Everything has an expiration Date: Overstaying your Welcome
I had an interesting conversation a few days over breakfast with a very sharp & capable Egyptian entrepreneur. He has built an incredible business but only after trying and failing badly a few times before he found this new business. Now they are a literal rocket ship with crazy good margins, unit economics and a massive new Series B to boot, impressive in this fundraising environment.
One of the big things we talked about was scaling and how this was the second major trigger point of failure in the tech startup world. You find yourself in the strange position of product market fit but yet you can’t keep up with the demand due to scaling issues. And everything you did before that worked so well doesn’t work anymore.
And this is usually the result of having people who were great last year but now just don’t have the skill set or experience to help you get to the next stage. This is pretty common and something pretty well understood in Silicon Valley. I discussed these different stages here: https://hardfork.substack.com/p/the-jungle-the-dirt-road-and-the
It’s actually quite important for anyone in the startup operating and investing world to understand. We all have an expiration date in the roles, companies and actual locations and places. Heck we have that in romantic relationships and marriage. Everything has an expiration date. You basically have to know when to quit.
I’ve said many times, in my career, I’ve always overstayed at most places by at least a year or two. My last year at Yahoo! & 500 Startups were awful experiences for me and pretty sure also for those I worked with. Needless political battles, and a lot of petty little things which I do take majority of responsibility for. Frankly, I was burned out, disillusioned and had stopped caring. Thus it’s easy to become unmotivated and not a little bit bitter.
Yet my deep fear of the unknown, the comfort of knowing the place and total lack of courage and laziness kept me there. “Better the devil you know than the one you don’t” as the old saying goes. This is what keeps people working in bad situations or places for decades. This is what keeps people in bad relationships for a long time, even a lifetime. Taking sh-t and indignities that no self respecting person ever should.
So how do you know when you are hitting your expiration date? A couple very obvious signs:
You stop learning. Where before you were learning a tremendous amount, you have stopped learning. Basically your learning curve has flattened. If you feel like you are the smartest person in the room, that’s a bad thing.
You stop caring and your quality of work goes down. Where before you worked a tremendous amount of hours and couldn’t wait to get to the office. Now you have a feeling of dread every Sunday night. You can’t wait for the weekend. The excitement and romance is gone!
You dislike, hate and don’t respect all the new senior people coming into the organization (they probably hated me too :). And you do everything to avoid interacting with them.
You stop believing in the mission. Or maybe you still believe but don’t think the organization is doing the right things to execute the mission. You literally stop caring.
If you are feeling all of these things, you need to get the F-ck out as soon as possible. You are wasting your energy, and maybe most importantly, your ultra precious time. Time, which is the only non-renewable resource we humans have. Time to learn new things and work on amazing new opportunities. Time with people you love and respect. Time to really LIVE.
Trust yourself and your abilities and make the move before it’s too late. Better to plan and initiate the change yourself than to have it inflicted on you.