How do you know when it’s time to quit something and when to stick with it just a little longer? All of creativity—and life, it seems—is really just an attempt to answer this question.
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Do I keep working on this painting or scrap it?
Do I push through the messy middle and finish my novel or start the next one?
Do I move to Manhattan and try to become an actor or keep saving up for a few years?
When do I risk it all and start over, and when do I play it “safe”?
There are no easy answers to these questions, and no one can answer them for you. This is the hardest part, I think. It’s your life. Only you can make the hard choices, and only you have to live with the consequences.
It’s a little daunting. But the brave thing to do is to ask the question and never assume that just because you’ve always done something, you have to keep doing it. And don’t be afraid of the answers.
Just because you’ve always done something doesn’t mean you have to keep doing it.
I have always enjoyed trying new things but struggled to stick with them. Earlier in life, this was a hindrance to my success. Life can be rather difficult when you are constantly blowing things up and trying to reinvent yourself every other week.
But as I’ve progressed in my creative and entrepreneurial journey, I have found myself at these pivotal moments. They happen every few years, and the signs are usually pretty clear. I can either continue to stay on the path I’ve created or forge a new one. I never know what to do in these moments, but I know that I can’t drift. I must consciously decide what the next step is going to be.
Lately, every time I try something new, something that feels true to who I am, good things happen. So when I found myself running a relatively large conference for the foreseeable future and feeling stressed about it, I began to question if that’s what I should be doing.
As you may know by now, this year is the last year we’ll be hosting the Tribe Conference , a yearly gather for writers and creatives to help you build the audience your message deserves. This is the fifth and final year, and as of now, we have no plans for what’s next.
This was not an easy decision, killing a part of my business that generates six figures in revenue each year, an event that some say is the best thing that they’ve ever been a part of, but it was necessary. Here’s why.
Reason #1: Because it was time for something new
I like starting things, not running things. That’s been an important insight for me these past couple years. At times, I’ve struggled with the angst of running a business when I would rather be creating. It’s taken a lot of pain and struggle to get to a point where I feel like my work is designed the way I want. And what I realized through that process was this:
Before you can be true to yourself, you have to know yourself.
Something I’ve learned about myself is that once I build something, I get bored with it pretty easily. Since I have worked very hard to have a small staff and a pretty lean operation, it’s important that I don’t just keep starting things that I have to run. In other words, I constantly have to prune to make room for the next thing.
This is something you don’t really think about when you’re starting a business until you’re pretty far down the road, I think. If every year you write a new book, launch a new product, create a new thing, in addition to all the other things you have going on, many of which require maintenance on your part, you will eventually run out of time and energy.
You have one of two choices: get people to help you or start killing your creations.
Author and entrepreneur Dan Miller deals with this dilemma in an interesting way. Every year, he kills about fifteen percent of his business to make room for some new innovation. Dan, who considers himself a “creative thinker”, understands that he likes making things more than running them. Because he knows this about himself, he has given himself restraints so that he doesn’t grow too large of a team that will require too much of his time and energy, which would mean time away from his creative work.
So he has a simple solution: take a part of the business—whether it be a product, program, or event—and shelve it. Discontinue the operation of it or put it on autopilot. Remove it from your warehouse so that you can make “space” (both figuratively and sometimes literally) for the next thing. This is about fifteen percent of his business. He does it every year as a discipline to make room for what’s to come.
Similarly, songwriter and musician Derek Webb tries to lose about a third of his audience every year. Seriously. I heard him say this one time at a conference, and I loved it. As an artist, he always wants to be pushing the boundaries of what is expected of him. Putting himself out there on this edge risks losing some of his fanbase, but it also introduces him to new people, while keeping him interested and engaged in the work.
Whether it’s fifteen or thirty percent, the point is this: To do important and fulfilling work, we have to venture out beyond what is expected, beyond what we are even comfortable with, and explore new horizons.
What is wise about each of these approaches is that they’re not risking the majority of their businesses. They’re not throwing the baby out with the bathwater or giving up the whole farm in hopes of some new opportunity. They’re giving up a minor percentage to make room for the next thing.
To do important and fulfilling work, we have to venture out beyond what is expected, beyond what we are even comfortable with, and explore new horizons.
For me, Tribe Conference represents about ten percent of the income my business makes. Letting it go feels like a “tithe” of sorts.i don’t know what I’ll be doing next, and I like that. I want the old to die before the new can begin.
Reason #2: Because it started to feel like the status quo
Something I’ve noticed recently is everyone seems to have a conference of their own. My friend Pat Flynn just started one. Terry Weaver, who has been a faithful member of the Tribe community, has launched a great event called the Thing. Michael Hyatt is doing some really stellar events, as well. And Alli Worthington just brought back Blissdom.
All wonderful events, and I’m so glad they exist. But as I was seeing more and more people start conferences, I started to wonder if I wanted to be doing what everyone else was doing.
When we started Tribe, we started with a question:
“Can we do this?”
This is always the question that precedes creation. Can I pull this off? Will this work? Can I get away with doing X?
When we did, we were surprised. It felt like a fluke. So we decided to try again. At that first event, we got about forty percent of the attendees to immediately commit to next year.
The second year, it was the same dare but slightly different: “Can we do this again?”
And we did.
The third year, we realized we had something fairly stable that we could grow, so the question became:
“What do we want this to be?”
When we realized it wasn’t going to ever be huge, because that’s not what made it special, we focused on creating a stellar experience for 200-300 people who had a message they wanted to get out into the world.
The fourth year, which was this past year, the question was:
“Can I enjoy this for what it is?”
Seriously. It was completely selfish. Everyone told me how great it was, but I was constantly seeing everything that was wrong with it. And this past year, I just decided to enjoy something I’d created. It was wonderful.
And so that brings us to year 5, and the question has become:
“How do we end this well?”
If you don’t know the questions you’re asking about your creation, it might be worth asking, “Is this necessary?” When I looked at Tribe and considered doing it for another few years, I realized the purpose that it had served was fulfilled. It was done. I’m grateful for it. Just because you have something good doesn’t mean it needs to continue.
Reason #3: Because I didn’t want to keep doing it
Man. What a selfish thing to say. Why are you stopping this? “Because I want to.” When so many people enjoy something so much, and you don’t, isn’t it worth pushing through?
I certainly thought so. For years, in fact. I had this thought that Tribe might not be something we do for years, especially when ticket sales were slow and expenses were high. It just seemed like a lot of work for a guy who writes books and doesn’t know a lot about running a large-scale event.
So I keep plodding forward, guiltily questioning my own motivations, feeling terrible along the way for wondering about doing something else. I did my duty, though, with a smile on my face, and every year when hundreds of people came to Nashville and were transformed by the experience, I thought to myself, “Maybe I can do this one more year.”
But as the angst began to build, I confessed to a friend, “I don’t know how much longer I can do this.”
He said, “If you are asking the question, then you’ve already made the decision.”
Wow. He was right, and still it took me some time to come to grips with that reality. This thing that I had done for so long (at least that’s how it felt at the time) was going to need to end. I told my team about this last year and they said, “We know. That’s not a surprise.”
I was astounded. “Really? It’s a surprise to me!”
“Of course not,” they said. “You told us from the beginning that you only wanted to do this for five years.”
Wow. I had forgotten about that. Perhaps, part of me knew from the very beginning how long this would last and that it would one day have to end. And to think that the people around me saw this before I did.
If you’re struggling to make a decision about ending something, anything, it might be wise to ask a few friends how they see your situation. You might be surprised by what they say. I was.
Reason #4: Because most things end
One of the great paradoxes of business and success, I think, is the assumption that things should always be growing and that if something is working, it should continue.
When I announced from stage during the last session of the conference that Tribe would end in 2019, I heard audible cries of protest from the crowd. One person screamed, “Noooooo!!!”
The conference has become a tight-knit and intimate community. People’s lives have literally changed at our little weekend event hosted in an old stove factory. So of course, there is some fear of something like that going away. I certainly felt it.
When I stopped onstage to make this announcement, I was wracked with fear and guilt and doubt. But as soon as the words started coming out of my mouth, I knew it was the right thing to do, even when some people didn’t like it or understand.
However, at the end of the event, one guy—a pastor of a church—came up to and said, “Man, I get it. As someone who does the same damn thing week after week for fifty-two weeks a year, for decades, I get it.” He smiled at me, nodded, and walked away.
The truth is that everything eventually ends. Nothing lasts forever. One way or another, this all comes to a conclusion—with death, of course, being the final end. So what would life look like if we better understood that? If endings were not something we avoided but embraced?
In the case of Tribe Conference, it means that I’m really able to enjoy this creation, because I know it’s ephemeral. Everything is always fading. Entropy is always acting on us, and that’s not necessarily a sad thing. It forces us to appreciate what we have right now.
As a parent, I feel this with my kids. Every day, they’re a little different. I know they won’t be with me, as they are now, forever, and so I try to be aware that every moment is precious. Childhood for them is ending one day at a time. There is no stopping it. And because I know this, I can enjoy it.
May it be so with whatever creation you’re dealing with right now, with whatever thing you’re thinking of ending (and I’m sure there’s something). Understand that it already is ending. Have you embraced it? Have you resigned that this thing, like all things, is one going to end? If not, you are living in denial and perhaps not enjoying it as much as you could.
May you, as I am trying to, learn that all of this is inevitable and our only job is to let it end well.
Nothing is as it has been…
—The Head and the Heart
Grab your tickets for this year’s final Tribe Conference! We’ll be announcing speakers soon, but you can still get in on the early bird tickets and save! If you get your tickets this month, you’ll also get last year’s speaker videos for free! Click here to register today.