Deciding to Exit

The decision to sell your company is a critical one. You’ve invested years or decades painstakingly building your business, and you’ve made countless sacrifices along the way. It’s an emotional decision that shouldn’t be taken lightly. In the words of the American science fiction writer Philip K. Dick, don’t try to solve serious matters in the middle of the night. 

When contemplating such an important decision, there are four critical factors to take into account:

  1. Your goals, including personal, financial, and business 
  2. Internal factors, such as emotions 
  3. External factors, including timing and competition 
  4. Your business’s value and exit options 

You can’t decide to sell your business by following a simple checklist. Instead, the determination should be made deliberately, taking all factors into consideration and balancing emotion and intuition with facts and logic. 

While the framework I outline below is useful, these four factors aren’t all-encompassing, but are meant to be jumping-off points to further explore this important decision. Every entrepreneur’s situation is different, and you may need to consider additional factors I don’t address here. Regardless, start by considering these four factors and see where your journey takes you.

Factor 1: Your Goals

“You are that which you are seeking.”

– Saint Francis of Assisi, Italian Friar

Start the process by writing down your goals – understanding what you want is the first step toward achieving your objectives. Only after you clarify your long-term goals can you examine how selling your business will move you closer to them. 

You must take many factors into consideration when deciding to sell your business, and considering all elements simultaneously can be overwhelming. Starting with your goals simplifies the decision-making process. The risk in selling your business before examining your goals, is that you may make a decision that doesn’t align with your goals. As a result, you may find yourself backing out of the sale or living with regret after you no longer own your business.

Questions to Help You Target Your Long-Term Goals 

To gain a better focus on your goals, ask yourself these questions:

  • What are my long-term goals? 
  • Would selling my business help me achieve my long-term goals? 
  • What am I trying to accomplish now? 
  • Which of my goals are the most important?
  • How does the sale of my business help me achieve my goals?

Align your long-term objectives with the sale of your company. If your business is preventing you from achieving your long-term goals, consider selling your business. If selling your business is critical to achieving your goals, spend additional time planning your exit to ensure the sale accomplishes your objectives.

Is your goal to sell your company and become financially independent? If so, have your business valued and develop a strategy for increasing the value of your business, then track your results to ensure you meet these objectives. You should also prepare a personal financial and tax plan to make certain your exit will help you achieve your financial goals and mitigate the tax implications of the sale. When it comes to taxes, remember Albert Einstein’s keen observation: “The hardest thing to understand in the world is the income tax.” Unless you’re smarter than Einstein, consider hiring a tax expert to advise you.

Is your goal to sell your business so you can start another business or pursue an opportunity in another industry? If so, consider your lost opportunity cost and the cost of remaining in your business. 

What are you losing now by not pursuing your next business or opportunity, or a different goal or dream? Ideas are infinite, but time is finite. You have a limited number of ideas you can pursue in your lifetime, so consider what other opportunities owning your business is preventing you from pursuing. 

Again, the decision to sell your business should always begin with a thorough and careful review of your long-term goals. If your goals are unclear, then the decision to sell your business will be based on a weak foundation. As a result, it will be harder for you to commit to the sale without a definite objective, and this uncertainty will minimize your net proceeds from the sale.

Clarify Your Financial and Non-Financial Objectives 

If you must sell your business to achieve your financial goals, consult with a financial planner to ensure you can meet your financial objectives upon a sale, and meet with a CPA to consider the tax implications of the sale.

For most owners, the sale of their business is critical to achieving a personal long-term objective. Many entrepreneurs depend on the sale to help them accomplish their financial target. But it’s important to separate your financial goals from your non-financial goals to establish crystal clear objectives. 

It’s not always necessary to start your planning process with numbers – after all, money is always a means to an end and not an end to itself. Remember as business author David Baughier once said, Once you have enough money, it’s not about the money.Instead, ask yourself what’s behind the money. First, clarify your long-term goals, and then assign numbers to the goals, if possible. 

Ask yourself these key questions to clarify your financial and non-financial goals:

  • What are my financial goals? How do these fit into my long-term plans? 
  • What’s more important – my financial goals or other goals I have set? 
  • What am I going to do with the money? 
  • Is my goal to take money off the table and diversify my risk? If not, what am I going to do with the money?

Other Passions You Can Pursue if You Sell Your Business 

“The price of anything is the amount of life you exchange for it.”

– Henry David Thoreau, American Author and Philosopher

When deciding to sell your business, consider the lost opportunity cost. Pursuing opportunities is a mutually exclusive decision if you believe in focus. If you chase two rabbits, they’ll both escape. Chasing more than one objective at a time dilutes your focus and lowers your chance of success. There’s a significant lost opportunity cost to holding onto a business where you’ve lost your passion. What other opportunities are you passionate about that you could be pursuing if you didn’t own your business?

While the decision to sell your business can’t always be reduced to numbers, it can be helpful to look at a sale from multiple angles, including both quantitative and qualitative perspectives.

In addition to lost opportunity costs, you need to consider the current state of your industry. Not all industries are created equal and careful consideration must be given as to when to jump from one ship to another. 

Many entrepreneurs make the mistake of thinking that the grass is always greener on the other side and that other industries offer more potential than the one they’re currently in. If you believe your industry is in decline, consider consulting with other seasoned entrepreneurs, industry experts, or an M&A advisor or investment banker to get their take. Others are likely to have experience in various industries and perspectives that you lack.

If your other goals are primarily non-financial in nature, your decision can be especially difficult, and you must carefully weigh your options. 

What is owning your business precluding you from doing? What is that experience worth to you? 

Only you can decide. Life is short, but you should take your time when making this important decision.

Factor 2: Internal Factors

“If opportunity doesn’t knock, build a door.”

– Milton Berle, American Actor

Here are more questions you should consider:

  • Am I happy? Am I really happy? 
  • Is my business making me unhappy? 
  • Would selling my business make me happier? 

Entrepreneurship is a struggle. No entrepreneur is happy 100% of the time. But perhaps the French poet, Charles Baudelaire, was right when he said “Everything considered, work is less boring than amusing oneself.” Whether or not you agree with Baudelaire, look at yourself and your business objectively and determine if a change might make you happier. At the same time, though, beware of trading one set of problems for another. 

Why Making a Commitment to Sell Your Business is a Big Deal

Are you truly committed to the process of selling your business, or have you made this decision on a whim?

Move forward with your plans only if you’re fully committed. But be aware that doubts will remain no matter how committed you are. Be deliberate in making your decision, so you can deal with doubts as they arise. Talk with trusted friends who have successfully sold their businesses. Journal. Read. Explore your decision from all angles. 

Selling a business is a process, not an event. The process of preparing a business for sale and successfully exiting takes several years for most entrepreneurs. Shortcutting the procedure can leave money on the table and waste a significant amount of time if you begin the sale only to change your mind later. Only you can answer if you thoughtfully and purposefully made this decision or if an impulse is driving you. If you’re still on the fence, take more time to explore the decision fully before making a final determination.

Take Your Happiness Into Consideration

Would selling your business make you happier? If you’re facing challenges in your company, ask yourself if the root of your problems is a lack of management skills or if your obstacles are caused by external factors beyond your control, such as increased competition in your industry. If your issues are the result of inadequate management skills, trading one business for another is unlikely to solve your problems. 

On the other hand, some industries aren’t known for creating happy entrepreneurs. These include businesses that may have less-than-ideal customers. When was the last time you saw a happy divorce lawyer? If the general environment of your industry is unhappy and you value your well-being, consider making a change.

Would you keep your business if it made you happier? Would you keep your business if you could revamp your schedule and spend 80% of your time on high-value activities you enjoy and less time on all the other minutiae?

If so, restructure your business to focus on what you love to do and take advantage of your strengths. If you’ve lost passion for your industry and have a strong gut feeling you need to make a change, it’s time to develop a definite plan to exit your business.

Address Your Burnout and Boredom Before Deciding to Sell

Look in the mirror and ask yourself these questions:

  • Am I burnt out? 
  • Have I taken a vacation recently? 
  • What other options have I considered or attempted to cure my burnout?

Burnout is normal in all endeavors, and all entrepreneurs should make time for regular relaxation to de-compress. Professional athletes periodize their training. CEOs take regular time off to recharge. You should do the same to both prevent and treat burnout.

Fatigue is normal if you aren’t taking time off. Just because you’re burned out doesn’t necessarily mean you should sell your business. First, determine the cause of your burnout and then evaluate if selling your business will be a cure, or if other measures are more appropriate for rekindling your passion.

If your burnout is due to problems with your employees, it’s time to either upgrade your management skills or upgrade the team itself. Trading your business for one in another industry won’t help if people-management issues are at the root of your burnout.

If you haven’t taken a vacation in a long time, other methods are available for relieving burnout. Ideas could include stress-management techniques or restructuring your business to minimize activities you aren’t good at or that cause you stress. First, set out to relieve your burnout. If you find you still lack passion for your industry, are bored, and in need of a change, and if you’ve attempted to address your burnout and boredom one too many times without effect, then perhaps it’s time for a change.

Deciding How to Fill the Void After Exiting Your Business 

The question to ask yourself isn’t, “What will I do with my money when I sell my business?” The real question is, “What will I do with my time when I sell my business?”

To be sure, the matter of what to do with the rest of your life is a difficult topic to face. Most business owners are so busy that they don’t have time to confront the deeper issues in their lives. They’re so occupied playing whack-a-mole in their business that they don’t have the bandwidth to face life’s existential questions. 

After selling your business, it might be the first time in decades you’ve had the freedom to decide how you spend your time. Will you fritter away your days buying toys, or do you plan to pursue something more meaningful? How you spend your time should be based on your values. Your values are the foundation on which you make decisions. Having a clear and documented set of values makes the process of deciding how to allocate your time easier. 

After all, as author Michael LeBoeuf once said, “Waste your money and you’re only out of money, but waste your time and you’ve lost part of your life.”

Selling your business will leave you with time. If you don’t have another passion, you’ll be left with a void, leaving your business to fill that empty time. If this void isn’t filled, your being may lack meaning. Sitting around the pool sipping margaritas on a giant, inflatable pink flamingo can become unfulfilling after a while, especially for driven entrepreneurs. Of course, some may never tire of this. Examine your values and goals so you don’t create a void after the sale. Don’t avoid the real question by drowning yourself in material pleasures.

Factor 3: External Factors

“We’ve done better by avoiding dragons than by slaying them.”

– Warren Buffett, American Investor

Once you’ve considered your internal factors, it’s time to take a broader look at the external factors that will affect your decision. Industry conditions and competition will play a large part in how smooth, and ultimately successful, the sale process is for you.

Choosing the Right Time to Sell Your Business

When it comes to selling your business, the cliched expression applies – timing is everything. While timing the sale of your business is difficult, it can be done. The ideal time to sell is when your business and industry are about to peak. Consult with industry veterans to obtain their opinion regarding the current market cycle of your industry. Consider both narrow industry cycles and broader macroeconomic cycles. But remember that, as with most important decisions, the timing will never be perfect. 

Align the timing of your goals with the timing of the sale of your business, industry trends, and market activity, if possible. Otherwise, avoid selling in a severe economic or industry downturn. Your revenue should be stable and preferably growing by the rate of inflation or more when you put your business on the market. If it’s not, have an expert analyze your business to determine if it makes sense to stabilize your company’s revenue before putting it up for sale. 

Consider Competition, Capital, and Cash Flow 

You can bet that Warren Buffett, the Oracle of Omaha, has asked himself these questions more than once regarding specific investments:

  • Is competition becoming stronger in my industry? 
  • Are new venture-backed entrants threatening my market share? 
  • Do I have enough capital to fight a competitive industry war? 
  • Are indirect competitors threatening to permanently change the structure of my industry (e.g., Uber vs. the taxi industry, Airbnb vs. the hotel industry, online news vs. traditional news)? 

If competition is increasing and becoming more fierce by the day, but you lack the passion and capital to compete, exit as quickly as possible if you can. The value of your business will decline proportionally to a decline in your revenue and cash flow. Face the inevitable conclusion and sell while you have something to sell. Unfortunately, I see too many entrepreneurs hang on for too long, only to have nothing valuable left to sell. 

Don’t make this common mistake. 

Factor 4: Value and Options

“Don’t be afraid to give up the good to go for the great.”

– John D. Rockefeller, American Business Magnate

Knowing what questions to ask yourself is half the battle. Consider the following when it comes to the value of your business:

  • Have I had my business appraised recently? 
  • Am I aware of current multiples in my industry? Have multiples remained steady within my industry, or have there been significant variations over time? 
  • Do I know what changes I need to make to unleash the value of my business? Do I know what my business would be worth if I made these changes?

Consider these questions, and many more, as you begin to explore your exit options.

Know What Your Business Is Worth 

Your business is likely one of your most valuable assets and may comprise the majority of your net worth. Intelligent financial planning is difficult without having an accurate idea of the value of your most valuable asset – your business. 

It makes sense to pay a professional to value your business and have an idea of the steps you can take to increase its value. It’s best if you and your business are prepared at all times for the unexpected buyer, and that you regularly take steps to increase the value. The buyers most likely to pay the highest price are those who approach you directly, unsolicited. So be ready for them.

Consider diversifying your risk if your net worth is highly concentrated in your business. There are many options for diversifying your risks, such as a recapitalization or an outright sale. An appraisal of your business is the most prudent place to start and can help you make an intelligent decision.

Knowing what your business is worth also enables you to determine a bottom-line price if a competitor approaches you out of the blue. Without such planning, you may be caught off guard and end up selling your business for far less than what it’s worth.

Understand Your Exit Options 

Ask yourself these questions that go to the heart of the choices you’ll face:

  • What are my options for exiting my business? 
  • Should I consider selling or gifting my business to family members? 
  • Is my management team, or someone on the inside, a potential fit? 
  • Is a sale to a competitor most practical? 
  • Is a private equity firm likely to buy my business?

Most entrepreneurs lack the experience to determine exit options most suitable for their business that will unlock the most value. That’s why you should consider having a third party perform an unbiased assessment of your business.

This assessment should lay out your exit options and steps you should take to prepare your business for sale. The risks and opportunities vary depending on who you sell your business to. Different steps will need to be taken depending on whether you plan to sell your business to a strategic buyer, a competitor, or a financial buyer. You should carefully consider these issues before deciding which exit option to pursue.

There are also creative alternatives to a conventional sale. Again, before proceeding, establish your goals. With clearly defined goals, a professional can easily and efficiently lay out the most practical exit options for your business based on your goals, along with tips for reducing the risk associated with each option. In the words of Warren Buffett – Should you find yourself in a chronically leaking boat, energy devoted to changing vessels is likely to be more productive than energy devoted to patching leaks.” 

Determine the Direction the Value of Your Business Is Going 

Sell while you’re able to extract any remaining value. If the value of your business is decreasing and you lack the drive to turn it around, consider the lost opportunity cost of holding onto your business. If revenue continues to decline, so will the value of your business. Selling a business with consistently declining revenue is difficult, but it can be done. Selling a business with stable or increasing revenue is far easier.

Take an honest look and ask if you can turn your business around. If you’re burned out and competition is increasing, it’s time to get out. If the decrease in the value of your business is due to a one-time event or an internal factor and you have time to cure the problem, then do so.

How to Know When Your Business Is Ready to Sell 

These aren’t always easy questions to answer, which is all the more reason to ask yourself:

  • How salable is my business right now? 
  • Are there deal-killers present in my business that need to be fixed? If so, how long will it take to fix them? 
  • Is it worth the time and energy to attempt to straighten out these issues, or is it best to sell my business in its current state? 
  • What is my personal ROI if I fix these issues before selling my business? 
  • What is my lost opportunity cost in attempting to cure these potential deal-killers? 
  • Could my time be better used elsewhere?

Ideally, you should invest several years preparing your business for sale to maximize its value. The more salable your business, the more your business will be worth. There are two ways to improve salability – eliminate deal-killers and optimize your business’s value drivers. 

Start by fixing any deal-killers. These could include inaccurate financial statements or undocumented intellectual property, or one of a hundred other issues that an investment banker can help you identify. Once you address these issues, calculate the ROI on the remaining potential changes and start with the highest ROI tweaks.

Not every business owner has the time and energy to fully prepare their business for sale. If this describes you, continue to make changes while your business is on the market. If your business isn’t fully prepared, you may still be able to sell it but expect to receive less than full value.

Key Points 

“See things in the present, even if they are in the future.”

– Larry Ellison, American Inventor

Choosing whether to sell your business will be one of the most important decisions of your life. Use the framework outlined here for making this determination: 

  1. Goals: Start by considering your objectives and lost opportunity costs. This is the foundation of your decision. 
  2. Internal Factors: Address the emotional or internal factors of a sale – namely, those relating to happiness. This step takes time to do correctly, so don’t rush it.
  3. External Factors: Once you’ve thoroughly explored your emotional objectives, consider the external factors, such as the timing of selling your business and the state of your industry. 
  4. Value and Options: Finally, you can commit to the process after considering your goals and both the internal and external factors. Only then should you explore the additional facts related to the decision – such as timing, value, exit options, and salability.

By following this framework, you can make sound decisions on your company’s future with the assurance that you have taken the most important factors into consideration.

Learn More

The idea of being happy in business is one which doesn’t get talked about much, but I had an entire conversation about exactly this topic in my M&A Talk podcast episode titled Happiness: How it Relates to M&A and Entrepreneurs with Marco Robert. You can join us for this unusual conversation by going to the Resources section of our website at