Changing Legacy Mindsets

That Tim Guy
4 min readJun 21, 2022

“Your favorite song would be nothing but noise to Mozart”

Recently I was part of a large company with a large deployment of devices to specific businesses, these devices rarely changed once deployed on-prem to clients, some locations had as many as 4k. Kind of quasi-POS systems. They were just now, in 2022, getting rid of Flash. Figure that Steve Jobs sought to kill Flash over a decade ago, this was beyond reason, but also an opportunity to shine.

It wasn’t that they knew this was overdue, that was not anywhere near the issue. The company culture was to resist change and fight it when they didn’t want to understand current tech. Our problem was to hire me as an architect and never give me a single resource to manage or implement what I was coming up with. There were loads of architects, but no coders, at least none with modern skills and none I could get on a project to train or build what we needed a team to do. There was always a promise that at the end of the month (for nearly three months) the staff augmentation contractors were ready to start. I had just spent two years with 150 people under my UX/UI/FE org tree so I had an expectation of at least one person to teach.

I took the gig because it was an industry I had never dealt with before, so that was exciting enough to make 25% less pay than I should have been and hopefully get that corrected soon. Only fools have hope.

“Legacy cultures are cognitive dissonance”

My first sign of trouble was that everyone had been there 10–20 years. The 4-man architecture leadership team I was in had an average tenure of 7 years. They all had the “company mindset” where they would tell you that you are CompanyX and it was up to you to change the CompanyX culture. This was not possible by design. Ride it out for that sweet paycheck because you could be there for years doing nothing at all and each person made it possible for the other to do nothing since product only got updated when it absolutely had to and that was barely every 5 years for a new feature, not stack modernization.

At one point I had another new hire that was also disillusioned tell me “they don’t fire people, they make them leave, so you can go years doing nothing here”. That is reason enough to leave.

I have to make note that I had health and family issues too. The stress of being ineffective and having things weighing me down with no advancement actually made my blood pressure spike to Hypertension Stage 2 and ruined my sleep cycles. I had actual chest pains after meetings where nobody knew terms for anything and changed the scope on me out of sheer ignorance.

My ability to change legacy mindset checklist:

  1. Have agency to hire, fire, and change staff
  2. Work with peers that have ambition, or that have been there 5 years or less to avoid “gatekeepers”
  3. Ancient tech stacks mean fear of change, I’ll lose more arguments to atrophy than win
  4. Make sure I’m hired to acquire new skills not backfill legacy staff
  5. Don’t join FOMO that chases bleeding edge stacks, I decide, not a blog
  6. I get to be in planning and grooming, otherwise I’m “staff” not leadership
  7. Get paid for the title, not the role. If I’m costly, they’ll listen to me
  8. Don’t lose my cool, just leave. No need to argue with sticks in the mud

In one meeting I witnessed a creative go totally off the rails and tell everyone that he dealt with the clients more directly and more often than anyone else and that though their self-congratulatory ideas seemed good, they were ultimately stupid because he tried those a few times before and was ultimately shot down and told never to bring those ideas up again. I never knew I might feel like that guy in a few months.

So there I was, the June self-evaluation period I always have. It is a chance for me to look at my personal goals and how I felt about the company and as much as I like the people, I just could not get through to them. My health had gotten even worse and my friends that usually see me as a wild man actually got concerned for me.

I looked at what I had, where I had been and myself-worth and how much I respected my own career and choices I have made. I have made some bad exits too soon, but this is one that I feel like is the best one I have made in years and I almost immediately felt the stress lift.

I’m still working on my physical health, but my mental health is back to normal.



That Tim Guy

Coder, photog, stick-shifting, animal lover, gardener, cook, comedian, from 11746 living in 90210.