The Art of Ending Things

Knowing when to leave or stop something and how to do it with grace

This week, I announced leaving a wonderful 10-year career. I did not HAVE to leave, but there was a point where I realized…I MUST. It became a matter of when and how not if.

I suppose many things are simply a matter of when, not if, and certainly how…if you zoom out to a large enough time frame. But many big decisions seem to exist in one to two-year phases, between when the idea is first entertained, when opportunities enter the picture, time to think and plan, when things “feel” like they are right for a move, and when the action is complete. We all experience these phases, but I’ve learned to really listen, see them, and make notes to help with eventual, related decisions.

In my previous post, How to Say No, I cover saying no to ourselves and others, but that is not only about saying no to something new. It also applies to when we should STOP doing something. This means effectively being able to decide to quit, leave, or end things before something forces you to do so.

As with many big decisions (and the way I like them to go), my departure was neither sudden nor unexpected, but rather a series of compounding events, thoughts, and dynamics that led me to this decision. And then additionally, a thoughtful plan to prepare, organize, communicate, and implement. We all find ourselves at crossroads, forks in the path, and moments of decision throughout our lives. It’s powerful to learn to get better at seeing the choices on the horizon and to build to it with grace and intentionality, or at least with the possibility of the future decision in mind.

I hope by sharing my most recent example, it will help you with future forks in the road. And while this is about a career choice, similar dynamics apply to other life decisions, moves, relationships, hiring decisions, and more.

The Compass.

I’ve always been driven by more of a compass than a roadmap. I am not the strategic careerist my resume would suggest that I am. Rather, I have a very strong north star: I help people realize I’m capable of more than they know, and I want to put that purpose to its highest and best use at any given time. It is a deep magnetic pull in a very specific direction. It points to that intersection of things that I’m good at, where there is both need and opportunity, and other elements - very in line with the concept of Ikigai. It is the foundation of my yes-filter and the motivator for opportunities I seed and create. It may shift a few degrees here and there over time, but the vector is consistent.

I also have a very strong veto muscle. I learn over time what I don’t want and absolutely will not do. That list is short in the early days, and lived experiences help it grow and become clear and resolute.

Principles and Guardrails.

I remind myself that I have permission to grow and change. I often reread my mantra:

Don’t forget where you came from, but don’t you dare ever let it solely define you. Your truth is in your roots, but your past is not your jail.

I also use these two “bumpers in my decision and growth bowling alley”, which I talk about a bit more in another post here.

1. If I don’t, the competition (or someone else will); it’s another version of “If not me, who? If not now, when?”

2. Just because I CAN do something, does not mean I SHOULD

These questions are about 1) motivation and urgency and 2) responsibility and thoughtfulness. They help guide not only what I say yes to, but also how I think about what I need to stop doing.

My path toward my north star then gets guided by these principles and guardrails. That get’s blended with other factors that lead to how I spend my time (or invest resources if this is a big company decision) such as who I work or partner with, what I do, the value I add, the value I receive, and analysis for the financial side of things and ROE (return on effort).

Opportunity Costs.

Another way to decide when to say no, to stop, or to leave is to consider what you are missing by staying and not changing. This is a helpful consideration in every area of life. Very often, things are “fine” or good or at least good enough, but that sounds a lot like mediocrity and my mind, and my mom taught me that I deserve “awesome” - whatever that may be or mean. So if I start to feel that this is not the highest and best use of my time, money, energy, or talents in any endeavor, then by staying, I’m doing a disservice to myself and others.

Possibilities.

I constantly keep my heart and mind open to possibilities for myself and others. I celebrate others’ successes, build relationships, and help others. This brings me closer to new possibilities that months or years later may lead to something interesting. These seeds of giving, kindness, and openness grow into gardens of opportunity over the years. Most of my greatest opportunities can be traced back to years worth of connections, projects, and relationships. These things I’ve grown into over the years then become the new possibilities, against which I compare how I’m spending my time today. Things that were a side project or special interest activity start to show the potential to become one of the main things tomorrow.

Reputation and Grace.

So many don’t go out as strong as they started. Whether that’s as a result of waiting too long to leave or stop, or not prioritizing the “how” of the change as much as the “what”. Yes, choices to change are about us as individuals, but our reputation and legacy are built by our impact on others. For my largest decisions to quit something, whether that was ending a company initiative, shutting down a project or business unit, or leaving a team or company, the way it was done always centered impact on the team, especially for communication and timing plan. A basic flow:

1. Personal communication to direct reports or stakeholders first. Do your best to not let people read about the change from outside sources. Individual calls or meetings for those closest, then group calls for the next ring out

2. Follow up with thoughtful written communication that answers what might be the most common questions - why, when, where, what next, etc.

3. Circle back with teams to see if there are unanswered questions

4. Be clear and don’t confuse. The faster you get on to the new normal, or the next thing, the better

5. Recognize others along the way - their time, their impact, and their role

Onward.

Looking in the rearview mirror is good once in a while, but looking forward and up is far more productive. Once you’ve stopped or ended something, make the most of what you are doing and honor those past experiences by being even better in the next endeavor.

Onward, indeed!