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The 3 Most Difficult Challenges in Selling Your Business

By Steve Juetten April 28, 2024 Managing Money

Small business owners often ask what the hardest parts are in selling a business. They ask me if the biggest challenges are finding a new buyer, negotiating sales price, informing clients or customer, or something else.

While these tasks are not easy, in my experience the most difficult challenges are:

  1. Letting go,
  2. Running a business while selling it,
  3. Riding the emotional roller coaster.

Let’s dive into these to understand them more, and then I have a suggestion to help you manage these trials.

Challenge #1 Is Letting Go

After you’ve spent years starting your business, nurturing it, suffering through tough times, and growing it, letting go is difficult. If you’re like me when I owned my financial advisor business, I identified myself as a business owner. When people asked me what I did, I confidently said I was a financial advisor and owned my own firm. I read business articles, interacted with other business owners, listened to business podcasts, and interacted with clients and my team every day.

My business was as much a part of me as anything I did. When I began to think about selling my business, in the back of my mind was the niggling thought, “After I sell the business, who will I be?”

This worry may have already crept into your consciousness, and I assure you it’s normal. Every successful business owner becomes part of their business. It’s a requirement and we who run businesses earn the merit badge that says, “business owner.” But once the business is sold, your identity will take a hit and you’ll need to fill the hole in your identity when you’re no longer a business owner.

Challenge #2 Is Running a Business While Selling It

The second big challenge when selling your business is running it while selling it. Once you cross the threshold and commit to selling your business, you’ll take on a second job and one that conflicts with your primary role.

I remember meeting with prospective clients after I decided to sell my practice and feeling a bit like a hypocrite and disloyal. Here I was assuring a prospective client I would help them resolve their financial issues for the long term, and I knew that was not going to be the case. At best I would play a supporting role in their continued financial future and at worst I would not see them after the sale’s date.

Planning with my team also became tedious and draining. We would make long-term plans for marketing, operations and administration, and I knew it would all change before we put the plans into action. Further, I couldn’t tell the team anything up until the last minute. (I’ll write more on this topic in the future.)

An owner can only survive in this muddy and conflicted state of mind for a brief time. There were many times I was tempted to say something to a client, prospective client, or team member, but knew I couldn’t. Until you sign the final agreement, it’s not in anyone’s best interest to say anything because any deal can fall through at the least minute. Once you decide to sell your business, be prepared to struggle with the dual roles.

Challenge #3 Is the Emotional Roller Coaster

The third challenge in selling my business was very unexpected. The emotional ups and downs in the last year of running my practice came at me like a repeating wave. One day I was elated to think about moving on, and the next day I wanted to call the whole thing off. I was equal parts scared, happy, discouraged, patient, impatient, thrilled, angry, disappointed, and just about any emotion.

By the end of the business sale process, I was tired and weary of the emotional toll the pending sale of the business was taking on me. Rationally, I knew it would be okay, but emotionally, I was worn out from the roller coaster of emotions of running a business while trying to sell it.

The Solution

Have a plan, start early, and build your support team.

Create a Plan

Selling your business is a huge deal and takes careful planning to do it well. This is especially true if you’ve never sold a business before. For many business owners, selling a business is sailing in unfamiliar waters. A success plan, like I described in an earlier article on Sixty and Me, is your guide to navigating these waters. A basic plan that touches on the reasons for selling, the ideal buyer, your desired timing and outcomes is like a sailing chart. It will guide you through the shoals and help you to stay on track through the journey.

Start Early

The second most asked question I receive about selling a business (after “What’s my business worth?”) is “How long will it take to sell my business?” The answer is “longer than you think” and “it depends.” As a result, the smart businessperson will start the process of selling her business as soon as possible.

Starting early gives you the time to have a proper valuation done to determine the value of your business, fix broken parts of your business, get your financial records in order, be selective about potential buyers, and effectively communicate with your team. These actions will help the sale process to move more smoothly and help you to maximize the value of your business.

Create a Support Team

Finally, I’m a big believer in creating a support team to help you through the sale of your business journey. The old saying “none of us is as smart as all of us” is undeniably true when it comes to selling your business.

You’ll need a good CPA, business valuation expert, business attorney at a minimum to collaborate with you. Ideally, you’d also have a coach who is familiar with the process of selling a business to assist you. And, finally, you’ll need an emotional support team to guide you and nurture you through the process. This could be close friends, family members or anyone else whom you can trust to keep the sale confidential and not tell you what to do.

Selling a business is a long journey on which you’ll encounter many challenges. However, if you have a plan, start early, and have good support, you’ll meet and overcome any of the trials you meet along the way.

Let’s Have a Conversation:

What other challenges do you anticipate as you think about selling your business? If you have already sold a business, what was the most difficult part of the process for you? Please share your thoughts and comments below. I’d love to hear from you.

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Joyce Ramsay

I started the ‘letting go’ process when my husband walked out 3 years ago and have begun in earnest plans for my retirement. Bought a block of land, designed a shed, designed a house, bought craft supplies and tools, books and materials for projects. I have placed TV advertisements myself but having had no response, I will now place the business with a broker who will have had part of the work done for him as many people have seen the ads. You are right – the emotional toll causes physical and mental stress. I have done all the hard yards of building the business and have a magnificent set of records, inventory and photographs, so I have made the job so much easier for a broker. Wish me well in the sale!

Steve Juetten, CFP®

Congratulations on preparing for your exit. I also love your planning for your future by preparing for what comes next for you. Well done. Using a broker can be effective, but be aware of long lock-up periods with a broker. I’ve heard of brokers requiring a year or more exclusive rights to sell a business. You might give the broker 90 days to see what she/he can do. Best wishes going forward.

The Author

Steve Juetten is the exit wizard for small to medium size business owners. He’s the secret sauce to supercharge effective and profitable business exits through careful planning and nimble execution. Steve is a go-to collaborator to his fellow entrepreneurs looking to win on the way out. Download his free report “Business Exit Made Simple.”

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