How to End Things Well: A Lesson on Pruning Your Life & Work

Everything ends eventually. How you do it is what counts. Learning the art of ending things well can mean the difference between staying stuck in a rut and living life fully alive.

How to End Things Well: A Lesson on Pruning Your Life & Work

Listen to the audio version of this essay here:

Recently while speaking, I heard myself say something I didn’t plan on sharing. I didn’t rehearse it, didn’t have it in my notes. It just came out: “Sometimes, the good has to end before the better can begin.”

It was in reference to this being the last year of a conference I’ve run for the past five years, but it meant a lot more than that. The past two years have been a season of personal and professional awakening for me in which I have realized what matters most to me, what I truly want, and what no longer works.

I’ve already shared why quitting things (including projects that are “working”) can be a necessary part of the creative process. I’ve talked at length on my experience of realizing that getting everything I wanted didn’t make me happy. I’ve even learned that letting go of my need to succeed is the only true way to feel fulfilled. In this article, however, I want to share the process of ending things well: how you know it’s time to end a season and how to do it.

That said, I’m no expert at this. In fact, I’m rather terrible at ending things. Oftentimes, I hang on to hope for too long, thinking that job or relationship or opportunity is somehow going to change. But something I’m learning to trust more these days is my intuition, that still small voice that speaks up when I’m headed in the right direction (or the wrong one).

So, let’s start with the why.

Why some things should end

In the book Necessary Endings, Henry Cloud says that endings are neither good nor bad; they’re necessary. Nothing lasts forever. You spend your life ending things until eventually even you expire. He writes, “Before the good can begin, the bad has to end.” But I want to take that one step further: Sometimes, the good has to end before the better can begin.

When I said this from stage at the final Tribe Conference, I was thinking about a lot of things: book projects and friendships and even places I’ve lived. Every good thing, at some point, has to end. And what happens when the “good” ends is that something better often comes along.

Sometimes, the good has to end before the better can begin

Jeff Goins

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When we let go of what was, we open up a space for what could be. This, I think, is an act of faith: to stop doing what other people may consider “good” or worthwhile and do something else, something that seems truer. In our world today, such unnecessary changes often seem foolish. And of course, they are. To quit “what’s working” in the hopes of achieving something else is a risk that could end in failure. But there really is no other way to find out than to try.

In my life, there have been many projects and people and even places I have quit that, in retrospect, could have continued a little longer. I could have learned another lesson or two, could have grown a bit more, but as far as I can remember, I don’t have any regrets about walking away from anything. I don’t regret quitting that job or ending that relationship, because something better always came along. The decision, even if it was forced on me, eventually led to something good.

As I consider certain changes in my life and work, I try to remember that sometimes the better can only begin after the good has ended. It’s a scary place to be, on this threshold of transformation, standing in the gap between who you are and what you could be. But isn’t that what living is all about? Certainly, that’s what art is all about.

So, what better thing are you being called into in this season? Consider the possibility that before that next good thing can begin, you must let go of the current “good” in your life. This is why we end things, or at least why we should: to open up new spaces for us to create a better way of being in the world.

When to quit and when to stick

But, you might be wondering, isn’t it bad to quit things? Shouldn’t we keep our commitments? Not necessarily.

Now, don’t get me wrong. I don’t want to be a flake, but sometimes the only way to succeed is to quit. Seth Godin wrote about this in The Dip in which he explains the world’s most successful people were quitters. He writes, “Quit or be exceptional. Average is for losers.” The adage “quitters never win” is nice to print on a bumper sticker, but it’s just not true. Winners quit all the time.

Winners quit all the time.

Jeff Goins

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If Bill Gates had never dropped out of college, there would be no Microsoft. If Nirvana had never ended, there would be no Foo Fighters. If Oprah had never quit The Oprah Winfrey Show, there would be no OWN or any number of other projects she has since started. Quitting is your first step before starting something new.

Of course, you don’t always need to quit things. In fact, some successes only come after you persevere, after you push through all the things that are not working. In his book, however, Godin distinguishes between two situations: what he calls the dip and the cul-de-sac.

The Dip is that necessary rough patch in any relationship, job, or project where everything gets harder and you have to push through it to get to the other side, like riding a bicycle downhill and now you’ve got to pedal up the next hill. It’s not going to be easy for a while, but soon, you’ll see what all this hard work was for. “Never quit something with great long-term potential just because you can’t deal with the stress of the moment,” he writes.

The cul-de-sac, on the other hand, is experiencing the same challenging situation over and over without getting anywhere. You go round and round without making progress. That’s when you know it’s time to quit. A rubric that I use when it comes to deciding if I should quit something or stick with it is to answer the following questions:

  • Question 1: Is this causing me to grow? Am I learning from this, or do I feel like I’m keep going round in circles? Does this experience tire me or excite me? Is there greatness on the other end of this current challenge or just more struggle?
  • Question 2: Does it bring me joy? Does it resonate deeply with me? Do I, at some intuitive level, just know that it’s right? It doesn’t mean there isn’t difficulty and pain, but can I honestly say that love is the thing that is guiding my decisions here?
  • Question 3: Is there still a need for this? Do people still want this? Is there a demand for it? Does it resonate with others? Or has it served its need and it’s time to move one.

Now, here’s the catch. After you ask yourself those questions, sit with the answers for a few minutes, then take a deep breath, wait for your mind to clear, and ask yourself one more:

“Is this what I want?”

Answer that question honestly and without apology, then move forward.

How I fired myself and started two new businesses

As I become more aware of what I want in life, I never know how to take the next step. It is not an epiphany, never has been. There is no lightbulb illuminated in my mind that says “move here” or “start this” or “build that” and all will be well. At best, it’s a fuzzy notion, some hazy mirage on the horizon I can barely see. Often, it’s not even that, just a feeling of angst, some sense that the life I’m living is too small for the one that “wants to be lived in me” as Parker Palmer so eloquently puts it.

Recently, this has meant doing less of the online marketing work I’ve done in the past—webinars and social media and online course launches—and more of the “core” work I’ve always wanted to do. Writing and speaking has always been what I wanted to do but have neglected out of fear. In some ways, it was easier to succeed at teaching people about writing than trying to do it myself.

So I decided to act boldly, to make a big move and fire myself from the business that was earning over a million dollars a year to start something new. How did I know this was the right move? I didn’t. But after going through the rubric above, I realized a few things:

  1. This no longer brought me joy. Of course, when I made a bunch of money in a weekend selling an online course, that felt good. It made me “happy,” but it was more of a thrill than a sense of deep contentment. It didn’t last.
  2. I felt like a fake. Whenever I did a webinar or taught a course, especially when it had anything to do with business or marketing, I did not feel like I was the most qualified person to talk on that subject. At first, I chalked this up to the impostor syndrome we all experience. But the more I did this kind of work, the more I felt like there was something better and deeper I should be doing.
  3. People were less interested. It was getting harder and harder to get the results that were once easy. Moreover, I was feeling less motivated to push through the Dip and keep going. This sort of resistance is natural in any kind of work, and this is not a good enough reason to quit something in itself, but for me, the flagging results and lack of energy I was experiencing were pretty good signs there was other work I ought to be doing.

So I stepped away from the online courses and product launches without knowing exactly what was next other than I wanted to be doing more creative work (i.e. writing and speaking). I didn’t know what would come next, but since I’d been saying “clarity comes with action” for years, it was time to take a dose of my own medicine.

What happened next amazed me:

  • Within a few short months, I started booking ghostwriting clients (something I had done on the side once and really enjoyed) and now have seven new clients, and they just keep coming!
  • I started consistently booking two speaking gigs per month (I have done this every month this year and should finish the year with at least twenty gigs done).
  • I began working on a new book for myself.

To be honest, this all felt pretty easy. Once I was clear on what I wanted, it all just came together. I may share more on that in another post, but for now, the point is that sometimes, you have to let go of the thing that worked for you in a previous season that no longer is working now. And it may be that the old has to die before you can even get a glimpse of the new.

Change is good (but often hard)

In his brilliant essay on “Self Reliance,” Ralph Waldo Emerson writes, “a foolish consistency is the hobgoblin of little minds.” When I fear that I’m being rash or impulsive with a decision, I think about that quote. Certainly, you can be foolish in your inconsistency, jumping from one opportunity to the next, quitting a relationship or job as soon as it gets hard. But you can slo be foolishly consistent, so stuck in your ways that you don’t learn anything.

Recently, someone asked what my definition of success was, and I said “Change.” I love change. I love transformation, even when it sometimes seems that things are getting worse. Because change is anything but boring, and I hate being bored. For better or worse, when we quit things, we learn. We grow. We change. And that’s always better than keeping things the same just for the sake of being consistent.

When we quit things: We learn. We grow. We change.

Jeff Goins

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What lies on the other side of this decision? You don’t know. No one knows. But I can guarantee you of one thing: you will learn. Even if the change ends up being a mistake, you will grow. And I don’t know about you, but I’d rather change something and learn than stay stuck in a situation that’s not what I wanted. As Herodotus once said: “It is better by noble boldness to run the risk of being subject to half of the evils we anticipate than to remain in cowardly listlessness for fear of what might happen.” The point is to never assume something is going to last forever and to consciously make the choice to reinvest in it or move on.

That said, there’s nothing wrong with staying the course a little longer. If you read this and realized that you needed to stick it out at that job for another year or that it’s not quite time to break up with your significant other, then great. But you might also realize that you’ve been sticking with something for too long and it’s time for it to end.

And it’s okay to be sad about an ending. Change is good but hard and often leads to painful situations that force us to grow. In some ways, that may be the point. So feel free to look back wistfully at the past, at what was, and appreciate it, thank it for what it gave you, and then move.

That’s what I’m doing with my conference. That’s what I’m doing with the business I started seven years ago and am currently changing. That’s what I’m doing with the person I once was. I am saying thank you, waving it goodbye, and welcoming the mystery of what’s to come. May you learn to do the same.

As we approach autumn, I am thinking about dying. Not death, but the process of letting go of one life to live another. What needs to die in me, I wonder, for some new thing to be born? And can I pause for a moment to observe the beauty in this death? Can I behold the brilliant red and orange hues of this ending in anticipation of some new “green” thing?

I hope so.

If you’re on a similar journey of becoming, I’d love to hear about it. Also, if you’re interested in bringing a piece of Tribe Conference home with you, the videos are now for sale from all previous years conferences. Visit to grab one or all of them.

What good thing did you quit, and what happened?