Why Waiting Until You’re Ready Is Often Too Late

Why Waiting Until You’re Ready Is Often Too Late

Many small business owners tell themselves they’ll think about success or selling the business “when I’m ready.” It sounds sensible, why plan your exit if you don’t intend to leave anytime soon? In reality, waiting until you feel ready to step away is often too late. Life can throw curveballs, opportunities can appear unexpectedly, and if you haven’t prepared, you and your business may find yourselves scrambling. As part of our January theme, Beyond The Exit: Planning for What Comes Next, this discussion will explore why proactive succession and transition planning is so critical. We’ll see how a lack of planning can lead to chaos, and how taking action early safeguards your business, your legacy, and your peace of mind.

Imagine a scenario that unfortunately happens far too often: A long-time business owner faces an unforeseen crisis. One real examples involved a 75-year-old entrepreneur who fell ill and passed away suddenly, without any succession plan. His family was left answering his business phone and trying to fulfill orders within hours of his death. He had left “no instructions…no plans” for who would run his company in his absence. The result was a frantic scramble to piece together how to keep the operation going, relying on fragmented notes and hurried conversations in his final days. An expert described it as “the worst case” scenario. The business (a wholesale food distributor) and the family eventually got through the crisis, but not without immense stress and risk. Perhaps the most frustrating part is that, as advisors noted afterward, all of it was completely avoidable. It’s a cautionary tale: by the time this owner would have felt “ready” to retire on his own terms, it was far too late. Reality made the decision for him.

This Risk of Waiting for “Ready”

Stories like this underline the hard truth: if you wait until you’re ready to plan your exit, you may never get the chance to do it properly. Many entrepreneurs, especially founders of small or family-run businesses, fall in a trap of procrastination. They are caught up in day-to-day operations and assume tomorrow will resemble today. One advisor quipped that owners often think, “No one’s going to die, right?…I’m immortal“, as if believing nothing will ever take them away from their business. It’s a natural psychological defence, after all, it’s uncomfortable to imaging your business running without you. But as another expert bluntly put it, “Face it – a day will come when you’re no longer in charge“. Every tenure ends eventually, whether by choice, by age, or by unexpected events.

When that day comes, not having a plan can be devastating. Without a succession plan (a roadmap for who will take over and how), a business can stumble badly. There are countless cases of families torn apart by disputes because the owner never clarified who would inherit or lead the company. Neglected businesses can flounder or fail while heirs or partners bicker over control. In extreme instances, if no successor is designated at all, the fate of the company could end up in legal limbo or even under court supervision. For the business itself, the lack of preparation often means a loss of value. Buyers shy away from a company that depends entirely on one person, or one that doesn’t have its financial house in order. As consultant Marc Emmer warns, “The window for proactive planning is short. Waiting until you’re “ready” is often too late.” In other words, by the time you feel ready to step back, you may have already missed the optimal moment to secure your company’s future on favorable terms.

Data on business exits confirms that many owners delay too long. A recent survey by the Exit Planning Institute found that over half of baby boomer business owners intend to leave their business within five years, yet only 27% had even completed a formal valuation of their company, and a mere 9% had any kind of formal estate or succession plan in place. Similarly, a 2025 study of private businesses showed that only 46% of owners have a formal succession plan in progress, and about 30% have no plan at all. These numbers reveal a huge gap between intentions and preparedness. Owners know an exit is approaching, but many put off the groundwork. The danger of this procrastination is clear: when transition time arrives (by choice or by chance), the business may not be ready.

Why do so many smart, dedicated business owners delay succession planning? Often, it’s simply because they’re busy. Running a company is all-consuming, and it’s easy to treat succession as a “later” project. As one advisor observed, small business owners are usually so occupied “doing the work” that they aren’t “thinking about the leadership aspect” of what comes next. People also avoid it because it can be emotional. Planning for someone else to take over feels like admitting mortality or giving up your “baby”. And indeed, letting go of control can be tough. However, not confronting these issues early can leave you with far worse outcomes. A business owner who waits until they must step down (due to a health issue, for example) loses the luxury of time to prepare successors or tidy up finances. Illness, accidents, or shifts in the market can happen with no warning. With a plan in place, your business won’t be left scrambling if something happens to you; without one, a sudden crisis can jeopardize everything you’ve built.

Succession Planning: Protecting Your Business and Legacy

Succession planning isn’t just about picking a successor the week before you retire. It’s about making your business “exit-ready” well in advance, so that it can thrive even when you step back. Think of it as an extension of good management and risk management. If done right, it protects your employees, your customers, and your legacy, as well as your financial future. In fact, creating a succession plan is as fundamental to running a business as making payroll or satisfying customers. It’s an essential part of stewardship.

One major benefit of planning early is that you remain in control of how the transition happens. Instead of decisions being made in a rush or under duress, you get to set the terms while you’re at the helm. You can decide who will lead, whether that’s a family member, a key employee, or an outside buyer, and you can shape the process to unfold on your timeline and according to your values. By contrast, if you leave succession decisions until the last minute, you may be forced into choices you wouldn’t have made otherwise (for example, a quick fire sale for the company, or passing the reins to someone ill-prepared). Starting early means you choose the narrative of your exit, not circumstances.

Another reason not to wait is that a good succession plan takes time to implement. Identifying a successor is just the first step; that successor likely needs mentoring and experience to effectively take over. If you plan to hand the business to a family member or promote an employee, it might require a couple of years of training, job-shadowing, or gradual leadership transitions so they can grow into the role. Even if you intend to sell the business to an outside party, you’ll want to spend time “grooming” the business itself to be buyer-ready. This can include documenting standard operating procedures, strengthening your management team, and building a customer base and revenue streams that are not solely dependent on you as the owner. Companies that have these elements in place are seen as more stable and valuable. In fact, businesses with clear succession plans and well-delegated leadership often command higher valuations, because a prospective buyer or investor sees a company that can run smoothly without the original owner as a lower risk. On the other hand, if everything in the business depends on the owner’s personal relationships and knowledge, buyers may view it as a risky proposition (or essentially “buying a job” that vanishes when you leave).

Consider asking yourself some tough but crucial questions:

• If I had to step away suddenly for a few months, could my business continue to operate effectively?
• Are my financial records and operations well-documented and “audit-ready” for someone to make sense of them?
• Have I identified who would take over key responsibilities?
• If a potential buyer or successor evaluated my business today, would they see a thriving enterprise with growth potential, or a company that is so dependent on me that it would struggle in my absence?

These reflections can be eye-opening. If your honest answers reveal gaps, that’s a sign to start addressing them now. The goal is not to alarm, but to motivate: a little preparation done now can dramatically improve your outcome later. As one succession expert put it, the businesses that fetch premium prices or survive generational transitions “aren’t accidents”. They’re built with documented processes, strong teams, [and] founders who aren’t afraid to step back”. In short, treat your business as an asset that must be able to stand on its own, whether or not you plan to leave soon.

Statistics underscore what’s at stake. Every year, over 200,000 small businesses are listed for sale, yet only about 30% of those businesses actually find a buyer. The rest, 70%, never manage to sell, often because they weren’t adequately prepared to attract a buyer or they waited too long and missed the market window. In many cases, the owners of those unsold businesses end up simply closing their doors, which can be a blow not only to the owner’s finances but to employees and the local community. Similarly, family businesses that lack a solid succession plan often don’t survive the transition to the next generation. Nearly two-thirds of family-owned businesses have no documented succession plan, and only 30% of family businesses make it to the second generation at all. These are sobering figures. The absence of a plan can mean the difference between your enterprise continuing as a legacy or ending with you.

The good news is that by planning ahead, you can beat the odds. Succession planning done right is essentially continuity planning. It asks “what if…” and puts safeguards in place so that whenever and however you exit, the business remains healthy. For example, if you start now, you can ensure that a sudden health issue won’t leave your team completely adrift. You can groom one or more potential leaders, gradually giving them more responsibility. You can work with financial advisors to get a realistic valuation and improve any financial weak spots (like too much debt or unreliable cashflow) before a sale is imminent. You can also consult with legal and tax advisors to structure any future deal in a way that protects your wealth and your company’s stability. None of these steps can be done overnight or in the middle of a crisis. They require that proactive mindset we’re encouraging. As a succession planning guide from one firm succinctly explained, “Don’t wait until you’re ready to leave” – start planning early so that your business is ready whenever the time comes. By doing so, you give yourself more options and reduce the stress on everyone involved.

Beyond the Exit: Preparing Yourself for What Comes Next

Prudent succession planning isn’t only about the company; it’s also about you, the owner, preparing for your next chapter. Stepping away from the business you built can be emotionally challenging. Entrepreneurs often have much of their identity and daily routine wrapped up in their companies. It’s not uncommon to hear a retired business owner say they felt a sense of loss after selling or handing over the reins. In fact, the Exit Planning Institute reports that a stunning 75-76% of business owners who sold their companies profoundly regretted the decision within a year. That regret usually isn’t because of the sale price or the new owner; it’s because the founders hadn’t prepared themselves for life after the business. They suddenly woke up with no place to channel their energy, no clear sense of purpose, and perhaps a loss of daily connection with colleagues and customers. It’s a bit like empty-nest syndrome, but for business owners – after years of being needed every day, they find themselves wondering, “What now?”.

To avoid that post-exit void, it’s important to plan for what you will do once you are no longer running the business. This is a deeply personal part of succession planning that often gets overlooked. Ask yourself: What do I look forward to after I exit? You might have passions or hobbies that fell by the wayside during your years of hard work. Maybe it’s traveling, spending more time with family, volunteering for a cause, writing a book, or even starting a new venture on a smaller scale. One executive coach shared that many owners struggle to “fathom what [they’d] do if [they] didn’t have [their] company to run each day,” so she had herself make a list of 20+ things unrelated to her business that she’d love to do in retirement. This kind of reflection can be healthy and exciting – it reminds you that there is still fulfilling life after stepping down, and it gives you goals to look forward to. Some owners chose to stay on in a limited role as a mentor or board member for the company, which can provide a gentle transition rather than an abrupt break. Others channel their entrepreneurial spirit into advising younger businesses or getting involved in community leadership. There’s no right or wrong answer except to have a plan for yourself.

By envisioning your post-exit life, you not only help prevent personal regret, but you can make better decisions about the transition itself. For example, if your dream is to travel extensively, you might structure the sale of your business in a way that gives you liquidity and freedom to roam. If you care deeply about preserving your company’s missions or taking care of longtime employees, you might be selective in finding a successor or buyer who shares those values, even if it means a slightly lower price. These considerations tie back into the succession plan as it’s about aligning the transition with your long-term personal goals and values, not just the financial traction. When owners have not thought this through, they sometimes end up with “seller’s remorse,” wishing they hadn’t sold or even attempting to “unretire.” If fact, many former owners without a plan for their next act end up buying another business or coming out of retirement simply because they feel bored or unfulfilled. Planning ahead can help you avoid that scenario by ensuring that when you exit your business, you’re moving toward something positive, not just away from something.

Start the Conversation Now

All of this might feel daunting, especially if you haven’t given succession or exit planning much though until now. The key thing to remember is that it’s never too early to start, but it can become too late if you keep postponing. The best time to start planning was probably yesterday; the second best time is today. And “planning” doesn’t mean you must announce your retirement or sell date now, it simply means taking steps to get ready and opening up dialogue. This could begin with a quiet conversation with a spouse, business partner, or trusted friend about your thoughts for the future. It could mean reaching out to a financial advisor or a succession planning expert to evaluate where you stand. If you have family involved in the business, it definitely means talking with them about their interests and expectations (avoiding those dangerous assumptions that often lead to family conflict). The Brown Brothers Harriman survey of private business owners noted that many owners are hesitant to discuss succession with the next generation, fearing difficult conversations, but holding back can actually hinder the successor’s preparedness and the alignment of values. Open communication, done gradually and thoughtfully, will help everyone be on the same page and reduce surprises.

Importantly, don’t think of succession planning as “giving up” your business. Think of it as insurance that your business will survive and thrive no matter what. It’s about creating options. When you have a solid plan, you might find you actually feel more confident taking a vacation or exploring other interests, knowing the company can run without you for a while. It can also give you leverage if an unexpected buyer comes along with an attractive offer. You’ll be better positioned to negotiate or to say yes on your terms because you’ve done the homework. As one business advisor put it, “the difference between a great business and a great exit isn’t luck, it’s preparation”. The owners who get the outcomes they want are usually the ones who planned ahead and built toward that exit over time.

In reflecting on your own business, try to identify one or two areas where you feel most vulnerable if you had to step away suddenly. Is it leadership succession? Is it that all the client relationships are in your head or your personal cell phone? Is it that the financial records are messy or you don’t have a clear sense of what the business is actually worth? Pick an area and start addressing it. Small steps, taken consistently, will build into a robust transition plan before you know it. Maybe this month you document standard operating procedures for critical tasks. Next month, you might sit down with a CPA to get a baseline valuation and see how to improve it. Over the next year, you might mentor a promising employee to take on more responsibilities. Each action will make your eventual exit (whenever it happens) smoother and more on your terms.

Finally, don’t hesitate to seek support and advice. Succession and exit planning often requires expertise in areas like law, finance, and tax strategy, as well as the human side of leaderships transition. You don’t have to navigate it alone. Consider assembling a team of trusted advisors. For example, your accountant, an attorney, and perhaps a certified exit panning advisor, who can guide you through creating a comprehensive plan. Even just having an initial consultation can clarify your thoughts. If you’re feeling unsure where to begin, reach out and start a conversation with professionals who specialize in this field, or with peers who have been through it. Often, just talking about your hopes and concerns for the future can kick-start the planning process in a meaningful way.

Final Thoughts!

In conclusion, waiting until you feel “ready” to plan your exit is a gamble that can put your business and legacy at risk. By contrast, starting the planning early is an empowering process. It lets you shape the future of the enterprise you’ve worked so hard to build, ensuring it can continue to prosper beyond your tenure. It also gives you the freedom to craft your own next chapter, rather than being caught off-guard by circumstances. Succession planning is not about anticipating your demise or rushing you out the door, it’s about being prepared whenever the next stage arrives, whether that’s next year or a decade from now. It’s an act of care for your business and everyone who depends on it, and an act of care for yourself and your family’s future. So take some time to reflect on what you want your “beyond the exit” story to look like. Then, take the first step and reach out for a conversation. It’s often said that the best gift you can give your business (and yourself) is a well-thought-out plan for the day you eventually move on. By not waiting until it’s too late, you’ll ensure that when the time comes, you can exit proudly, smoothly, and on your own terms, and set off toward whatever comes next with confidence.

References

• Emmer, Marc. “Business Owners: Is Your Exit Strategy Bulletproof?” LinkedIn, 2025.
• Teamshares. “Succession planning statistics in 2025: preserving a legacy.” Teamshares Resources, 2023.
• Friess, Steve. “What My Father’s Unexpected Death Taught Me About Business Succession Planning.” Gusto Talk Shop, Jan 2019.
• Mysogland, Edwin. “Emotional Considerations for Transitions.” Exit Planning Institute Blog, Apr 2018.
• Faust Hartnett, Judy. “Succession Remains Major Hurdle for Private Business Owners.” PLANADVISER, Nov 2025.
• Innovative Legacy Solutions. “Why You Need a Succession Plan—Even If You’re Not Ready to StepAway.” (Blog post, Mar 16, 2025).
• LinkedIn – The Whisper Group. Post by The Whisper Group (Dec 2025).