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This blog post is an excerpt from the Trelus Transition Readiness Webinar Series featuring Denise Logan, Business Transition Expert and author of The Seller’s Journey, and Curt Cyliax, Managing Director at Strategic Exit Advisors.  

If you’ve considered selling your business, or are actively in the process of taking it to market, are you prepared for the full range of emotions you may experience?

It’s easy to focus on the logistical and financial aspects of selling and neglect the emotional side. Maybe you assume that you’ll have uncomplicated feelings of happiness as soon as the deal is sealed. Maybe you want out of your current company very badly, and can’t imagine being sad on your last day. Or maybe you know this will be a sensitive time for you, but aren’t sure just how to unpack those feelings.

Denise Logan, former business owner and author of The Seller’s Journey, has encouraging news: it’s possible to ready yourself for strong emotions and accept them with grace during the sales process. 

Nicknamed “The Seller Whisperer,” Logan works one-on-one with business owners to help them think through the emotional aspect of selling their company. “I’m doing for others what I needed someone to do for me at the beginning of my career,” she says. Logan sold her own business in her late 30s and experienced the wide-ranging, unpredictable emotions that can emerge when an owner says goodbye. She wants other business owners to be better prepared than she was.

Why are emotions so complicated for business owners who sell? And what can you do to manage it well?

Why the Emotional Rollercoaster?

Why do so many business owners find the emotional journey challenging? Logan identifies a couple of common reasons.

Thinking “transaction” instead of “transition.”

Many business owners, says Logan, are directed by their advisers and by cultural norms to focus on the logistics and finances of a sale, leaving little room for other reflection. When you don’t prepare for strong emotions, they can be harder to deal with.

“We think about the sale of our business, and often we focus on it as a transaction,” Logan explains. “In reality, it’s the single largest professional transition in our adult life.” 

She points out that most people try to emotionally prepare for other life transitions like going off to college, getting married, or having a child. If we don’t, we may be steamrolled by the adjustment period. Why should stepping away from a business be any different?

Leaving too early or staying too late.

Part of the problem, says Logan, is that “business owners have been led to believe that there will be a magical moment when we know it’s time, and somehow we’ll be able to make an exit smoothly.” In reality, that kind of internal clarity seldom hits owners over the head at just the right time. It takes intentional planning to know when to step away.

Logan believes she waited too long to leave the legal firm that she built in her 30s. By the time of her exit, she was so burnt out that she dreaded her workday. In contrast, she later met a business owner who took his business to market three different times, and realized each time that he wasn’t ready to let go.

Neither Logan nor her friend had correctly anticipated what it would “feel like” when it was time to leave. They were waiting for spontaneous clarity that never arrived. They would have benefitted from better planning and envisioning their desired futures.

How to Prepare for the Emotional Journey of Selling

“The [emotional] journey that an owner goes through to sell their business is the same whether we’re talking about a $50,000 hair salon or a $500 million company,” Logan says. This commonality can help business owners know what to expect.

Logan identifies five strategies you can use to lay the groundwork for an emotionally healthy exit.

  1. Take care of your relationships.

Exiting a business can shine a spotlight on any problems in your relationships. Dynamics may have changed between you and your loved ones over the years, and those changes are easier to see when you aren’t busy at work every day. This can add disappointment, anxiety, and even grief to the exit process.

For example, Logan once worked with an owner who was about to sell his business and buy a boat to sail around the world. At the eleventh hour, he discovered that his wife hated the sailing plan and wanted nothing to do with it. He was crushed, having envisioned the two of them adventuring together. Rather than face this grief and disappointment, he tried to sabotage the impending sale by suddenly asking for more money, hoping that the buyer would walk away and he wouldn’t have to retire.

It’s important to face up to relational conflicts before the moment of your sale is imminent.

  1. Map out a very specific post-exit plan.

Once you exit the business, especially if you are retiring from full-time work, you must have a specific plan for your daily life, Logan says. The stereotypical picture of retirement—moseying around a golf court, lounging poolside, catching up on years’ worth of television—is often boring and uninspiring in real life, leaving former business owners feeling lost and disillusioned.

“Retirement for [our generation] will not be like retirement for our parents and grandparents,” Logan says. “We’re not going to be satisfied just playing golf and waiting for Wheel of Fortune to come on.”

Know how you will fill your time. Will you volunteer with a specific organization? Will you join a group or club? Who will you socialize with, and when? Do you hope to launch a new business, and if so, how soon?

“Know precisely what you will do,” Logan says. “Where will you go? What will the first month look like? What do the first 3 months look like? The first nine months? The first year? The first three years?”

  1. Identify which needs your job is filling for you.

As you plan your post-exit life, take into account the needs that are currently being filled by your business, other than money. How will you meet those needs when the business is gone?

A few common needs that businesses may fulfill for owners include:

  • The thrill of accomplishment 
  • Daily purpose
  • Feeling needed by others
  • Sense of community or inclusion
  • Opportunity to live personal values
  • Professional affirmation and credibility
  • Friendship with coworkers and employees

Your needs don’t change just because you exit a business, so make sure you have a plan to continue meeting them.

  1. Find supportive confidantes to help you unpack your emotions.

You’ll need at least a few trusted people to talk to when emotional issues inevitably arise. These confidantes will need to understand your perspective and listen to you without judgment.

Logan shares another anecdote of a business owner in his late 30s who was going to sell for so much money that he wouldn’t have to work again. He became depressed when he realized that he would be alone all the time, since all of his friends would still have jobs and he would no longer have coworkers. When he tried to share this worry with a close friend, the friend chastised him for focusing on problems when he was about to be rich. This didn’t solve the owner’s problem, it just kept him from seeking support for it.

Find individuals who can listen to all of your feelings and remain supportive. Consider confiding in a spouse, an adviser, a minister, or a mental health professional.

It’s a good idea to prepare your confidantes for the post-sale emotional rollercoaster. When friends and loved ones understand that up-and-down emotions are normal during business sales (even very positive sales), they’ll likely be more patient and less confused if you seem troubled at times.

  1. Anticipate your trade-offs.

Any time you make a major change, even a good one, there will be trade-offs. You might be pleased as punch about the dream house you bought—but now you live farther away from your favorite restaurant. You could be excited about going back to school—but it will place new constraints on your free time.

Trade-offs are not a sign that something is wrong with your decision. They’re just part of life. 

This is true for leaving a business, too. You may lose routines, contacts, and fun experiences that you wish would never end. If you identify those pieces of the transition beforehand, you won’t be caught off guard when you have moments of sadness about them. Reassure yourself that these feelings are normal and not necessarily a sign that you made a mistake.

Time to Go

Whether you love your company, have mixed feelings about it, or can’t wait to leave, you can’t fully predict what you will feel throughout the process. It’s important to be mindful of your internal state as you exit, and to take care of your mental health.

Learning more about what you may feel, and finding supportive allies to see you through, will help create a better experience and set you on the path to a joyful life after the sale is complete.

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