Retirement lessons I learned as a former community organizer


5 months ago, I announced my retirement from Tampa Devs, a 2000+ member community organization I built from the ground up.

Tampa Devs has grown up all on it's own now. In a way that is different than my original vision. But I'm proud of what it has become, and that it has outgrown the need for me.

I've learned many lessons along the way. I'm writing this blog post to share some of the things I would have told myself prior to stepping down

Here are those things:

Founder's Syndrome is real

Founder's syndrome is the desire to "hold on" to that feeling of awesomeness and power at being known as "the guy who started that awesome thing". You practically get worshipped, asked for advice all the time because people seek your guidance, and people get super excited when you just walk in the room.

Letting go of something like this sounds terrible on paper. Why would anyone give up something like that?

If you get overly attached to this idea, this notion you will eventually forget what it means to be humble. You won't adapt or change, and get into a comfort zone because it's the easy way out - and eventually you'll go into a one step road to burnout/complacency - but only after you've destroyed everything you built

One thing I've learned in past leadership positions is you have to make room for others to step in. You don't ever want someone who you want to take over to say "Don't worry we can ask Vincent" or "I can't do things my way because Vincent doesn't like it". Nobody will grow and things will crumble overtime this way

The other part of Founder's syndrome is you have to shift mindsets. Once an organization grows to a certain size, it needs a new set of rules, operational procedures, adminsitration automation toolsets, and many other things that seem overkill at first glance.

The easy way out is to never delegate and just do everything yourself - but that does no favors for anyone

Stepping down is like a breakup

I've spoken to people who have built and stepped away from startups they've built, or have been acquired, etc including experiencing what it means to step down

Stepping down is like a breakup - except it's one you initiate and the thing your breaking up with is your own sense of identity.

You lose a lot in this identity - the feeling of awesomeness in doing the thing you love, the people who could only see you as that "person who does awesome things" and nothing else, the connections, the control, and your sense of purpose.

This will inevitably cause some level of depression. It varies between person and how much time and energy you put into that thing you built, and how much it meant to you. It's best to accept it for what it is and move on

This includes putting away all the swag in a closet somewhere so you never see it again, and making great attempts to disable notifications coming through social media / emails etc about where the org is going


You have to let go

You have to let go of any notion of what the thing you created should or could be. If it burns to the ground the next day under new leadership - that's something you have to be okay with. If it ends up becoming extremely successful - be happy for it, but don't be overly attached to the successes.

Don't confuse successes that happened after your tenure as purely your own either. It's not a healthy mindset and will reduce the amount of motivation you have for building new things

Be aware of your influence on others

If you simply stand in a corner of a room where the new executive meetings are held, you will ultimately influence how things are being runned. Even if you stand there and do absolutely nothing

Your presence alone has a tremendous effect so it's best to keep your distance as much as possible - if your goal is for the org to run without your intervention and grow on it's own

This is the best in the long term. Do not initiate communication to new leadership, wait for them to ask you for help - and be short and cordial preferably in text or email

Be okay being absolutely nothing again

You will have to be nothing again. It's a humbling experience and one that teaches many lessons

This is the second time I've been down this path. The first time was as a video game streamer. This time it's a well known local organizer.

You become free of obligations and commitments from the org, and you can focus on new/bigger pursuits and goals you have

But that also takes time to cultivate. It's best not to talk much about what your true next goals are - you might self sabotage yourself in the process


Be prepared to lose people in your life

When you step down, you are no longer that "guy that does awesome things".

The one's that will be strongly against it are the ones who tell their friends "oh yeah I'm best buddies with the guy that does awesome things, I can hook you up"

It's the ones that reap all the benefits without doing any of the work that will try to dissuade you from stepping down.

This realization was shocking to me. I couldn't fathom the idea that someone other than me had a harder time accepting me stepping down than me myself.

Your biggest supporters when you first started are most likely going to be the ones who will be the biggest protestors to your stepping down

You will be asked "What's next?" a lot

You will need an answer prepared because this will be asked a lot. There is some level of high expectation of you that you will be moving onto bigger and better things

But that treadmill will never end. You will climb forever until you realize there's nothing at the top. It's the journey not the destination that matters

The easy way out is to just tell people you're on a sabbatical or working on your career. Something that does not have a definitive timeline

If your time doing "awesome things" was all high points, it's best to take things slow and be prepared for the coming lows

Eventually you will come back if for a bit

And people will see you differently. You'll be asked "Where have you been, nobody has heard anything from you".

And that's okay. That's normal. You also need to step away from social media, to give people time for them to accept this new reality and allow leadership to grow on it's own.

You will hear comments that people feel abandoned by the transition, as if you done some horrible thing. You have to do you first, but don't get frustrated - this is to some degree how some people say they miss the good old days under your leadership.

Some people will who you only slightly remember from University from 10 years ago will act like you are best friends - but you don't really remember how you know each other. Be courteous and nice. You still have a public persona to uphold - not for yourself, but because others look up to you

Others will tell you "Isn't it nice things are running smoothly without you needing to do anything?"

Then you realize that everything is okay. That's life

The org you started only seemed like it was everything because you were constantly bathing in the bubble you created.

Take a vacation in a different city where no one knows anything about you - and have a hard restart - it's well earned

Hi 👋

I'm Vincent Tang, a web developer specializing in modern Javascript. This website is my digital garden of notes on backend, frontend, and devops! I'm the founder of Tampa Devs and I also run a coding podcast called Code Chefs