One of the most common questions I hear from owners is, “When should I  sell my business?” The answer isn’t the same for everyone — but there are a  few clear signs it might be time to start planning your exit. 

1. Before You’re Worn Out and Tired 

Running a business is demanding. If you find yourself drained, losing  enthusiasm, or feeling ready for a different chapter, it may be time to  seriously consider a sale. The smartest owners set a planned exit timeline — often 3 to 5 years out — to maximize value while they still have the energy  and focus to sustain strong performance. A business with stable or growing  revenues is far more appealing to buyers than one in decline. 

2. While You’re Healthy Enough to Enjoy What’s Next 

Your business has likely demanded years of long hours, tough decisions, and  personal sacrifice. Don’t wait until health concerns force your hand. Many  owners tell me they wish they’d sold earlier, when they could fully enjoy  travel, hobbies, family time, and the freedom they worked so hard to create.  The goal is to sell on your own terms — while you still have time, energy,  and good health to embrace the next stage of life. 

3. When the Business Is Healthy, Even If You’re Not Eager to  Grow It 

You don’t have to chase every growth opportunity — and there’s nothing  wrong with being content. But if you no longer have the drive to expand or  innovate, buyers will see those opportunities and bring fresh energy to  capitalize on them. A healthy business with untapped potential is one of the  most attractive scenarios for buyers. 

Final Thought 

At the end of the day, small businesses and their owners are inseparable.  Your personal goals, energy, and circumstances directly shape the  company’s future. Take the time to have honest conversations with your 

trusted advisors — and if you’d like, I’m always available for a no-obligation  discussion about your situation, business value, and exit options.