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

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

am that person that is always unabashedly trying something new and more than frequently I’m exceedingly average at what I attempt. I’m not negging myself or trying to be humble. It’s just true.

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?

ake these failures as opportunities to grow and learn more. The learning curve for most skills ends up being this: the more talented you get, the more you realize how much more you have to learn. Often the ceiling is near-endless. At one point, we thought The Beatles was a revolutionary band that shook the core of society with its racey guitar riffs. Now we have some incredibly technical music that would have been unthinkable at the debut of The Beatles.

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.

Image for post
Image for post
Photo by Thomas Tastet on Unsplash

my own career as a tech lead, I sought to carve out my spot within a company. By bringing innovative practices and new technology to the table I thought I could instantly modernize despite not having a great deal of influence. Although often brand new technology is in beta or even alpha, like Strapi was when I discovered it, there is a big potential in early adoption. I searched its docs, looked over its open-source code, and was confident it would be a fantastic option for content management at any organization. I thought that if I spent the time to socialize it and integrate it into a project I was working on, that it might stand a chance. I went in with admittedly naive intentions.

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

Image for post
Image for post
Photo by Marc Kleen on Unsplash

the case of my recent longboarding (very much a skateboard but with large soft wheels and an elongated deck like the name implies) adventure, getting hurt was more literal than most of my other attempts. I had a fantastic, coasting ride for the first thirty minutes. It was freeing and I thought to myself at that moment “this is such a beautiful and easy way to get around, you can even carry the board anywhere! This is the way I’m getting around from now on”. Unfortunately for me, moments later there was a small rock on the street ready to trip me up. Just in front of my house, this little rock decided to ruin my day and bring my ride to a crashing halt. A lot of blood, scraped hands, busted up knees and two stitches to my chin later I came from the experience with a sour taste. It hadn’t gone my way in the end, but I did take away a lot from the experience.

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.

Image for post
Image for post
Photo by Scott Graham on Unsplash

oon after my longboard mishap, I started a new role at work. After 5 years of helping to lead a programming team, I decided to get out of my comfort zone and try business-oriented work. My previous role had certainly required me to present to large audiences, executives, create slide decks and speak plenty of business talk like synergize and blockchain. However, all the work I was presenting was a direct result of my skills. It was entirely dependant on myself and the small programming team I was working with. We didn’t have anyone else to rely on to get the work done.

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.

Image for post
Image for post
Photo by Nick Fewings on Unsplash

he conclusion isn’t a dainty one. You will get hurt, and you need to embrace it. Make sure these injuries don’t stop you from trying something else. Don’t let fear dictate your future. I, for one, will continue to try new things, and probably end up being very average at them and/or get hurt.

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.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store