Trying new things and getting hurt will help you and your career

My face with a bandage over my chin
Ouch. Post-longboarding accident.
Audio recording of this article

In my home life, I’ve tried baking bread, playing in a band, singing, rock climbing, hiking, kayaking, gardening, water polo, and most recently trying to longboard. Professionally I have jumped headfirst into new frameworks, programming languages, presentations, speaking engagements, teaching an API workshop in the Caribbean, and new business-oriented roles. Most recently I started a completely new role in a new department doing vastly different work from the coding I had mostly been doing for the past 5 years. Here’s the thing though: I’m not an expert in any of these things. Rather, I’m someone that always wants to keep learning and trying something new. Some might call me a jack of all trades and master of none.

In a world where people need to pick between being a globe-trotting digital nomad and a 9–5 office worker, I think there is an alternative. Fulfillment can come from challenging yourself both in and out of your career, seeking discomfort, and setting lofty goals. The only downside to challenging yourself is that you will inevitably get hurt.

What kind of crazy person would subject themself to so many opportunities for failure? What is the benefit of doing it? Why try something even if you know you’re going to fail? Why play a game knowing you’re going to lose?

Jumping headfirst into something new is a learned skill, not a natural ability. It takes courage and self-confidence to accept that the results may not be ideal.

Failing fast is a tech mantra that attempts to mellow the feeling of failure. It tries to overcome the feeling that the results are not ideal. The reality is failure can hurt even with this mantra, and even the most well-intentioned constructive feedback can hurt too. Failing fast is a wall used to reduce this pain. In contrast, I believe that it’s precisely this pain that allows us to improve.

Photo by Thomas Tastet on Unsplash

The untested nature of Strapi and the fact it was in alpha didn’t make it suitable for a production environment. No matter how small or insignificant the application was that used it, the difficulty to harden this application and validate assumptions was not worth the time or money. Proceeding down this path was a bad idea. Quite frankly, people were shocked I hadn’t realized this earlier and I got a lot of criticism for it.

While this hurt, and definitely hurt my ego, it taught me a pertinent lesson on practicality. My loft ideas of trying to be on the leading front of technology didn’t fit with the practicality of budget, time, and risk appetite. This lesson helped me shape every future decision. We had to rewrite the application to include a less-than-ideal solution that wouldn’t match the functionality Strapi provided, but I would be able to deliver it.

“you can’t make an omlette without breaking a few eggs” — François de Charette

Photo by Marc Kleen on Unsplash

Now I know:

  1. Boarding is probably not for me. The risk does not equal the reward in my case.
  2. I’m more scared of needles than falling on a longboard so the thought of future stitches does not encourage me.
  3. What the visceral fat in my chin looks like from the open wound
  4. Stitches need to be done a few hours after the wound occurs to prevent scarring.
  5. If you’re thinking about stitches, you should probably get them.
  6. I have a new respect for the difficulty of skateboarding. I know why people enjoy the rush and being able to easily carry it with them everywhere.

For a 30 minute longboarding experience, I’d say that’s a lot of useful data.

Photo by Scott Graham on Unsplash

I was in for an uncomfortable ride.

Technology governance seemed like the furthest thing while still being within the tech industry. It would be high-level and not require any true technical knowledge. Governance is about analyzing the SOW, ensuring contractors and third-party vendors are meeting their obligations and keeping on budget and on time for upgrades and changes. It’s the near-invisible but ever-present penny-pinching role that involves a lot of extroverted qualities in a person. An equal limb in finance, technology, project management, and contracting.

From programming to leading fact-finding meetings, this was a stark contrast from sitting in front of a hot screen with headphones in listening to instrumental music and pumping out lines of code. The work is fluid and doesn’t follow convention. Although I guess it’s still in front of a hot screen.

I had a lot of early failures where I didn’t grasp the information I needed to present. Sometimes the directions I took were completely off-base as I was struggling to initially find a footing. These stumbles hurt and gave me a feeling of imposter syndrome. Presenting to a senior director and being told that I completely misunderstood the ask is a difficult conversation. But it’s precisely these failures and pain that motivated me to do better next time, and gave me the confidence to present my work next time.

Photo by Nick Fewings on Unsplash

I welcome the next risk with a curious mind and a tough skin.

Web software developer, leader, speaker and writer. Lover of horror games, craft beer, and rock climbing.

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