888-983-1617 [email protected]

Business.com: When Selling Your Business Causes an Identity Crisis

I recently contributed an article to Business.com offering guidance for entrepreneurs whose personal identity may be tied to their role as business owners. 

Read the article in PDF.

When you run a business, you’re tied to it both financially and personally.

The financial side is obvious: Your company’s success or failure ultimately rides on your shoulders, affecting not just your personal livelihood but that of your employees.

The emotional aspect of being a CEO is something that’s not discussed very much. When you devote yourself to your company’s success over a period of years, working long hours and thinking about it even in your downtime, it affects how you view yourself.

When your personal identity becomes tied to your role as a business owner, what happens if you receive an offer to sell? Can you envision a future for yourself that doesn’t involve your business?

In my work guiding businesses through mergers and acquisitions, my clients include various types of owners who are defined by their jobs to some degree. For each of them, a bit of soul-searching is required to decide whether selling their company is the right choice.

If you’re a business owner, perhaps you’ll recognize something familiar in one of these examples.


Some business owners are beneficiaries – they didn’t start their company but came and worked in it. They’re aware that they started on third base, so to speak. They often feel fortunate to be part of a successful business but wonder if they could replicate that success in a different industry.

We worked with a business owner who was in his late 40s and not confident in his ability to start a new company. He had talked with friends who had sold their businesses and then started ones in different industries, only to realize it was much harder than expected. Many business owners forget that one reason they’re successful is that they’re part of a community and established in one particular industry.

If this situation applies to you, you may be mostly concerned with clearing enough from the sale of your business that you don’t have to work again. Rather than having enough money to start a new business, you might want to avoid the pressure of starting something new that may not be successful.


Every business exists to serve its clients, but some business owners take that duty very personally. One client of ours specializes in solving engineering problems for other businesses. His goal is to create and produce whatever device is needed in a cost-effective way; therefore, each project his company works on is new and unique.

Because this company functions as a “fixer,” it’s understandable that its owner would enjoy being seen as a servant of sorts. If he were to sell his business, he’d have a lot of cash, but he’d also be taking himself out of the problem-solving business. For whom would he solve problems for then? His spouse? And would she even want that?

When you take yourself out of the business you’re in, you either have to give up that part of your identity or find a new area where you can continue to use those skills.


There’s a saying in our field that the closest thing to being king is being the owner of a business. You make decisions, nobody really second-guesses you, and you can either be benevolent to employees or rule with an iron fist. And let’s face it, some people enjoy that substantial feeling of power.

In actuality, the position of CEO is more like being a mayor, since people working for you can always get another job. Part of your day-to-day work is building an environment where your employees want to work.

If you sell the business that you’re in charge of, can you shift your identity and no longer be at the center of things? Appointing yourself mayor at home may not be pleasant for your loved ones.


Business owners contemplating a sale should ask themselves if doing so will really accomplish their goals, or are there other things they could do with their business that would offer the appropriate balance of structure and freedom?

If you’ve staffed your organization in such a way where it can operate without you, then you might have the option of transitioning to a less-active role, such as chairman of the board. If you don’t have that organizational structure – which in itself might say something about your personality – then you might have fewer options when you’re ready to exit.

This type of major decision won’t necessarily come at the end of your career. Sometimes it happens midway through, and for some business owners, it happens more than once during a career.

While the right choice will be different for every person and every situation, the first step in all cases is taking a realistic look at the needs of your stakeholders – yourself included – and understanding the available options. The best investment bankers and M&A advisers are counselors who can help you understand and compare alternatives.

3 Signs an M&A Deal Is in Trouble

Read the article in CFO.Spotting signs of trouble early is critical for CFOs to prevent a deal from derailing. Not every CFO will experience M&A firsthand during their career. But those who do typically find that their existing skillset makes them a crucial asset...

4 Tips for Pitching Investors in Today’s Economy

Read the article in CFO.Any company that intends to grow past a certain point eventually reaches the familiar milestone of pitching to private capital sources in hopes of securing additional funding. Those businesses that tend to be most successful are the ones that...

Resolving Conflicts in a Family Business

Read the article in Small Business Current.When family members run a business together, the experience often draws them closer, but there are inherent risks as well. Having years of personal history with one’s co-workers can sometimes lead to non-work disputes...

Oaklyn Consulting Congratulates Proof of the Pudding on Acquisition by Bruin Capital

Oaklyn Consulting congratulates Atlanta-based catering, food service and event company Proof of the Pudding on its recent acquisition by Bruin Capital. Oaklyn Consulting assisted Proof of the Pudding in evaluating potential partners and negotiating the transaction....

Analyzing Broad vs. Narrow M&A Deal Processes

We respect the unique M&A market insights that Sutton Place Strategies, an affiliate of Bain & Company, creates from its business development work with PE firms. SPS Founder and CEO Nadim Malik gave a presentation at ACG Boston's M&A Outlook forum in...

How To Work Through Conflicts In a Family Business

Creating a family business comes with a lot of positives, as well as a lot of challenges. Here’s how to handle those conflicts as they arise. Thanks to The American Genius for having me! Read the article in PDF.Anyone who’s managed a business with other family members...

Takeaways from Axial’s Recent ‘Dead Deals’ Analysis

Those of us who negotiate M&A transactions for, and with, small- to mid-sized businesses know a few hallmarks of the process: For any company, there is a limited universe of buyers. Each buyer's interest is unique, so average valuations are not reliable indicators...

Who We Helped in 2022

At the start of every year, we at Oaklyn Consulting like to look back at the past 12 months to reflect on projects accomplished and lessons learned from our clients. Building on our achievements from 2021, Oaklyn Consulting worked with 34 organizations in 2022 on...

Monty Bruell Interview with Business Radio X

Our Monty Bruell sat down with Business Radio X to discuss succession planning in minority and women-owned businesses. Listen on Spotify or Amazon Music or read the transcript below!INTRO: Broadcasting live from the business RadioX Studios in Atlanta, Georgia, it's...

Succession Planning for Minority and Female Business Owners

For the founders of minority and women-owned business enterprises (MWBEs), succession planning takes on a deeper significance. Our Monty Bruell explains in a guest column for Memphis Business Journal. Read the article in PDF.Any entrepreneur approaching retirement has...