How to Decide Whether to Sell or Keep Running Your Business

When to sell your business? It depends on your goals, challenges, and even your personal feelings about control and legacy. In a lively discussion, James and VirtualDOO.com’s Lloyd Thompson look at the critical factors that influence this monumental decision.

Podcast: Download (Duration: 42:32 — 58.7MB)

Deciding whether to sell or keep running a business is one of the toughest choices entrepreneurs face. It’s not only about the money — it’s about emotional ties, future plans, and the hard work invested over years.

In a recent conversation, James and VirtualDOO’s Lloyd Thompson explore this topic, unpacking everything from financial motivations to the emotional complexities of letting go. Here’s a deep dive into the factors you should consider before making that call…

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Table of contents:

1. Financial motivation: the obvious and the overlooked
2. Emotional attachment: it’s more than just a business
3. Are you still excited? Rediscovering passion or moving on
4. Control, legacy, and succession
5. Market changes and the future
6. Final thought: start with an audit

Financial motivation: the obvious and the overlooked

The financial aspect is often the first reason people think about selling a business. Selling can offer a lump sum payout, perhaps three, five, or even ten years’ worth of profits.

But financial motivations aren’t always straightforward. If you’re heavily involved in daily operations, selling might require an “earn-out” period, meaning you’d need to stick around for a while to help with the transition. Earn-outs can extend to three years, limiting your freedom and control.

If a clean break sounds appealing, make sure you’ve built a team that can operate independently. James gave the example of a business owner who was paid upfront with no ongoing responsibilities, because the business ran smoothly without them. For many, this is the dream scenario.

If you’re considering selling, think about how much you’re willing to stay involved after the sale and if a financial exit aligns with your future lifestyle.

Download Sell or Keep Your Business? 10 Things to Consider (and the PDF transcription)

Emotional attachment: it’s more than just a business

For some, a business is more than a source of income—it’s part of their identity. If you’ve poured years into growing your company, the thought of selling can feel like letting go of a piece of yourself. Many entrepreneurs, James notes, experience a sense of loss after selling, particularly if they’ve tied their identity to the business.

Lloyd compares it to “empty nest syndrome” for business owners who’ve built teams, nurtured company culture, and developed a brand that reflects their values. Selling a business you’re emotionally invested in can be tough, and it’s important to acknowledge that. If selling feels like “divorce” rather than a strategic move, consider your emotional readiness.

Are you still excited? Rediscovering passion or moving on

One powerful motivator to sell is burnout. If you’ve lost excitement for the business, it might be time to let go. But not all frustrations require a sale. Often, dissatisfaction comes from operational burdens that could be eased by hiring the right help. For instance, bringing in an operations expert or fractional manager could allow you to step back, turning you from the daily operator into an investor.

Many entrepreneurs find that when they’re no longer involved in the day-to-day grind, their passion for the business returns. If the main issue is burnout, rather than the business itself, consider a middle path: delegate more and explore your options as an investor, rather than diving straight into selling.

Control, legacy, and succession

Selling also means relinquishing control. For some, that’s freeing. For others, particularly those who see their business as a legacy, control is essential.

James has seen how some business owners consider leaving their company to family or close friends, but this comes with its own risks. Sometimes, handing the reins to someone you know personally isn’t as effective as finding a professional with proven expertise.

The idea of legacy also brings a deeper question: Does leaving something behind really matter? It’s natural to want a business you’ve built to continue thriving, even if you’re no longer there. It certainly appeals to organized psyches like Lloyd’s. James suggests, however, that focusing too much on legacy can sometimes be a trap.

What ultimately matters most is your fulfillment while you’re here, not necessarily what others think of the business once you’re gone.

Market changes and the future

In today’s rapidly changing world, businesses must keep up or risk becoming obsolete. If your industry is on the brink of transformation—think about traditional call centers facing competition from AI—selling may be a wise move.

Note, though, says Lloyd: a conditional payment scheme is not what you’d want under those circumstances.

Alternatively, if you see your industry evolving and you’re excited about being part of that change, it might be worth sticking around. Your choice to sell or keep could depend on whether you’re prepared to pivot with the market or prefer a clean exit.

In many cases, as James points out, the sale process itself changes nothing. Your challenges evolve, but they don’t disappear. If you’re on the fence about selling because you hope a sale will eliminate your problems, consider that selling might just swap one set of issues for another.

Final thought: start with an audit

If you’re still undecided, consider an audit or review of your business. Having an outsider assess your operations can reveal opportunities you might have missed and help you identify areas for improvement. Often, entrepreneurs are so close to their work that they can’t see its true potential. An audit like those Lloyd and other operators offer could show you that there’s more value in keeping the business than you initially thought—or confirm that it’s time to move on.

Ultimately, selling or keeping a business is a personal decision with financial, emotional, and strategic implications. Start by asking yourself if you’re ready to walk away or if you’d prefer to reimagine your role within the company. When you consider your financial needs, emotional readiness, and vision for the future, you’ll make a choice that aligns with your goals and values.

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