There is no intrinsic value to being in a management, leadership, or even a founder role. It's really a shame that we have embraced this nonsense of uplifting and celebrating roles and titles over contributions and outcomes.

Nobody gives a shit if you are a director of engineering but they may well care very much if you solve their problem.

It's all vanity and ego run wild. The reality of business is that the only two things that actually matter are building shit and selling shit. This is how to easily differentiate between cost and profit centers and who is essential vs expendable in an organization.

You should only be driven to be a manager or director if your fundamental skillset is dealing with bullshit to enable other people to do value creating work by getting it out of their face.

If you think you are moving a bunch of JIRA tickets around you should take a hard look at what a legit engineering manager deals with. And then add in trying to resolve bullshit conflicts between grown ass men acting like children, talking people into getting involved with your high risk/low reward squad, forcing people to make a decision and start moving instead of arguing endlessly, having really uncomfortable conversations on the regular, firing people who have a mortgage and kids but have undeniably become a risk to the business even if you like hanging out with them, identifying, defining, and enforcing the processes and changes to keep everything from falling apart...

Your 25 years of experience don't necessarily have any impact on dealing with all that bullshit. You have to be fundamentally organized and passionate about driving others to succeed and absorbing damage so they don't have to in order to be a really legit manager. Unfortunately titles and position in the hierarchy has become irrationally coveted and rewarded in many organizations and people who are "senior" slide into these roles and fundamentally suck at it and create misery for their direct reports and commit unforced errors that put the entire business at risk because they don't know or really care what they are doing.

Do not envy and covet joining that squad.

The only thing that really matters is creating dope shit that people want to use and making money while you are doing it. What role you are playing in the organization isn't meaningful compared to whether or not it is winning or losing.

There are plenty of lone-wolf IC's out there pulling down ungodly amounts of money because they are just destroying it and the best way for them to create value is for everybody just to get the fuck out of the way.

Only become a manager if you can be an excellent one and crush it and don't think for a second that just because your former colleague slid into a lane when you didn't that he is succeeding and you are failing. He has a whole new problem now to make a bunch of other people successful and absord all their bullshit for himself to be successful. That's the job. You can only admire and envy him if and when he has crushed it and you are certain that you could have crushed it even harder and should have taken that shot.

And if that is where you are at start interviewing for management roles, grab one, and put the ball through the basket to prove it.

You haven't made a career mistake you are just ruminating on an insecure head trip. And fuck that, you don't need, want, or deserve to live that way.