What's Success Feel Like?

Last week, I received a message on LinkedIn from someone I’ve never met. The subsequent conversations that I have had with them has been the impetus for this blog post. My thoughts aren’t quite fully-formed, but I wanted to get it down in writing so that I can continue to reflect on it and wrestle with some of the ideas that have emerged.

One line in their message really resonated with me and is the primary reason that I’m writing any of this.

The tech industry is pretty intimidating and I’m trying to get that first shot.

I’m not quite sure how it happened, but I’ve somehow managed to reach the stage of my career where I’ve “made it”. I’m not talking about this in some self-aggrandizing way to flex the jobs that I’ve had or the places I’ve gone. I’ve been pretty candid about my struggles navigating a new career and trying to make sense of the complexity of starting over.

I feel really green and as if each day is an instance that I need to lean on mentors and more senior members of my team. I forget that there are other folks who are at an even more embryonic stage of their own careers, and that I have the capacity (and honestly, I view it as something of a duty) to help them reach new heights.

Long before I transitioned to a career in tech, I spent some time working in educator roles. The more I reflect on the things that I like most about my work as a technical writer, the more I realize that it’s about the underlying desire to help people who are in need. The person in need may be a user who is completely lost in a poorly-documented product. Lately, it’s more often been someone looking for their first chance to prove their worth and to have an opportunity to make a livable income.

I’ve written and spoken extensively about how opportunities in technology organizations completely changed my life. I grew up without a ton of possessions and have had major setbacks that have taken years to overcome, but it doesn’t discount the fact that my story isn’t some rags-to-riches tale built upon me being grittier or harder working than everyone else. I was really fortunate to network with the right people at the right time and to have a lot of friends who were willing to vouch for me and my work ethic. These folks then appealed to their own networks to tell them about me. I’m finally in that same sort of position to help other people, and I am so grateful for it.

My value system around work and success was long predicated on what my paycheck looked like. I thought, “I’ll be successful when I’m finally making X amount.” It’s a broken model. Tons of monetary success doesn’t really mean much if the work itself (and, importantly, the individuals you have the opportunity to work with) doesn’t bring you some sort of fulfillment.

I’ve organized a few thoughts on finding fulfillment in work, and wanted to post them here in hopes that it will help others who are trying to find enjoyment in their careers, or like my new friend, get the first big opportunity in an entirely new realm.

Being bad at something doesn’t mean it can’t be fulfilling

I’m a perfectionist and I’ve always had to fight imposter syndrome, particularly in new roles, because I feel out of my depth. I probably stay in this stage longer than a lot of other high performers because of major depression and anxiety, but it’s imperative to remind myself that everyone feels out of their depth initially when they are trying something new. If you find that you’re in this same situation, give yourself a break.

Technology is tough. We work on really hard shit, typically on things that don’t exist publicly yet - things that live at the bleeding edge of technological advancement. It’s important that we give ourselves some grace during the learning period. We’re still figuring things out. Stretching your mind and your physical endurance and learning entirely new tasks will be accompanied by growing pains. Lean into that process, and fight the urge to get discouraged when something cannot be accomplished immediately. If you’re lucky, there will be folks in your network or your organization who want to help you succeed. You could very well be on the path to the most fulfilling work you’ve ever done.

Being good at something doesn’t mean it needs to be your career

I made this mistake early. I assumed that because I was good at something, it meant that I was “called” to do that type of work in perpetuity. Being very good at something can lead to boredom and stagnation (or a laundry list of other vices, but that’s for another post). Being challenged is important. I try to live by the rule that a minimum of 10% of the work that I do should feel foreign and beyond my current capability. There’s a subtle distinction here. I’m not calling for attempting work that truly feels impossible. You want this “stretching” work to feel like it’s out of reach. It’s a bit of a balancing act, and I have certainly been guilty of swinging too far in one direction where it gets overwhelming, but if you find the right balance, challenging work leads to growth in a way that leaning into your strengths never will.

Find what fulfills you by logging your work

I think there’s real power in logging all of the work that you do and sorting it based on difficulty and how emotionally or mentally draining you find it. Feeling run down? You’re probably doing work that you’re good at, but at too high of a volume. Feeling panicky? You likely took on too much work that’s beyond your current ability, and you’re too stretched. There is a sort of Goldilocks ratio of tasks that can be done well and efficiently to larger, more complex tasks that stretch your brain and unlock new capabilities.

I’m still surprised daily by the opportunities that have been afforded to me. A few short years ago, I thought that my career path had been derailed and that I wouldn’t likely find opportunities to be proud of the place that I work or the work that I am doing. Technology has unlocked so many doors for me, and opportunities like the one I have been given from my new friend on LinkedIn are a wonderful reminder that those of us who have found some modicum of stability or success owe it to ourselves and others to pay it forward. So many cool and powerful new products are being developed. We are stretching our understanding of our world and of the machines that we’ve created to make our lives easier. Here’s to not losing sight of the most important bit: being good to the people we are building the future with.