At some point, we will all have to leave an organization. It might be a company, a nonprofit, an extracurricular, or something else. A lot of people, including myself, get very emotionally invested into the work we do. Leaving is almost always hard. What is even harder is leaving with a strong likelihood that your impact will revert, or seeing it revert before your very eyes. I unfortunately have experienced this multiple times, and I hope to share my lessons with others who may be in a similar situation.

How to Know When Your Time has Come

Everyone must leave an organization eventually. However, in the moment, that time can be hard to identify. Often times, but not always, this will be due to a misalignment between you and the organizational needs:

  1. Capability Misalignment: You do not have the skills required to contribute to the organization’s long term strategy
  2. Strategic Misalignment: You do not agree with (or do not want to engage in) the organization’s long term strategy
  3. Opportunity Misalignment: You would have to deny more valuable opportunities elsewhere if you remain a part of an organization
  4. Cultural Misalignment: You have difficulty engaging in an organization’s environment, such as tense relationships with others
  5. Externalities: Your choice to exit is a consequence of externalities, and may not be directly tied to your relationship with an organization

Any one of these is not necessarily better than the others in terms, and often times multiple factors may be at play. All of these also will require deep introspection in order to identify when they trigger.

Identifying when these take place requires a lot of introspection. Capability misalignment is particularly difficult to identify. It takes an incredible amount of humility for someone to identify a market shift, understand what needs to take place to capitalize on a market shift, and understand that they don’t have the skillset to lead an organization through said shift.

Example: Robotics

The first time I went through this process was with my high school robotics team. During my junior year of high school, we were forced into lockdown. I was the software lead (for three years) and co-captain (for two years), so I was deeply involved in leadership. I tried keeping robot development going during the early phases of the pandemic, but as the fall of my senior year rolled around, I realized that I had to pull away.

Externalities were the primary driver of my decision to pull back my senior year. If I had been able to remain on the team post-COVID, I could’ve continued to make technical contributions and push the ball forward. However, it was difficult to meet and engage with students, and I knew I would graduate before pandemic-era policies were lifted.

Opportunity Misalignment was a secondary driver for this decision. The time I had spent with the team trying to navigate the pandemic was hurting my college application process and my academic performance. The return on investment, especially given the externalities, were hard for me to justify.

Preparing to Leave

In order to leave sustainably, you want to spend time planning for the transition. Identify others who could replace your contributions, and who you trust to guide the organization in a positive direction. Work with them to train them on what needs to happen, and be candid.

Depending on their current role, they might not have as deep insights into what is going on as you do. Candid discussions about the reality of the position, organization, and environment could better equip them to better navigate their responsibilities. I have seen countless times where people wonder why a specific decision was made, either to realize the organizational factors that drove it (either for good or for bad).

Choose people who you trust, and make the best decisions you can with the information you have, but do not take too much personal responsibility for what they do. People change. People may have different motivations than what you perceived. If you try to hold yourself responsible (even in your own mind) for what they do, you will be disappointed.

Make a Clean Break

Once you decide to leave, make a clean break. If you hang around in the vicinity afterwards, you may be drawn back into the organization or feel regrets around your decisions. If you have friends within the organization, you can remain friends with them. But leave distance between that friendship and your relationship with the organization. I know someone who left a high school robotics team for college, and was still designing the robot three years later. This was a drain on the person and caused the team to not build a more sustainable training culture. The longer you wait to do a clean break after leaving an organization, the harder it becomes for you and the organization.

Clean breaks are much harder, but also much more important, for people who were very involved. The unfortunate reality is that things will change without you, and those changes could bother you. Decisions will be made that you may not fully understand or may disagree with. The organization may fall short of its potential. You may feel that you could’ve done a better job.

These boundaries are not about hurting the organization, it is about protecting yourself. Soft exits can work in some circumstances, but those circumstances are rare and there is a huge risk of the break becoming painful or never fully taking place. The clean break helps remove yourself from future changes that you don’t have control over.

What if?

There is one question that nobody can answer: what if?

What if I had decided to stay? What if I had chosen somebody else as a successor? What if we had identified a market shift earlier? What if we had made a different decision?

Every time that I have had to leave an organization, these what if questions are the single most difficult thing to deal with. The problem with what if questions is that every decision is made in a specific point in time, with a specific set of information, and will have unimaginable downstream effects (the Butterfly Effect).

Once you start asking what if, the cycle can be hard to stop. The way I have found around this problem is simply to make the best effort and best decisions I can at every step with the information and environment I have. If you consistently do what you think is right in the moment, then you can reasonably assume that you achieved the best outcome reasonable.

I wish that it was as easy as just saying to not worry about it. The unfortunate reality is that you likely will go through this process, regardless of what you decide to do. It is an unquestionably emotional process. A lot of people who have more logical tendencies can particularly struggle with this process. Looking with hindsight reveals a lot of things that weren’t obvious in the moment, and it is easy to then operate on the assumption that you should’ve seen something in the moment. But you didn’t.

Watching it Burn

The original title of this post was “Watching it Burn.” It was based on my experience watching my robotics team struggle to navigate the Coronavirus, and me experiencing too many driving factors. Thus, I watched everything I had built fall apart before my eyes, as I was still part of an organization.

Watching it burn will more commonly be experienced after a person leaves an organization if said organization fails to handle market shifts, or experience serious culture shifts (that in ones eyes are negative), it becomes easy to attribute organizational failures to themselves. This realization can start a very intense cycle of what if.

People want to leave an organization and have it thrive, but that is far from guaranteed. Once again, you have to ask yourself “did I do what I think was right at the time.” Did you make a best effort to make the path sustainable? Did you try to choose the right people, given what you knew about them at the time? People, organizations, environments, and markets all are constantly evolving. The second you leave, everything is out of your hands.

There are three results that may happen from this.

  1. The organization manages to succeed on the new direction
  2. The organization fails
  3. The organization experiences a temporary downturn, but later corrects

When I left my robotics team, I was very concerned that it would not be able to survive the Coronavirus. It did experience a downturn, but new adult support came in. They built on some of the things that I developed, and the team is more successful than it has ever been. This newfound success is their win, not mine. However, I played my small role, and I am grateful that things ended better than they could’ve. Even if the team completely collapsed, I did the best thing I could at every step, and it would’ve failed despite my attempts to save it.


Leaving an organization that you are emotionally invested in is difficult. However, identifying the reasons to leave when they happen, making the best decisions at each stage, and choosing a clean break will help reduce the impact of the departure for you. I have unfortunately had to go through this process many times, and likely will many more in the future, but reducing the pain and looking to the future will end up the best option for everyone.