spit out a set of prices that would  allow us to achieve our desired gross profit for every product in our inventory.

I was tasked with creating the equations and I spent days working to figure it out. In the week or so that it took me to finally solve the problem, I was kept up at night by strings of numbers, formulas, and mathematical equations racing through my head.

For most entrepreneurs, there is always a problem to solve. When we can’t solve it or we are in the process, it tends to consume our entire being.

Reason #2: Mistakes in Operations

Portlight has just reached over 200,000 products in our active inventory being sold on Amazon.com and we needed a new way to manage and reprice our products to stay as competitive as possible.

After weeks of research, we finally decided to license a repricer software that was customized for the Amazon Marketplace. On the day that we decided to integrate all of our inventory, something went drastically wrong screwing with all of our pricing on Amazon.

Let’s just say that sales took a small hit.

Making mistakes and learning from them is an everyday happening for entrepreneurs, but some can be a bit more harsh than others.

Reason #3: Personnel Management

Just when you think everything is going according to plan, you’re thrown a curve ball by someone on your team. One of the most nerve wracking situations that has occurred multiple times throughout my career as an entrepreneur is hearing that one of your best workers is deciding to leave the company.

You had spent months if not yeras working with them on building the company fostering a strong friendship as you went through the ups and downs of running a business. Getting that news after lunch on a Tuesday makes sleeping for the remainder of the week quite a chore.

Being an entrepreneur also means that you are eventually the leader and soundboard for the people that you hire. When Portlight grew to over 20 team members, there were certain weeks when it seemed like everyone had something going on in their personal lives.

You do your best to hear everyone and make the right decisions, but it can keep you up at night wondering what their reactions will be.

Reason #4: A Never Ending To Do List

It’s now 2016 and I am in the process of starting two new companies while juggling my passion for writing and running Portlight. My to do list for both startups is endless and will continue to be for the next year until first key hires are made and the systems and processes are completely ironed out.

When you’re being pulled in so many directions and working on the beginning of a new business, you can spend hours laying in bed thinking about how it’s all going to get done. However, you can also lay there dreaming about what life will be like once all of the heard work is complete.

Reason #5: Financial Woes

Portlight’s revenues had been cut out from under us by Amazon as they made policy changes and inspected our seller account. As we appealed the hold on our selling abilities and awaited a response, we were obligated to continue paying our operating expenses, i.e. payroll, office, technology, etc.

All entrepreneurs worry about finances at one time or another in their career and it can place a heavy weight on your shoulders as you await the results. Cash is king while starting and growing a business from the ground up.

Reason #6: Firing and Layoffs

We made the grueling decision that we had to make a first round of layoffs after attempting to hold out on a decision from Amazon. It was the last thing that any of us wanted to do, but we had to follow through in order to avoid financial burden for the company, ourselves, and our team.

As I lay in bed thinking about laying off close to 20 people on the next day when I woke up, there was an inescapable knot in my stomach that kept me up late into the night.

Making the decision to fire team members is a gut wrenching action that does not get easier with time and practice. I’d confidently state that most entrepreneurs would say the same.

Reason #7: Pure Adrenaline from an Awesome Day

From time to time, there are those days that happen out of the blue that leave you with enough energy to work another 12 hours or sprint a 5k. As an entrepreneur, I live for these days.

An amazing hire accepts the offer. You hit a record setting level of revenue. You solved a problem that has been stumping everyone for the past month. You meet and connect with an amazing new person. The list goes on.

The life of an entrepreneur is characterized by the highest of highs and the lowest of lows. You live to take risks and the results through you one of two ways: down into the ditches or up into the skies. While both results may steal hours of sleep from your daily routine, it’s all worth it in the end.


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About Connor Gillivan

In the past 10 years, I’ve started 7 businesses & built two to $10M+ in annual revenue, teams of 30+ & an exit in 2019. Today, I run SEO & growth for my 4 B2B companies while teaching millions how to make SEO simple.

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Article Comments

  1. Gretta Mccaskey

    March 1, 2016 4:17 am Reply

    I am curious to find out what blog system you’re working with? I’m experiencing some minor security issues with my latest blog and I would like to find something more safe. Do you have any suggestions?

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