Successful people are very good at making things work. We solve problems, find another way, take on another responsibility, and keep going when other people might have stopped. Those qualities probably contributed to much of the success we’ve experienced, but they can also make it remarkably difficult to recognize when something has run its course.
We tend to assume that if something isn’t working, we should work harder. If we’re no longer excited about it, perhaps we need to recommit. If circumstances change, we look for a way to adapt. Persistence is something we admire in leaders, and rightly so. But I’ve learned something else over the years: something doesn’t have to be a failure for it to be finished. Remington understands this in a much simpler way.
Remi Knows How to Leave It
One of the commands Remi knows is “Leave it.” Like most dogs, she can become very interested in something she discovers on a walk. It might be something on the ground, an interesting smell, or something she has decided deserves further investigation. When I tell her to “leave it,” I’m not telling her that whatever caught her attention is bad. I’m simply telling her that we’re not going to stay there. We’re changing our focus and continuing in another direction.
Of course, knowing when to leave something behind isn’t always quite so simple for the rest of us. We are taught to persist. We celebrate determination and people who refuse to give up. As leaders, we’re encouraged to overcome obstacles and find another way when the first approach doesn’t work. Those are important qualities, and much of what I’ve accomplished in my own life has required persistence. But I’ve also learned that there are times when continuing isn’t necessarily the courageous choice. Sometimes it takes more courage to leave.
Not Everything We Leave Has Failed
We tend to associate walking away with failure. If we’ve invested years in a business, career, relationship, role, project, or particular way of working, leaving it can feel as though we’re somehow invalidating everything that came before. Sometimes we do need to leave because something genuinely isn’t working. We’ve tried different approaches, invested additional resources, given it more time, and finally have to acknowledge that continuing to pour energy into it isn’t going to change the outcome.
Other times, however, life changes around us. The thing we’re leaving may have worked beautifully. It may have mattered deeply and may even be something we would have preferred to keep. Yet it can no longer continue in the same way. That kind of leaving requires a very different kind of courage.
When Life Changed My Business
I understand that kind of decision personally. When my husband died, I didn’t just lose my husband. I also lost my business partner. We had built parts of our work together, and he brought his own knowledge, abilities, and skill sets to the business. After his death, I had decisions to make about what the business would look like going forward. There were services I could continue and things I could reshape, but there were also parts of the business that depended upon the expertise he brought to our partnership.
Those were things I needed to leave behind—not because they had failed or weren’t valuable, and certainly not because the years we had spent building them hadn’t mattered. I had to leave them because life had changed. Pretending everything could continue exactly as it had before wasn’t going to honor either the business we had built together or the life and business I now had to move forward with.
There was no clean line between a professional decision and a personal one. That’s often true of major transitions. We like to separate our businesses, careers, leadership roles, and personal lives into neat categories, but life doesn’t always cooperate. Sometimes the next chapter arrives before we’re ready for it, and the only way forward is to decide what can come with us.
Leaving Can Be Bittersweet
I think this is where conversations about “letting go” sometimes become too easy. We tell people to release what no longer serves them, move forward, reinvent themselves, and embrace what’s next. Those phrases sound wonderful until you’re the person standing in the middle of the transition. Leaving something behind can be the right decision and still hurt. You can know something is finished and still miss it. You can be excited about what you’re building next and still grieve what isn’t coming with you. You can feel confident in your decision and still occasionally wonder what life would have looked like if circumstances had been different.
Those feelings don’t necessarily mean you’ve made the wrong decision. Sometimes they simply mean that what you’re leaving mattered. Life is a journey, and some aspects of that journey are bittersweet.
The Question Isn’t Always “Can I Keep This Going?”
Last week, I wrote about knowing when to stop pulling. Leaders need to know when to inspire people toward a vision, when to push for results, and when continuing to pull harder isn’t creating movement. Eventually, however, another question appears: What deserves my energy now?
That’s a very different question from Can I make this work? Experienced, capable people can make an astonishing number of things work. We solve problems, compensate for weaknesses, take on another responsibility, and find ways around obstacles. Sometimes our very competence makes it difficult to leave something behind because we know that, technically, we could keep it going.
But being capable of continuing isn’t always a good enough reason to continue. There comes a point when leadership requires us to look honestly at where our time, attention, talent, and energy belong now—not where they belonged five or ten years ago. That can apply to a business model, a service, a leadership role, a professional identity, a responsibility we’ve carried for years, or even an old definition of success. The question isn’t simply whether we can continue carrying it. The question is whether it still belongs in the life we’re building.
You Don’t Have to Know Exactly What Replaces It
We often want certainty about what comes next before we’re willing to release what we already have. If I leave this role, what will I do instead? If I stop offering this service, where will the revenue come from? If I change the way I’ve always worked, what will my business look like? If I’m no longer this version of myself, who am I going to become?
Those are legitimate questions, but sometimes we know something is finished before we know exactly what will replace it. That space can be uncomfortable, but it’s also where possibility begins. You don’t always need a fully developed plan for the next chapter before acknowledging that something from the previous chapter no longer belongs there. Sometimes the first decision is simply: This doesn’t come with me.
Remi’s Takeaway
When I tell Remi to “leave it,” I’m not asking her to decide that whatever caught her attention was bad. I’m simply telling her that we’re not going to stay there. Perhaps there’s something useful in that for the rest of us.
Not everything we leave behind was a mistake. Not everything we stop doing was unsuccessful. And not every chapter has to end badly for us to recognize that it has ended. Sometimes honoring what was means having the courage not to pretend it can remain exactly as it was.
Recognize it. Leave it where it is. And keep moving.
Before You Go, I’m Curious…
I’ve been thinking about this as I’ve written this week’s lesson, and I’d genuinely like to know how other people see it.
Which is harder for you?
A — Knowing when to keep trying
B — Recognizing when it’s time to move on
You don’t have to explain your answer or tell me anything personal. Just A or B. I’m interested in seeing which answer is more common.
And if you’re currently facing a decision about something you’re not sure belongs in your next chapter, you’re welcome to message me privately. Sometimes the first step isn’t deciding what comes next. It’s simply acknowledging that something may need to change.