Admitting Where I Actually Am
I sat down to fill out a career development tracker, and it turned into a multi-day exercise identifying gaps I needed to own and stop blaming on circumstances I wasn't actively trying to change. I built the coaching process into a web app and also a CLI Skill (links at the bottom, it's all free) so anyone can run through the same exercise without having to piece it together from scratch.
The Worksheet
I had a Career Development Tracker to fill out at work. 1-year goals, 3-year goals, 5-year goals, 10-year goals, an "ultimate goal," and a skills section. It should have taken 30 minutes, an hour at the most. It took me 6+ hours over the course of a few days because I kept getting stuck on the honest answers, going deep on every nuance, and really exploring what I wanted in my career.
I used Claude to help me think through each section, and what started as a checkbox exercise turned into the most useful career conversation I've had with myself in a long time.
The tracker format is relatively simple. It has goals by time horizon, a skills inventory, actionable next steps with milestones, and some due dates to help with accountability. The hard part, well, I guess it not that hard, but the part I needed to do was being 100% honest about why I was stuck or at the very least felt stuck.
I'd been frustrated at work for a while, and I'd spent most of that time blaming the environment. The team wasn't being used strategically enough. Some of the systems I'd built weren't getting implemented. Leadership didn't seem to value the SE function the way I thought they should. That was the story I'd been telling myself, and parts of it were true to some extent, but I was leaving out the part where so much of it was on me. I hadn't demonstrated the value of those systems convincingly enough. I hadn't pushed hard enough or in the right ways. I hadn't been honest with myself about what I could actually control versus what I was using as an excuse to stay frustrated.
This exercise, the worksheet, it forced me to separate the frustration from the aspiration. "I'm unhappy where I am" sure as hell isn't a career goal. In fact, it's just a feeling and feelings don't fill in the 1, 3, 5, or 10-year-goal boxs. I had to figure out what I actually wanted, and that meant being honest about what was mine to own first.
Imposter Syndrome Is a Scapegoat (for me)
The 3 year goal was where things started to... unravel? I wrote down Head of Solutions Engineering at a Series B/C startup. Building an SE function, shaping product and GTM strategy, leading a team of people who care about the mission, still close to our customers and their problems. That's what I want.
Then I asked myself: "if that role showed up tomorrow, would I feel ready?"
Absolutely not, no. I'd feel like an imposter and interviewing for it would probably require stretching the truth about what I've actually accomplished.
The more I sat with that, the more I realized "imposter syndrome" wasn't the right label. Imposter syndrome is when you're qualified and don't believe it. You have the reps, the results, the track record, and your brain still tells you that you don't belong. That wasn't exactly my situation. I'd built KPI's, frameworks, compensation models, and deployed AI tooling to hundreds of users, but I'd never been in an environment where I could see those things tested and proven at scale. And a lot of that was because I hadn't sought out that environment or pushed myself to get there sooner.
In my eyes, thats not imposter syndrome. I think thats not having the proof yet and being honest about it, and the difference matters, because imposter syndrome you can work through with mindset shifts and confidence building. Not having the proof yet means you have to actually go get it, which is harder and much slower.
Most career advice would tell you to believe in yourself and go for it. Sometimes the honest answer is "I don't know yet, and I need the reps (aka more experience) before I will." Calling it imposter syndrome would have let me frame the gap as a feelings problem instead of an experience problem I needed to own and go solve.
Experience Is Not a Skill
The skills section of the tracker has two columns: skills you have and skills you want. When I started listing "desired skills," I would write things down like "pattern recognition for SE scaling decisions" and "scaling from $150M -> $350M."
The problem is that those aren't skills, but rather experiences, and the distinction changes a lot about how you think about your own development.
The test I ultimately landed on: can you deliberately practice this thing and get better at it through effort? If yes, it's a skill. If you need to be in a specific context or environment for it to happen, it's an experience. You can practice organizational design. You can study executive communication. You can't practice "being at a company that's growing 10x a year." That either happens to you, or it doesn't. Or said slightly differently, you can get better at curriculum design, but you can't practice working at a school district that actually funds its programs. Same logic... I think.
"Scaling teams through hypergrowth" shows up on most people leaders aspirational skills list, but it isn't a skill. The actual skills are capacity planning, process architecture, hiring strategy, org design, and so on. The experience is being at a company growing fast enough to test those skills at scale. If you think the experience IS the skill, you spend your career waiting around hoping to land at the right company. If you know the actual skills, you can start building them now regardless of where you sit. This might sound obvious, but somehow I was missing it, sigh.
This reframe was one of the most practical things that came out of the whole exercise. I went from a vague sense that I was missing something to a specific list of capabilities I can start developing immediately. The experience will come when it comes (to be clear, I have to be intentional about it and go seek it), but the skills are on me to start developing this very minute.
The Next Move
I could practice org design and study hiring strategy from anywhere. What I couldn't do from anywhere was prove I could execute them in a high-growth environment, and that meant something about my current situation had to change.
The career path I landed on required a decent-sized mental shift, and was the part I liked the least, which probably means it's the most honest.
I'm a Sr. Manager of Solutions Engineering who, at one point, had 15 direct reports spanning from NORAM, EMEA, and APAC. When I looked at my goals and my honest skills assessment side by side, one thing was clear: I'm not ready to be a Head of Sales Engineering who's leading people, who lead people. Not yet. I haven't had the reps in the right environment, and that's largely because I didn't put myself in one sooner. I stayed comfortable in a role where I wasn't growing in that capacity, and this was a choice I made, even if it didn't feel like one at the time.
I don't need a title change or a promotion. What I needed was an environment change and that meant the right move could be lateral (Sr. Manager at a company with strong SE leadership I can learn from) or it could mean "stepping back" to Manager at a growth-stage company if that's where the right mentorship and enterprise motion exists. Either way, the title matters far less than who I'm learning from and if the environment gives me a signal on whether my ideas actually hold up.
Once I stopped evaluating every potential move by title and comp and started evaluating them by what I'd actually learn, the options really opened up. But the ego part can still be hard. When you've spent years telling yourself you're a 'senior leader', being genuinely open to a step back feels like admitting I needed to grow in ways I haven't yet. And I do.
The Slashie
The tracker asked for a 10-year goal. I had originally written something along the lines of: "I'm not sure thinking this far out is overly beneficial for me."
While working through the exercise I came across the concept of a portfolio career, which I'd never heard of by name. It's the idea of combining an operating role with advisory work, angel investing, speaking, and consulting across multiple companies at the same time. Mark Roberge ran sales at HubSpot from startup through IPO, and now splits his time between venture capital, teaching at Harvard, and advising a dozen companies at once. No shot in hell I'm ever going to be allowed to teach todays youth at Harvard. However, the idea of taking decades of experience and applying it across a few things I care deeply about sounds like a good way to spend my final years working. People in the startup world sometimes call it being a "slashie" because your LinkedIn title becomes a pile of slashes: VP os SE / Advisor / Investor / Gym Rat.
I'd been doing a version of this for years. Running a solutions engineering team while raising capital for a startup on the side and helping execute an acquisition for another venture I am an LP at. I never had a word for it. Turns out the concept has been around since the 90's. What's the saying? You learn something new every day.
Once I had a name for it, the 10-year goal wasn't so hard to write down. I knew what I wanted, I just didn't have the language for it yet.
The Real Output
Yes, the tracker is filled out. The goals have been written, skills documented, and milestones have due dates. It reads professional and thoughtful and appropriately ambitious for a senior leader or a peer to read.
However, the real output was being honest with myself. About what I'd been blaming on the environment, that was actually on me. About calling something imposter syndrome when it was really a gap I needed to own. About confusing experiences I want with skills I need to build. About being okay with going backward before going forward.
A career worksheet forced me to stop vaguely knowing I was stuck and start being specific about why. Turns out the hard part was never figuring out where I want to go, but rather admitting where I actually am, and more importantly how I got there.
If you made it this far, and are curious as to what my "ultimate goal" ended up being; Build and lead teams that people look back on as career-defining experiences.
There's a web app where you go through the same structured conversation in a browser and get a Career Blueprint you can save and come back to over time. And there's a CLI skill for people who live in their terminal that runs the same process and writes a career-blueprint.md file when you're done (github.com/ryanxkh/career-coach-skill).
Web App: Career Blueprint
CLI Skill: npx skills add ryanxkh/career-coach-skill
Both run the same methodology under the hood with the same five phases, same pushback when your answers are vague, same skill-vs-experience distinction, and more. Tool choice doesn't really matter here, as the important part is being honest with yourself about where you actually are. I just made the tools to reduce friction and so you don't have much of an excuse to avoid that conversation =)
If you have any questions about the system prompt, the app, the process, or anything at all, just drop me a comment or shoot me a DM.
-Hodge