Epic Fails and Small Wins: What I've Learned So Far From My Career in Tech

By Publication of the original photo
attributed to Levy & fils per [2]
[Public domain or Public domain],
via Wikimedia Commons
In tech, the concept of agile development is a bit of a no brainer. Venture capitalists and start-up gurus encourage start-ups to "Fail fast." It's supposed to be a mantra that encourages innovation, learning and agility.

Make something. Make mistakes. Learn. Make something better.

Last week, as I was reading Why We Fail, I took a few minutes to think about all of the fails I've experienced throughout my career; some mine, some I just witnessed. Having bounced around the tech sector for half my career and government for the other half, I can honestly say that I have experienced some incredible failures. Here are just a few:

That time the start-up went under because shiny thing!

The first start-up I ever worked for ran out of money 18 months after I arrived. Mostly because the owner was too forward-thinking, and way ahead of his time. He got bored doing today's work, preferring to work on really innovative stuff that was far ahead of its time. (Read: we couldn't sell it because no one was ready for it yet.) Watching them run out of money taught me that the boring work often pays the bills. While the shiny stuff leads to innovation, fun and eventual demise if you don't keep up the churn to pay for it.

That time I fired myself from my job (but kept working there)

"You're going to be the sh*t disturber." That's what they told me when they hired me. My job was to completely rethink how we were using our website to serve a particular segment of clients. Except that when the dev team started pushing back, the management wouldn't back me up. I could no longer do the job they hired me for because the dev lead told me not to talk to her team anymore. My whole team felt the tension. So I proposed a completely different job, one where I wouldn't have to interact with the dev team, but where I could still be useful. Essentially firing myself from my position. My manager never talked to me face to face again for the rest of my contract. Being abandoned by my leadership taught me that it's ok to stop and say, "This isn't working". Some people will view it as weakness (aka my manager) but your sanity and the greater good are more important in the long run.

That time we used tech that was a little too bleeding edge (for some)

I ran an international webcast (with optional teleconference), and some of our clients were just not set up to watch streaming video (Hey, it was 2000). Immediately after the webcast ended, the most glorious email arrived in my inbox, full of 14 point red bold text, essentially yelling at me (the most junior person on the team) for what turned out to be a whole lot of PEBCAK and network issues. I was freaked right out. Everyone ran over to check out what getting yelled at by email even looked like! (Again, 2000) We'd taken the bleeding edge approach, using tech just outside the realm of some stakeholders' understanding. This experience taught me that pushing the boundaries of people's comfort zones will generate some pretty visceral reactions; people fear the new. It also taught me that perceptions about success or failure can differ widely within groups (i.e. Comms considered that a major coup; while customer relations thought it was too much, too soon for their clients - hence the nastygram.)

That time the project I was on went off the rails and we got sued

This was a major we-said, they-said situation: We documented the requirements, we felt they kept changing the scope, they felt that we never delivered. It was all true to some extent. In the end, they sued the company for breach of contract. It was disruptive, frustrating and downright scary, even just as a staff member. I mean, the lawsuit was about stuff I worked on! I never thought I would be in that situation. Watching the company get sued for work I did taught me that clients and leadership aren't always right, and sometimes they'll go big (i.e. suing) rather than admit fault.

That time my boss stole all my ideas and pawned them off as his own

No matter what I brought him, he would march into the VP's office and propose it as his idea. Every single time. So my colleague and I started playing a little game where he would mention my ideas to the VP in his bilats, then I would present them to my manager, who would then present them to the VP. It was a dirty little game, but the VP quickly learned who was valuable on his team. And I learned how to create opportunities to increase my visibility to the executive layer, even if it was just to get the credit for my work. 

That time I had a truly terrible performance appraisal

That year, I worked on multiple projects simultaneously, developed a community of practice, upsold a contract by 10 times, and had several weeks of "bench time" where I wasn't assigned to a project. And all they cared about were those weeks when I "wasn't billable". So I failed my performance evaluation. But I thought the year was a win overall. And that's when I learned that I use a different stick to measure my own performance and success, and it won't always match with the corporate culture. And I'm perfectly ok with that.

That time the boss hired someone so she wouldn't have to deal with me

I have a lot of ideas and I hate the status quo. Which probably (definitely) makes me exhausting to manage, especially for someone who just wants to maintain the status quo. So in this one job, the exec in charge got tired of me bringing idea after idea and installed someone between us to act as a buffer. Which worked out brilliantly, because she loved him. So off he went time and time again, presenting our ideas in his own way and usually getting her buy-in (and getting me credit for my contributions after she gave her approval ;) It was frustrating at first to have that buffer installed, but failing to get senior exec buy-in myself taught me that I won't always get support where I expect to get it, so I have to be creative and find it elsewhere, even if that means giving up some control.

That time I failed and can see that failure online every single day

You can't win every fight. And when some of those failures are on high-visibility projects, it means that you might be witness to the outcomes of those failures on a regular basis, for years to come. Some of my recent failed projects will be in my face for a very long time and I need to accept that I did what I could, but the outcome is not mine. (That's a bitter pill, I'll admit.)

That time I thought I was going crazy and failing all over the place

The business analyst on the project had documented the requirements from the proof of concept, and I just needed to update them for the pilot phase of development. But no matter how many docs I looked at, I just couldn't find anything useful. Did I understand what I was reading? Was I out of my element? What was I missing? After weeks of panicking quietly (Read: major impostor syndrome!) while my project manager grew more and more frustrated with me, I finally spoke up: the emperor had no requirements. It took a while to justify my position, but my project manager came to the realization as well. I learned that I need to speak up earlier when things are going off the rails to save myself and my project grief. And I also learned that sometimes people are really good at covering their tracks and delivering nothing in the process.

That time I couldn't find my footing

I was flailing. I couldn't integrate with the team: we worked so differently, I didn't know the subject matter, I didn't know anyone and didn't have a single friendly in the group. When I tried my approach, it blew up in my face. They gave me meaningless work to do. I called everyone I knew, looking for a way out. And then one day, I tried again. I just did my thing. And it worked: they saw the value and we were able to make progress on our project. And I realized that we would never be alike, and that's what would be the source of our success. And I learned that the cage I thought I was in is actually a cocoon, and if I spread my wings, I could create my own space and my own job.

I could go one for days...

Seriously, I could go on and on with more examples of my own failings and failings of those around me that taught me oh-so-much. Give it a try. You'll be amazed how much you've benefitted from your failures. Maybe even more than your successes.