Ostensibly, people dream about the day they can retire. They dream about days on the golf course or in the garden, time with the grandkids, traveling the world—all the rewards for the years of hard work and sacrifice. In reality, it’s not that easy for everyone—especially business owners. For the business owner, there’s more at stake. There’s legacy and a responsibility to the family’s future to consider. These variables can ratchet up the emotion in an already emotional decision. In my work as a family business consultant, I have witnessed family and closely held business leaders struggle to retire. The truth is it takes courage to retire. Many leaders get cold feet when it’s time to go, even if they’ve been planning for the succession for years. But knowing when to go is key. Everyone wants to go out on top (like Tom Brokaw) but many stay too long (ahem, Dan Rather). The key to getting it right is opening your mind to a wider view of the micro-considerations that will ultimately drive your decisions and timing around retirement. Start by asking yourself the following questions:
What was your vision when you started?
Now’s the time to look back and decide if you’ve done what you set out to do. If you have achieved your goals. If you have, why stay? And if you do want to stay, do you know why? Drawing two points on the map of your career will literally show you when it’s time to move on. Sure, there’s always more to do, but is it yours to do?
How do you define success?
There are a lot of ways to define success. Quantitative measures like revenue, profit and market share—the overall health of the business—are obviously important. Let’s assume for the purposes of this exercise that the company has met its expectations in this department. How about your qualitative measurements? Have you made a positive impact on your employees and clients?
What drives you today?
Is it the same as what drove you when you started? Do you have new reasons to continue in the business? Answering this question will help you determine what itch you’re really trying to scratch.
Now, the tougher questions…
Has your business outgrown you?
Things change fast. Markets, technology, people. It can be hard for business owners to upend decades of processes in favor of new technologies, but the fast march of technology slows for no business. Ask yourself, are you the best captain for this ship?
Do you trust your successor?
This can be a really tough one. In many cases, that successor may be your child. Not believing in your successor will obviously muddy your retirement plans. If this is the case, dig a little bit deeper as to why you lack confidence in them. How do others feel about the successor’s abilities to lead? Are you alone in these thoughts? Additionally, have you given your successor a chance to shine outside of your shadow? Sometimes a lack of faith is unfounded.
Are you a roadblock to the next generation?
Your successor will likely have a different style and approach than you—at least in some cases. That can be tough for leaders to accept as they transition out of the company. You’ve done things a certain way for a very long time, and it was successful. But you must give your successor room to implement and test their ideas. Give your successor more responsibility early in the succession process. It will tell you a lot.
What’s stopping you?
What are you really afraid of? If it’s none of the above questions, and it’s something deeper—lack of purpose, fear of change, mortality—get to the bottom of it and confront it. And finally…
What’s next?
What will you do with all of the freedom you dreamed about? Make a plan. What do you most enjoy in life? Focus on it and do it. For some, that might mean staying on with the company in a small capacity as a mentor or advisor. For others, that might mean sailing across the world. Whatever floats your boat.
