Experience Points

I’ve had a lot of conversations lately with people that are feeling stuck in their careers. They want more money and responsibility but don’t know how. Or even what.

I empathize with this feeling. I was so overwhelmed with what was possible earlier in my career that I also had my fair share of frustrations. I continue to!

And while I still have much to learn, my advice for anyone feeling stuck can usually be reduced to this: collect experience points. Optimize for learning. Raise your hand as fast as you can at every opportunity to learn and don’t look back. No amount of airport business books or formal education beats out earned experience.

Everybody should be ruthless about seeking out job opportunities based primarily on the capacity to learn there. Early in your career, you have no idea what you like and so you need to spend the majority of your time figuring out what there is to even like. In business, I’ve tried everything to varying degrees of depth. I’ve done work in marketing, sales, operations, leadership, HR/people, customer success, analytics, software, and product. I get to dabble with legal. I’ve been on teams, led teams, and built teams!

Much like a video game, your career has an indeterminate number of levels. Each level faces new challenges. Look at each day of work as an opportunity to learn, gain experience points along the way, and level up. Even the most menial tasks can be done easier and even more efficiently, given you care enough to figure out how.

And given you ask for it, as you level up you will continue to take on greater problems which will be commensurate with greater pay and responsibility.

If you’re still in a position where your financial obligations are low, I would accept nearly any role you can find working at a company with 5 to 30 people and see how you can maximize your impact. I don’t care if you are fixing laptops or building reports. As long as they’re growth-oriented and fast-paced, figure out how to do your work the best and become an absolute unit of a person to the company.

Smaller companies – particularly ones with a lot of entrepreneurial energy – are breeding grounds of opportunity. Once you figure out how to do your job the best, figure out how to work more closely with anyone making decisions or leading teams. Great leaders are constantly looking for hard workers who want to grow.

If you’re not in a position where you can easily pivot to a smaller company, or you quite enjoy what you do but want more: focus on broadening your exposure within the company. Continue to push yourself out of your comfort zone. People often forget that you don’t need to work as a marketer to learn marketing. You don’t need to work as a developer to learn about software. Ask your coworkers and managers stupid questions, they’re usually just happy to have someone that cares. Intimately understand your company and how you can/want to increase your impact.

Early on, don’t worry if the company is getting a deal on you. Don’t worry if your title is assistant, or if you’re making below market for your role. Don’t spend a single second stressing out because Susie got a promotion and you thought you or Kevin deserved it more. As long as you’re learning a crap ton, making a large impact, and otherwise garnishing experience points – it’s worth it. Your check will come in time.

Eventually, you’ll be ready to ask for a lot more money. And you’ll be damn worth it. You’ll be defeating final bosses while your coworkers are fighting low-level boars.

When I was just getting started, my desk used to be right outside my boss’s door. I remember early on being nervous when his door was shut because that meant I was probably going to have to field the rogue questions for him from the warehouse team. This meant a lot of guesswork, making a fool of myself, frantically searching for answers, falling flat on my face, and sometimes even pissing people off.

The silver lining turned out to be that I had to figure things out myself. Come to find out all along, that was a feature, not a bug! As time went on, I learned the answers to these questions. I learned about the root problem and then spent even more time solving them. I slowly became the guy people went to because I understood their problem and was motivated to fix it. As time went on, I was able to further empower my boss to work on higher-leverage tasks!

If you take away one thing from all of this, move your desk. I don’t necessarily mean literally, just figure out how you can take on the problems of those more senior to you. You might not have the answers to any of these problems, but in enough time, you will.

The bad news is that work will always be that. Work. The good news is that you’re in absolute control of what you’re capable of and every job is an opportunity to learn. Even transitory jobs should not be considered lost time. My short time as a product manager paid massive dividends in my career because I was able to leverage learnings about product/software development to what I do now. My time on the retail floor taught me an appreciation for consultative sales and client success.

Put simply, keep your eyes and ears open. Learn as much as you can. Try to broaden your exposure to every department in the company and insert yourself into places where you can help. Eventually, you’ll figure out what you like, and eventually, the right opportunity will come knocking. If you are good at what you do, you’ll continue to find yourself in more circles with other people who are even more talented.

While you’re working on earning experience points, the best thing you can do early on is to have a strong feedback loop for yourself. Illustratively, if you give a presentation, ask yourself or your peers what sucked about it. Then do it better the next time. Apply this to every single thing you do – from writing emails to selling protection plans – and eventually, you’ll be doing things that you’re unbelievably proud of.

Follow this thread of raising your hand at any and all opportunities for long enough, constantly striving to do better work, and you’ll build a massive moat of skills to apply to every job. And because you’re taking on new opportunities and helping your peers along the way, you’ll amass a network of talented people who will vouch for you. If you’re lucky, you’ll even be able to sometimes call them friends.

Then you’ll never need to submit your resume on another stupid job board again.

What is it about the hero always thinking that they’re immediately ready to slay the dragon terrorizing the town? Sure, they very well may have dreamed, ideated, and studied. But have they swung a sword at anything and failed? Have they earned any experience, or purely listened and hoped they’d be ready when the time came?

The way I like to look at it is this: much of early education and even your career is purely the tutorial. You learn how to hold your sword, toy around with a little magic, meet the shopkeep, and get your starter gear. You still need to figure out how you’ll get to the castle!

Then it’s up to you to slay the dragon.

Thanks for reading! If you liked this, I’d love to know!

By the way, Substack is tacking on some disclaimer to my newsletter asking readers to pledge a subscription if they like my writing. Please don’t pledge any money. I never asked for that and will never monetize. Treat yourself to some silly drink from Starbucks, you deserve it ;D

Wishing you and yours boundless experience points,

– Cullin