Properly dealing with failure will propel your personal and career development further than most efforts.

No one likes a complainer, but it’s doubly poor for your outlook and adjustment. Poor failure recovery is partly responsible for chronic depression, but even if you appear unaffected, you lose out on a valuable experience.

I like to deal with frustrations in my personal life with humor. If a situation is frustrating in a unique way, I can view the experience as a new story. If I’m lucky, it’s also a really funny story. A weird afternoon turns into something that I can use to bring joy.

But sometimes an unfortunate experience is just unfortunate. I accidentally overpaid. I was late for my flight. I delivered a project late. I was laid off.

For these I say “well, now I know”.

Sometimes the circumstance is a result of a mistake which I am now better prepared for. Sometimes it’s brought on by environmental factors that were never in my control. Still, I walk away with new information. I paid for a lesson.

#Failure case 1

One time I was flying out of Antalya, Turkey. I was to end up back in San Jose, but had a layover in Istanbul since the local airport only did domestic flights.

Despite being on the same airline, my connection placed me outside of the international airport, forcing me to go through immigration again. The first flight had also been delayed by an hour, causing me to miss my connecting flight and spend the next 16 hours in the airport.

My credit card, which was supposed to offer some financial protection, refused to do so. The new flight the airline booked me on was routed through New York where I would spend another 4 hours outside of JFK airport until workers started their day shifts at 6am.

All around this was frustrating. Enough for me not to forget much from those 2 days of travel. As frustrating as it was, there is some solace in the many learnings I made from this experience.

Firstly, I learned that connecting flights on the same airline do not guarantee any protection. I learned that connections can place you outside of the airport instead of inside it. Despite making it 15m before departure, I learned that the Istanbul airport is strict about boarding cut off times. I learned that making claims with your fancy expensive credit card for a circumstance they explicitly support is not trivial. I learned that it’s hard to know where your luggage is and you will get conflicting reports from workers at the same airport. I learned that you should preferably never have checked luggage and that you should stick AirTags in everything. I learned to prefer direct flights or longer layovers, but that short layovers are dangerous.

If someone asks me why I travel in a particular way, I have a story I am protecting against happening again. If a conversation starts around what might happen in such a circumstance, I have information to draw from.

#Failure case 2

Here’s something more career related.

I’ve been jumping around companies for a while. My current company has been my longest tenure and it’s finally clarified a lot of my negative experiences.

Two companies ago, I worked on a product team. I was dissatisfied with my work and dipped my toes into work from architecture teams such as Design Systems and Networking. I enjoyed these projects, so at my next company I went fully to an architecture team where this was my complete focus.

Yet again, I was frustrated. My team’s goals were not motivated by the health of the company but more internal politicking. We wanted teams to use the tools we produced, regardless of whether this resulted in a meaningful change in their development velocity.

I am now again in a product role and really enjoying it.

What I learned from “wasting” those years at different companies is that dev tooling draws engineers who feel unmotivated by the goals of their organization. Many companies create silos which fragment the goals within an org from the motivations of the company at large. If a product team has obvious and justifiable goals, it’s much easier to get excited by the work.

Startups get this for free, but some big companies can have this as well.

I also learned that doing the work outside of engineering (such as dealing with process) can be just as much fun as coding, provided the same conditions. If the problem is well defined and process change is a clear way to better solve it, it becomes fun to solve this way.

#The playbook

Some life lessons are more expensive than others. The distribution is not commonly fair, but it helps to deal with this fact in the best way you can.

Most engineering orgs are well aware of how they can learn from failure. Blameless post-mortems as an industry practice communicate that we can learn more from an analysis of the failure than placing responsibility on a party.

From an emotional perspective, this can still be hard to deal with.

In addition to “well, now I know”, I also like “okay, now what”.

You failed. Your circumstance is beyond repair. You are left in ruins. Okay, now what?

The bounce back and benefit from the failure is actualized the sooner you get over the emotional impact. The wallow and pity only stops the burning, but does nothing to heal the wound. This (your reaction) is obviously difficult to control, but not impossible.

Here is your failure playbook

1. You are miserable. Okay, now what?
2. What went wrong, could it have been avoided?
3. What was unique about this failure?
4. How can you use this information in the future?

You may find these questions difficult to answer, but try a bit harder and you’ll find them answerable.

Do you never worry?

”Would it help?”

– Bridge of Spies