Embrace that a Career isn’t always Measured by Climbing the Technology Ladder

What if I’ve been thinking about my career all wrong up until this point? How can that even be possible? I consider myself to be making the turn. Heading into the back nine of this adventure. Does that mean that I’ve wasted the first 9 holes of my technology career? These are heavy questions to explore but ones that I needed to address as I grabbed that metaphorical snack and made my way to the 10th tee. I realized this one important thing. My career isn’t defined by how high up the technology ladder I climb, but by the story I tell through the canvas I’m painting. I believe that this notion of climbing the technology ladder isn’t the only way to measure success.

How did I get here?

I’ve written about my story a few times. If you want to get a bigger picture of who I am, here are some good starting points.

From a career perspective, I can say that up until about 6 months ago I was climbing the technology ladder to progress to what some describe as the pinnacle of technology success. Chief Technology Officer. I began writing software for money in 1997 when I started helping people build dynamic websites using Perl and CGI. By the way, that’s my second Perl reference this year.

I fell in love with making something from nothing. Essentially building an experience for users by bringing together different tools and techniques. People are often taken aback when I state that I don’t like computers. The hardware aspect of things of course. I tend to think of myself as an artist more than a builder of tooling. I didn’t make the brush or the canvas but I created the artwork.

But back to climbing the technology ladder. There I was climbing and climbing and looking back upon it, I don’t know why I was. And then 6 months ago I just decided I didn’t want to do that anymore.

Climbing the technology ladder

Now I’m not arrogant enough to think that everyone’s experiences are like mine, but I do believe there are some common threads to be pulled on. And those threads are what I want to explore. And then I want to leave you with some words of encouragement. Because let’s face it. Jobs are hard. Life is hard. And things aren’t slowing down or getting any easier. Those are just the facts right now.

Why was I climbing the technology ladder?

Some of these might seem obvious and some of them are going to be intensely personal but I hope that you find them to be relatable.

Because I was supposed to

Did you ever do anything that you felt like it was because “that’s the next step”? If someone asked me why are you taking on that director role? My answer would have been something like, well I’m a Manager now, so Director makes sense. It’s what I’m supposed to do.

That assertion would roll off of my tongue without me giving it any thought. And as soon as that Director title’s ink was dry, I was thinking about being a Vice President. At my core, I’m an achiever. I like to get things done, check them off my list, and move on. There’s an instant level of satisfaction from marking that thing off of my list.

But because I’m wired this way, was that healthy for me to do it? Maybe yes, maybe not. But the problem with just doing what I’m supposed to or hard-wired to do is that I wasn’t looking at the bigger picture. I wasn’t taking anything else into account when climbing the technology ladder, I just “took that next step”. I was just taking it.

So often in life, we are on auto-pilot. We climb to the 15,000 feet and flip the pre-programmed switch to take our life to our cruising altitude and we just go. And we go from destination to destination looking for that thing only to realize, it’s not here. Let’s get back to the skies.

Comfort and stability

As a provider for oneself or a family, there’s a strong pull to provide a certain quality of life. For me, I’ve never paid much attention to the neighbors. The fact that they have a pool or a nicer car just doesn’t cross my mind. It’s OK if it does yours and there’s nothing wrong with it. Where it gets sideways quickly is if you allow that to transition from noticing to becoming resentful of your situation.

But let’s face facts, the higher up you go when climbing the technology ladder the more dollars you stand to gain. And the more dollars, the more comfort you can provide. Well yes and no.

One thing I knew in my head but didn’t know in my heart was that the higher up the technology ladder one climbs, the more responsibility I took on. The broader the problems became and the types of problems I was solving weren’t the problems I was solving on the previous rung. It’s like each rung of the technology ladder came with its own set of new challenges and gauntlets.

So while I was able financially to provide more comfort, I was getting less comfortable. I was personally losing myself as I was in pursuit of providing better for those I love.

Because I didn’t know who I was

Now this one could be a book on its own but I’ll do my best to articulate it in a few paragraphs.

A few months back, I set out to introduce myself to the world. I did this by publicly sharing my core values and some insight into who I am. I was 44 at the time. How in the world did I get to 44 and not realize that a number of the jobs on my resume were taken because I was hopping from one frying pan to another frying pan without evaluating why I kept landing in hot oil?

As a leader who was climbing the technology ladder, I’ve taken plenty of personality and culture profiles. I know the following things about myself and knew them even before I filled out the surveys.

  • I’m a heavy learner. But only as it applies to using that knowledge to do something.
  • Achievement is high up on my list of priorities (hence the ladder)
  • I need frequent recharging because I am what I am all the time. I only have 1 version of me.
  • I like macro-level problems more than details. But when I find a detail I find interesting, I’m like a dog with a bone. Have you been paying attention to all of my Rust content?
  • I tend to be more introverted. I love people, but I refuel in private.
  • Creativity and individuality are important to me.

OK, so I knew all these attributes about myself, but why did I keep ending up in these frying pans? Because I never understood what was important to me at my core. I had never evaluated an organization and a role against my values. And I had never looked at those “non-negotiables” for me before. Like I’d never ship Lambdas in Python or TypeScript. Completely kidding there … but you get the point that knowing the things I wasn’t willing to give up and do was never part of the equation.

And what I didn’t realize at the time is every time I sacrificed even just a little of my core, it ended up eroding into my soul. I’m being serious there. So I kept jumping from place to place, climbing the technology ladder because I didn’t truly know who I was.

I didn’t have a why

This seems silly to state out loud but I do believe that if I’m feeling this, there are others of you out there that feel the same.

This is back to that auto-pilot statement I made earlier. But when I was climbing the technology ladder, I didn’t really focus on what the next rung would do for my why because I hadn’t thought about it holistically. Let me explain.

I knew that the move up would yield more money. But I didn’t realize that the move up would yield less time and more stress. Well, I did but I didn’t know by how much. So while I’m increasing comfort, I’m again decreasing availability at home. And my why has always been my home. I just never took my why into account when making decisions about climbing the technology ladder. Because again, I was just “taking that next step” and figuring it out as I went.

This lack of putting my why at the center of my decision process and helping guide my career was just lacking and needed to be addressed. I was suffering from not taking a holistic look at my career. For such a macro-level thinker, I was suffering from not seeing the forest from the trees.

It was important for me to take a step back and look at these reasons both individually and how they played off of each other. In a vacuum, they aren’t good, but combined they are destructive. I had reached this technical accomplishment that by any measure should be celebrated but in the process, I’d lost direct contact with what I loved to do and who I was doing it all for.

It’s OK to not be OK

People think that just because you’ve had the opportunity to be a CTO from climbing the technology ladder, you’ve got it all figured out. For me, I didn’t. The above reasons for why I was climbing the technology ladder highlight that. And guess what? It’s OK. I honestly hope I never have it all figured out. But in terms of what’s next?

I’m still here. I’m still breathing. I’ve got some fight left in me so to speak and I’m ready to take that next step as head to the 10th tee.

What if the ladder didn’t matter?

That brings me back to The Matrix’s “There is no spoon” type of reference. But seriously, if there was no ladder then what would there be? I propose that instead of climbing the technology ladder, I’m out here painting my career masterpiece. I also believe that I’m not the only one. Some of you are painting and don’t even know it yet.

There are going to be spots that show great technique, areas of great emotion, periods of deep introspection, and then just parts of the painting that are ho-hum (the auto-pilot). Life and my career aren’t perfect and there are no erasers. My career painting is going to have parts of it that are done on purpose and some things are just happy accidents. And all of those are just fine.

I’ve come to terms with the fact that a ladder doesn’t measure my progress.

And I’m also not measuring my progress by how much of the canvas I’m filling up either. The point isn’t to fill up the canvas because in my head the canvas is like Hermione Granger’s purse, it expands on demand. My canvas is sort of CanvasLess.

My canvas just gets added to as I have a new experience, project, or life event. It’s only complete when I stop painting.

Taking something away from this

If I could go back and share with myself 20 years ago, what would I tell me? What can I tell you that is reading this?

Find what you love

My dad used to always share with me. Do what you love and you’ll never work a day in your life. Chase that passion. For me, climbing the technology ladder wasn’t helping me dive into that passion.

I get it, so cliche. But here I am at 45, walking away from the top of the technology ladder to be a consultant who is sometimes working at his kitchen table, sometimes working from a coffee shop, but always being available for his wife and kids. Because those are my why. And when I look at what recharges me (because again, I need to recharge) it’s solving technical problems and helping people ship value.

Do you see how I tied that all together?

Accept that it’s hard

Just because I know what I love to do doesn’t mean I’m not going to have ups and downs. But embrace the pain. Embrace the suck. Because those downs will allow you to enjoy the highs.

And don’t rush for it to be over so you can get to the next high. Eventually that high will be the last high and this will all be over. If you truly do what you love, you’ll enjoy the journey more than the destination.

Dig into what you need

Find a way to dig into what you need from your career. Remember, those non-negotiables that will keep you from jumping from hot oil to more hot oil. This might even mean seeking some outside help.

I’m in no way too proud to tell you that my decision to stop climbing the technology ladder started when I engaged a professional to talk to about my career. It then gave me the motivation to begin seeking my peers and those who had mentored me along the way. Professionals are professionals for a reason. They can help you understand at a more foundational level who you are and what types of roles might be more satisfying for you.

I’d also encourage you to lean into those who know you personally and whom you trust. I believe wholeheartedly in 360-degree feedback. I have blind spots and gaining insights from my peers, friends, and family was invaluable as I more closely inspected those things that fundamentally fulfilled me.

And remember, If I had all the answers I wouldn’t have been in this position. So it’s OK to ask for help. Climbing the technology ladder wasn’t for me and I needed to know that that was OK.

Climbing the technology ladder might not be bad

Wait, I just spent all this time telling you about why climbing the technology ladder is bad! Actually I didn’t. I wrote this to share my personal experience with how I believe there are alternatives to the technology ladder. And for me, those alternatives are where I want to explore my value.

But the technology ladder isn’t inherently bad. Neither is money. Neither is public recognition. None of those things are bad at all and if they line up with your why and don’t violate your non-negotiables then I love that for you. And honestly, there are a lot of CTO positions out there filled with amazing people doing the hard work of guiding an organization from that chair.

My caution though to anyone wanting to hold that position is, to make sure it lines up with your why who you are, and what you value. If everything checks out and you love what you do, then you’ll be A-OK.

Wrapping Up

I’ve just made this huge transition in my personal and technical life and as a point of reflection wanted to share that climbing the technology ladder isn’t the only way to measure one’s career. I’m fully leaning into this notion that a career is not linear. It’s not black and white. It’s a messy and beautiful creation I am the creator of. The story isn’t happening to me but it’s happening because of me.

The same is true for you too. There’s nothing wrong with climbing the technology ladder but it may not be the right approach for you. Coming to this realization might even be liberating on some levels. When you discover you might not even be reaching your full potential as you pull yourself up rung by rung, just let go and embrace new measurements of success.

The biggest things I hope you take away from all of this are the following:

  1. Discovering your why is a huge part of your career.
  2. Figuring out who you are and what you won’t sacrifice will drive employment and projects that will keep you near what you love to do and work on.
  3. There will be highs and lows but if you enjoy the journey and keep orienting around your why, things will work out.
  4. It’s never too early or too late to follow your passion. You miss 100% of the shots you don’t take. And with every miss, you learn how to get better at taking those shots.

Keep at it!

Thanks for reading and happy building!

Published by Benjamen Pyle

Benjamen is a genuine and resourceful technology creator with over 20 years of hands-on software development, team building and leadership experience. His passion is enabling technology teams to be their best by bridging modern technical design with outstanding business problem-solving. Recognized as an AWS Community leader in the areas of Event-Driven and Serverless Architecture, he brings multiple years of pragmatic experience designing and operating modern cloud-native and containerized solutions. When Benjamen doesn't have his head in the clouds, he's either playing golf with his wife and 2 boys or they are outside with their 12 paws.