Imposter Syndrome

It's with me for life

We all know what imposter syndrome is. We may all have suffered from it at some point. I know I did.

We may even know, rationally, that this isn’t a sensible thing. One good representation of this was from David Whittaker

Inside Safe

Yet despite this whenever I started a new job I was always worried that I wasn’t the right person for it; that I’d fail to deliver. I feared messing up and getting called out as being incompetent.

As I grew into the role and started to deliver products and saw how my work improved the company my confidence would grow and I would be more comfortable; “OK, I can do this job.”

Soft deliverables

This is great when there’s hard deliverables; something you can point to and say “I did this”. When you see people using the stuff you create. When you overhear people talking to each other about it.

But what do you do when your deliverables are less concrete? When you don’t build but influence, or direct; when you build strategy; when people ask you for advice and your answers can affect a multi-million dollar project.

That’s the situation I found myself in when I joined my last job. I’d moved from an engineering role to an Enterprise IT Architect role.

Now a good engineer (and I like to think I’m a good engineer) must also have architecture skills. The decisions that I was used to making pretty much only impacted my deliverables (the users of my products didn’t care about the internals, just the results). It helped I was mostly a sole-contributor of code and not part of a larger programming team so I could refactor as I learned about the solution.

But now? Umm. I was part of a team that was responsible for the security of a large company; one of the oldest, possibly the largest, fintech company in the US; one that handled almost half of all credit card transactions in the US; one that ran the largest debit card network in the US. If I advised teams wrong and we got compromised as a result… I didn’t want to think about the consequences.

As time went on I grew a bit more confident. I also encouraged the rest of the team to chat a lot on IM (we were distributed across the globe; I was the only one in my location). This chat group was for both random nonsense, griping at management, laughing at bad vendor presentations, and also a “help” resource; if I wasn’t sure about something then I could ask the team for their opinion.

But I didn’t have anything concrete I could point to; “I did this”.

Worse, as I got exposure to more parts of the company, I got the feeling I was annoying more and more people. I tried not to be a “no, you can’t do this” type person and tried to help them come to a good solution, but there are always problem teams.

I’ve been a blocker, more than once; I’ve demonstrated solutions had problems (one team leading to the CISO having words with a VP of another team); I’ve probably antagonized people. I know I’ve spent many a sleepless night worrying about meetings I’ve had, or were about to have, and how they could go better.

Self deception, self deprecation

Because of a lack of hard deliverables, I had no way of measuring myself.

Of course my year-end self evaluation was full of “I did this”, “I did that”, “I did the other” but these were just words.

I find it hard to accept praise. My boss said I was doing a good job. More words. Apparently the CISO was happy with my work (although I rarely spoke directly with him). Yet more words. Where was the objective truth?

So I would joke, downplay my contributions, say things like “I have opinions on lots of things; for some reason people want to listen to them”.

I really didn’t believe I was making things better; at best I was just stopping things getting worse.

Yet I get tributes

After I announced I was leaving the company and taking early retirement a number of people sent me messages (both in public and in private).

  • you have always been a voice of reason

  • I learned more from you than you realize. I truly appreciate everything you’ve done.

  • you and your brilliance will be greatly missed.

  • definitely learned a lot by just listening

  • will miss your expertise and guidance

  • I’ll miss having you around Stephen, always a pillar of reason and knowledge

  • I cannot think of a time when I disagreed with you at first, that by the end of the conversation you had not convinced me with facts and logic to move my position. THANK YOU FOR THAT! So few people here do that

  • I also want to thank you for the times I was able to work with you. At least for myself, as you had hoped, I did learn a lot. Not in as much around “facts” or raw technical knowledge (there was plenty of that) but how to look at a problem, problem solve and think it through to a solution (or as close as we could get to one

  • I will personally miss you and even though we don’t collaborate as much as I want lately (my fault, not yours), I somehow feel that part of “the good” of the company will now be missing.

  • i will miss the expertise and that you don’t succumb to a flashy dashboard and ask the hard questions

  • You will be missed - you are one of the wiser / smarter people here.

  • It’s sad that we couldn’t work more together. Really enjoyed that and it’s definitely a loss for the company.

  • So many thoughts, sadness for losing you as part of this team, gratitude for everything we’ve built here together, excited for you getting out of this place and hopefully enjoying a well-deserved retirement. I can’t imagine where I’d be without you, and am humbled everyday seeing how we’ve both learned and grown together the last (almost!) 10 years.

  • The legendary journey has been etched in history. It was a privilege to cross path with you.

  • Ha. I don’t mind you bugging me. You are at least well reasoned and thorough

There were also some tributes paid on the weekly leadership call, from SVPs and VPs. I didn’t record them verbatim, but they included things like

  • Helped me immensely

  • We wouldn’t be where we are without Stephen. He changed the way the cyber org works, and we created a whole new team because of him.


It wasn’t until I was leaving that I started to believe what people were saying; people I thought I had annoyed, people I had said “no” to, people who I thought just ignored me or saw my role as a speed bump stopping them working… all of them were giving me unsolicited praise.

Which really highlights the difference between my self evaluation and the reality. Right up until the end I wasn’t sure I was doing a good job, nor making things better.

In the long long distant past of usenet I had a signature:

      The truth is the truth, and opinion just opinion.  But what is what?
       My employer pays to ignore my opinions; you get to do it for free.

Maybe I was wrong and people did pay attention to my opinions after all!