8 New Challenges I Faced After Selling My Company

Gary Nealon
9 min readJul 30, 2021

So you’ve sold your company. Now what? While there are plenty of articles out there on what happens, practically speaking, following the sale of a company, it’s hard to find an honest account of what takes place mentally.

As an entrepreneur who sold my own company three years ago, I can honestly say that selling a company is a rollercoaster ride. There’s a great deal of pressure that’s involved when you’re growing a company. And when selling one, it’s all you live, breathe, and sleep. But suddenly you’ve signed the documents and walked out that door, and there’s a huge void that’s left in your life. An overwhelming sense that your life’s about to change drastically from what it is before.

That feeling of uncertainty isn’t entirely new to entrepreneurs. As business owners, we’re used to taking risks and facing uncertainties head-on. But when you’re not expecting it, it can catch you off guard. In this article, I’ve outlined some of the unexpected challenges that I personally faced in the months and years following the sale of my business. Your own challenges might be different but what’s important is being prepared for the tremendous changes that are in store: and knowing that you can get through it, it just takes time and patience, two things that are often in short supply for us!

Challenges I Faced After Selling My Company

I was holding the pen in my hand, about to put my signature on the last piece of paper that was going to “seal the deal” and hand over the keys to my business; the one I worked so hard to build over the years.

It was the final step after months of challenges, negotiations, and ensuring that I was leaving the company and the people that worked for me in the best possible hands. While I felt exhilaration and pride, I couldn’t help but feel a sense of loss too.

This business was my life, day-in and day-out, over the last 11 years. I grew it from a small, local cabinet store into a thriving $30 million venture. There was endless hard work — with a great deal of time and financial investments made along the way.

After I had sold it, I suddenly found myself with a lot of free time and I didn’t really know what to do with all of it. I had spent so many years living, breathing, and being my business that I was now left with this void. Eventually, different thoughts and challenges started revealing themselves, and I finally had to deal with them.

I’ve done a lot of soul searching over the past two or so years, and have done a lot of personal development as well as I’ve tried to break all of the negative programming that’s built up over the years. Here’s a look at some of the things that I’ve had to learn the hard way, after selling my business.

(Source: Unsplash)

  1. Beware of Compartmentalization

In psychology, compartmentalization is a coping mechanism that allows people to separate thoughts, emotions, or experiences. Basically. your brain is putting different elements into neat, separate sections.

This is very helpful in business. You can go from a marketing brainstorming session to a financial meeting at the drop of a hat. This technique allows you to end one task and dive straight into another, your brain is shifting gears along the way, neatly putting away one topic to focus on the next.

When it comes to our personal lives though, compartmentalization is not so great. When we’re steamrolling ahead with things, burying issues can create a block. It’s painful to uproot these things but at some point, you’ll need to start addressing these issues, working through them as things start to come to the surface. It takes time, honesty, and a great deal of hard work but delaying them only means that you’ll only end up turning to other coping mechanisms instead. In order to be free from your demons, you need to face them head-on, don’t bury them any longer. Stop compartmentalizing everything, you’ll only regret it later on.

2. Stop Suppressing Things

As with the previous challenge, being able to detach emotions from stressful situations was very good for business but not the rest of my life. You can see how the ability to stay calm in stressful situations is good in the immediate short term. Over time though, it can have some pretty detrimental effects. It’s easy to keep moving forward, ignoring any conflicts, fears, or uncertainties that crop up, but for how long? And to what extent? It’s important to make sure you take the time to address issues when they show their ugly head, rather than pushing forward suppressing those uncomfortable feelings, and delaying those unpleasant conversations. I guess if I had to give one piece of advice for this category it would be “learn to face the music.” It’s important to catch these issues before they catch you.

3. Rediscover Your Motivational Drive

Once I sold my business, the world was open to me. But I’d lost my motivation and drive. You spend so much time and energy trying to keep things going with your company that when it’s suddenly no longer there, you’re left with a huge gaping hole in your life, and absolutely no motivation to do anything else. Or at least, that’s how it was for me. That’s a dangerous combination and a very strange place to be in.

(Source: Unsplash)

For me, I had to discover for myself how to stay focused and keep achieving things once again with that same drive. You’ll have to find what makes you tick and what brings you happiness. Then get out there and start making things happen again.

4. Find Your Identity Outside of Business

After 13 years of working, living, and breathing my business, I was my business.

It became my identity and the face of who I was. I was no longer just Gary, but Gary, founder of said company. And once that business that had been my identity for so long was sold, I had to rediscover who I was without the business. I had to get comfortable with being Gary and rediscovering what I liked to do. What inspired me. It took some getting used to. You’d be surprised at how intertwined your business becomes with your personal life, and don’t realize how interconnected it is until you try to break away. Give yourself time. Remember, your business was just one facet of you. Who you really are is not your company, but the person who founded that company in the first place. That person with a big dream and the drive to make it happen. You can start another business if you’d like, or go on to do something completely different. It’s up to you.

5. Don’t Use Work to Escape

No weekend plans? Work instead. Nothing good on TV? Catch up with work. Break up with your girlfriend? Double down with even more with work. For anything difficult that I was facing, I used it as an excuse to work, something that’s true for a lot of people.

During the last two years, a big part of my growth was to break this cycle of throwing myself into work as a distraction, and I needed to learn how to “be.” And this was difficult, partly because I was so used to distancing myself from the real issues that were at hand.

However, once I could confront and understand the “why” behind escaping to work, I learned to be more at peace with myself and just enjoy a quiet weekend with no plans.

6. Escape the Grind

I grew up in a blue-collar family, and it was instilled in me from a young age from both family and my community that the harder you work, the more money you make, and the happier you’ll be.

There’s a grind culture out there that says you have to keep hustling and need to be switched on 24/7. But while that might work for some of us, at least for a while, it’s not the best approach for everyone. Not long-term anyway. Hustling endlessly and earning more money doesn’t necessarily bring happiness. Breaking the cycle and taking the time to find what brings you true joy may bring more fulfillment than being a slave to the grind. Make sure you’re putting your time into things that you enjoy, ones that are fulfilling and connected to your big-picture goals. Remember: being busy does not necessarily mean you are producing great results.

(Source: Unsplash)

You are not Burger King. You don’t need to be open 24/7.

7. Eliminate Your Scarcity Mindset

When I signed over my business, I was soaring. I had just received more money for my business than I could ever have imagined, and I felt like I had won the lottery.

Yet, this feeling quickly shifted. I started to worry and obsess over the money, thinking that now that I had it, I couldn’t lose it. I needed to protect it.

This scarcity mindset isn’t new to the corporate world, with many conditioned to think this way, so this wasn’t surprising. Yet, this mindset actually prevents us from achieving our goals. When we’re in this mode, there’s less collaboration, more fear, and bad decisions are more likely to be made.

So I started to shift the way I was thinking, and when it comes to my new projects, I’m trying to train myself to start operating from a place of abundance. So instead of desperately guarding resources trying so hard to keep what you have, abundance means that you recognize and are grateful for what you have, but you also accept that even if you lose it, you’ll still be okay. Your things, your possessions, don’t define you. It sounds overly simplistic, but it also means being grateful for what you have and training your mind to recognize opportunities and possibilities. Instead of thinking of all the things that could go wrong, think about all that could go right. Stick with it. It takes time to adjust your thinking but it works. You’ll soon be on your way to an abundance mindset, and will start to see new opportunities taking shape as a result.

8. Don’t Fear Failure

Sometimes it doesn’t matter how hard you work; there are obstacles in your path preventing you from success. But — and this is a big one — this does not mean you are a failure. This is sometimes hard to grasp because our view of failure is one of the worst aspects of the entrepreneurial community. And what I learned from my biggest failure is that I probably would not be where I am if it were not for the mistakes made along the way.

Selling my business was a complete rollercoaster ride. But, would I do it again? Absolutely. It’s opened up more opportunities than I’d have ever imagined.

It’s also forced me to think differently and led to some pretty interesting insights along the way. We’re all different, but I hope that by reading some of the mental gymnastics that I went through after the sale of my business that you’ll have an idea about some of the things that you can expect to come up for you as well when selling your business or making another big life change.

Selling something that you’ve worked so hard to build can be exciting, but it can also pave the way for unexpected emotions as well, including a great sense of loss as you close the chapter to something that’s been a very real part of your life for so many years. It’s something that’s difficult to articulate unless you’ve gone through it yourself. Still, know that there is light at the end of the tunnel, and all of that newfound time and freedom that you have can be put to great use. There are countless new opportunities out there just waiting to be discovered. The fact that you’re feeling emptiness means that you were meant for greater things. So pull yourself up by your bootstraps and when the time is right, get back to work. You’ll find the next chapter of your story will start just as soon as you’re ready to be honest with yourself about who you are, and what you want to do with your life.

Are you thinking of selling your business -or facing another big life change? What issues have you run into? I’d love to hear your thoughts, please share them with me in the comments below.

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Gary Nealon

High level coach/consultant for e-commerce companies looking to scale to 8–9 figures. Also Co-founder of Pawzitivity Pets, a group of pet brands and pet blogs.