ISSUE #025 | THE LEADERSHIP CONTRARIAN
Most leaders don't know they should get away to think and plan about their business.
Even fewer decide they should.
Even fewer still actually do it.
Last week I wrote about the larger Rhythms of Harvest, and how work and rest changing over the span of a year can teach leaders how to thrive over the long haul.
This week I want to talk about a different rhythm. A smaller one. A weekly, monthly, quarterly rhythm that determines whether your strategic time actually moves anything.
Strategic time is essential. Building a thriving company without it is almost impossible.
And yet, among the few who do take it, the session often gets squeezed into a slot. The moment it's over, the calendar starts screaming again, and very little actually changes.
Here's what very few leaders see:
Strategic time is one of the most important things you do. Strategic time without margin around it is one of the most wasted.
This last week, Kathryn and I traveled to spend a planning day with our friend and advisor Ryan, on his farm in the middle of Vermont farmland.
We had built the day around hard, honest questions. Where are we in this season of running Half a Bubble Out? What does maximizing our impact actually look like from here? What do we keep, what do we change, what is God inviting us into next?
That kind of conversation isn't a one-hour meeting. It isn't even a one-day meeting.
We've learned, slowly and at a real cost, that the conversation is only half the work. What you build before and after the conversation matters just as much.
When coaching clients tell me their planning offsites didn't work, I almost always find one of two things missing.
The biggest is structure. A loose agenda, a wandering day, a conversation that never landed in real decisions. That's a topic worth its own issue.
The second is margin. They built the offsite. They didn't build the margin around it. That's the one I want to address today.
Here's what good margin around strategic time looks like.
We added extra days at the front of the trip, not to escape each other, but to create space within our time together.
Not minutes. Not a couple of hours between meetings. A few days.
You can't run hard until the moment you walk into a strategy session and expect to think clearly. The mind is still solving the last problem on the last call. The shoulders are still up. The questions are still surface-level.
Breathing room lets the deeper questions rise. It's not optional. It's what makes the rest of the time work.
Your situation may be different. But for Kathryn and me, the front-end time does double work. We aren't just business partners, we're also married. Those days give us restoration as a couple and time to align as partners, in the business and in our marriage, before the strategic work begins.
You cannot do this work in the office.
The office is where the urgent lives. It's where every interruption knows where to find you.
Get away. Far enough that you can't easily get back.
A coach can make a real difference facilitating the day while bringing outside perspective on you and your company. But you don't need a coach for this to work. Partners or senior leadership can do it with you when you've built a good agenda.
And if you're going alone, a coach becomes more valuable, not less. There's no one else to push you past the obvious.
Kathryn and I usually do our strategic time on our own. But this particular trip was unusually significant, which is why we flew across the country to work with our friend Ryan.
This is the part most leaders skip.
After a hard day of analyzing and weighing and trying to find the gold in the middle of everything, you have to give the conversation time to settle.
We didn't run for the airport. We didn't jump back on the treadmill the next morning. We gave the big conversations a couple of days to marinate.
You know what happens when you skip this?
You have the great offsite. You drive home full of clarity. By Friday, the inbox has reclaimed you. By Monday, you're not sure what you actually decided. By Wednesday, the insight is gone.
The marination isn't optional either. It's the part that lets the work become real.
I've done this myself. Built the offsite. Skipped the margin. Wondered why the breakthrough didn't stick.
And I've sat with countless leaders watching the same pattern play out, leaders who want to grow their company and themselves and have figured out they can't do one without the other.
The block on the calendar isn't the problem.
The problem is that most leaders aren't the master of their calendar. The calendar is the master of them.
Building margin around your strategic time is one of the few moves that actually breaks that hold.
It occurs to me that Jesus modeled this also.
He worked hard. He moved fast. And He repeatedly pulled away from the crowds, sometimes when there were still people waiting, sometimes when His closest companions didn't understand why.
He created the margin. Then He came back to the work with refocused energy and a clearer line to His mission.
The pattern isn't new. We've known about it and struggled with it for as long as we've been alive. And still, it's rare.
If you haven't gotten away in a long time - for you, for your business, for your marriage if you're married to your business partner - let this be a small nudge.
Plan to get away. To restore. To reflect. To plan.
And then build the margin around it. The breathing room before. The marination after.
For Kathryn and me, this trip proved it one more time. Without the breathing room before and the marination after, our day with Ryan would have produced a fraction of what it actually did.
Without that margin, strategic time is just another item on a busy calendar.
With it, strategic time becomes one of the most valuable things you'll do all year.
If this was helpful to you, email me and let me know.
Until next time,
Keep learning.
Keep growing.
And God bless,
Michael