Navigating the Emotional Journey of Operating and Selling Your Business

Starting a business is one of the most exhilarating and terrifying decisions you’ll ever make. Whether you built your company from the ground up or took over a family business, you know the emotional rollercoaster that this entails. The sleepless nights, the tough decisions, the constant battle between optimism and fear, it’s all part of the journey. And yet, despite the struggles, you push forward because you’re passionate and you believe in what you’ve built.

I know this because I’ve been there. I’ve founded, grown, and successfully exited businesses my entire life, and I’ve worked with countless business owners who have walked the same path. I also know that when it comes time to sell, the emotional stakes are higher than ever. Selling a business isn’t just a financial transaction, it’s deeply personal. It’s the culmination of years, sometimes decades, of hard work, risk-taking, and sacrifices. And for many owners, it’s one of the most challenging transitions they’ll ever face.

To truly understand the weight of this transition, it helps to look back at the pivotal moments that have shaped your journey as a business owner—moments I’ve faced throughout my own journeys as well.

The Beginning: Excitement and Uncertainty

The day you decide to start a business is filled with a mix of excitement and anxiety. Will it be successful? Do I have enough money? Can I hire the right people? You’re second-guessing yourself, but you push forward, fueled by the vision of what your business could become.

The Grind: Facing the Daily Struggles

Once you’re in the trenches, reality sets in. Maybe revenue isn’t where you need it to be, or production and quality control issues arise. Some weeks, you’re just trying to survive. Fear and doubt creep in—am I making the right decisions? Do I have what it takes to lead this company? Even when you experience success, do you truly take the time to celebrate it? And when failures come, do you take the time to learn from them, or do they just add to the weight you carry? Who can I talk to when I can’t be totally open with my employees?

The Shift: Thinking About Life Beyond the Business

As time goes on, your worries start to change. Instead of focusing on keeping the business running, you start thinking about your own future. What happens to my employees when I step away? Will my business survive without me? What is the legacy I want to leave? Do I have enough money for retirement or my next chapter in life? And perhaps most importantly, what’s next for me personally? What impact will it have on my family? These questions can be overwhelming, leading many business owners to put off thinking about an exit strategy altogether and burying their head into their business.

The Dread: The Uncertainty of Selling

The decision to sell is rarely easy. You might feel pressure from loved ones and others close to you. You start seeking advice from family members, friends, or advisors like your accountant or company lawyer, but the more opinions you get, the more confusing it becomes. You’re torn between days when you wake up feeling energized, hopeful, and optimistic about the future and other days when you don’t want to get out of bed to go into the office. You might even start fielding calls from private equity firms or strategic buyers who promise you a lot of money and a quick close—but how do you know if their interests align with yours and if it is a good opportunity or not?

The Unknown: Life After the Sale

Even once the sale is complete, the emotional journey isn’t over. Many business owners find themselves lost after selling. The routine, the relationships, the sense of purpose, it’s suddenly gone. Friendships built over the years in business begin to fade. Without a new plan, post-sale life can lead to feelings of isolation, boredom, and even depression. Healthcare, financial planning, and finding a new sense of purpose become critical concerns. Spouses, although supportive, start asking you what you are going to do next. Suddenly what you are going to have for dinner becomes a major stressful decision!

You Don’t Have to Go Through This Alone

I understand firsthand how emotional, complex and difficult this journey can be. That is why I started my firm, to help business owners navigate this journey successfully, ensuring you’re financially and emotionally prepared for life before, during and after the sale. This is a process that no business owner should have to tackle alone.

Be sure to check back for Part 2, where I’ll share four essential steps to help you navigate the sale process with confidence and clarity. These strategies will not only ensure you have the proper strategic exit plan, a smoother experience and transition, but will also help you achieve the best possible personal and professional outcomes.

In the meantime, please don’t hesitate to reach out if you have any questions or need guidance. Me and my team at RVR Consulting Group would be happy to discuss your situation and how we can assist you through this critical transition period.

The first step is a conversation, which we would be happy to help you schedule. Please call our office at 407.677.0400 or email info@rvrteam.com and we can discuss your situation.