A while ago I wrote about what happens in a startup when a new event creates a wake-up call that makes founding engineers reevaluate their jobs. (It’s worth a read here.) Recently my wife and I had something happen that made us reevaluate a 25-year-old relationship.
These two bookends made me realize something larger: reevaluating all types of relationships – romantic, friendship, founders, business partnerships/ventures, and even countries. It’s a healthy and normal part of growing, getting older and, at times, wiser.
What Lies Ahead, I Have No Way of Knowing ... It's Time To Move On, It's Time to Get Going.
First World Problem
We had a close relationship with a local nonprofit for over a quarter of a century. By close I mean their first executive director lived rent free in a property we owned, we provided resources when they most needed it, I had sat on their board, and when I was a public official I listened carefully to their input and suggestions, and helped them where I could. When I couldn’t do something they requested I called them and let them know why. They did the same for me. When their next executive director took over (he had been the number 2 to the previous director), the relationship continued, but in hindsight was a bit more distant. About a year ago they hired their third executive director. He had none of the history with us. And here comes the wake-up call.
I called to ask for his support on an issue very important to us. The conversation ended with what I thought was “I’ll consider it.” I never heard back. So I was surprised (but shouldn’t have been) to discover a public letter from the nonprofit taking the opposite point of view. In the past when we disagreed I got a phone call or email that said, “We heard you, but here’s why we’re going to do X and Y.” This time, and the first time in 25 years, crickets — I heard nothing.
This wasn’t the end of the world and truly is a first world problem — but it was a wake-up call.
It took my wife and I about a week to take stock. We realized that the executive director didn’t do anything “wrong.” We weren’t “owed” a call. The new director was looking forward unencumbered by the past, while we were looking backwards at the 25-year relationship. Anything we did prior to his arrival obviously wasn’t on his radar. But it was a jarring change from how we interacted in the past.
We realized that our relationship had been on automatic pilot. Until then there was no reason to rethink it. Our original support was for work this nonprofit had been doing at the turn of this century. Now that was no longer their core mission. And as we thought deeper we applied the same lens to reevaluate other organizations we were supporting. And no surprise, many of their missions had also changed, or in many cases our own interests were now elsewhere.
Wake-up calls happen when you realize the contract you believed in isn’t shared anymore.
In the end, we are now supporting a new generation of non-profits.
But it reminded me about the bigger picture and the nature of relationships.
Wake-up calls happen when you realize the contract you believed in isn’t shared anymore.
Most Relationships Aren’t Forever
Almost everyone of us will go through breakups, either initiating them or being on the receiving end. Rather than thinking that equals failure, consider it a type of a life pivot.
Most of us grow up with a belief that “real” relationships are permanent. That if something mattered once, it should always matter in the same way. That longevity of a relationship alone equals success. It doesn’t. Permanence is comforting, but it isn’t how humans, markets, or institutions actually work. People travel with us for a while then the convoy reconfigures as life roles and needs change.
People change. Leadership changes (in business and countries). Priorities change. Incentives change. Organizations change. Sometimes you change and the other side doesn’t. Sometimes it’s the opposite. Sometimes both change, just not in the same direction. None of that automatically means anyone failed. It usually means growth happened.
Why People Move On
Moving on is often framed as disloyal or selfish. In practice, it’s usually neither. It’s reality finally catching up with a story you’ve been telling yourself. Common reasons:
The relationship was built for an earlier version of you.
At different stages of life we value different things: exploration, stability, achievement, meaning, time. A relationship can be good and still no longer fit.
The relationship was built for an earlier version of them.
This happens often to co-founders in startups. Skills needed in the early stages are no longer the ones needed to scale. One of you learns new skills while the other is heads down doing what they’ve always done.
The shared mission expires.
Some relationships may be temporal or transactional. They exist to accomplish something specific: raise kids, start a company, survive a hard period, launch a project. When the mission ends, you discover what remains. (For founders it’s often done-and-gone and off to the next one.)
The implicit contract changes.
Every relationship has unwritten rules: honesty, reciprocity, respect, no surprises, or, often fatal, a breach of trust. When those rules shift without discussion, friction appears.
Misalignment becomes chronic.
Often there isn’t a single disagreement. It’s a pattern. You keep explaining away discomfort and keep lowering expectations. Eventually you realize you’re managing a declining relationship. You start calculating the lost opportunity cost of not moving on.
The cost of staying rises.
As you get older, you become more aware that time is finite. You grow less willing to spend it on relationships that consistently drain more than they return.
People and institutions drift from your goals.
Individuals move toward comfort, status, and security. Organizations move toward new goals, new donors and shifting funding priorities, different metrics, and survival at all costs.. Sometimes that drift still matches you. Sometimes it doesn’t.
Lessons Learned
- A wake-up call is an event that shatters your current view of a relationship and forces you to reevaluate.
- You never know what will trigger a wake-up call.
- As we get older, we perceive time as more limited. We invest more in meaningful relationships and prune the rest. That doesn’t make us cynical, just more calibrated.
Time to reevaluate relationships when:
- Values no longer align
- You’re doing all the work
- There’s a breakdown of trust
- You would not be partnering with them if you met them today
Maturity isn’t loyalty to the past. It’s clarity about the present.
