Career Deep Read
Nikki,
You're the person who figured out early that you could learn anything fast enough to be dangerous — and then spent years proving it in environments where nobody was going to hand you a title, a roadmap, or a safety net. That's your superpower and your trap, and I think you know both sides of it more than you let on.
Here's what I mean. You went from being a *user* of an app to co-running its product and support infrastructure. You launched a coffee subscription business out of what I'd guess was equal parts genuine enthusiasm and a restless need to build something that was *yours*. You've moved through roles that most people would see as lateral — support, product, QA, customer success — but you experience them as one continuous thread of "I'm the person who actually understands how this thing works, end to end." And you're right. You are that person. But there's a cost to being the one who sees the whole picture in companies that mostly need you to hold one frame.
**You've spent a long time being indispensable without being promoted in the way that reflects it.** The Gigwalk trajectory tells the whole story — you grew from community manager to dual-role product manager *and* support manager after a workforce reduction. That's not a promotion, that's the company realizing you'd hold it together because you always do. And you did. You probably felt proud and resentful in the same breath, and neither feeling fully won.
The AI pivot is real, and it's smart, but let me say what's actually underneath it: you're tired of being the "support person" in rooms where you're thinking at a product or systems level. The AI generalist framing is your attempt to finally *name* what you've always done — pattern recognition, process architecture, connecting dots across domains — in language the market currently respects. You're not jumping on a bandwagon. You're trying to get credit for how your brain has always worked.
But here's the tension you're sitting with right now: **you're in Kansas City, you're remote, you're mid-career in a market that worships founders and engineers, and you know your resume reads as "support" to anyone who skims it for five seconds.** That kills you a little. Because you've *been* the founder. You've *been* the product manager. You've built tools. You've saved companies six figures. And yet the story you have to tell is fragmented across small companies most people haven't heard of, and you're constantly doing the translation work of explaining why your path is an asset and not a series of accidents.
The escape room thing isn't just a fun fact — it's genuinely how you see yourself, and honestly how you operate. You walk into chaos, you find the pattern, you get out. What you're less comfortable with is sitting in rooms where the puzzle isn't solvable, where the answer is "wait" or "this isn't going to work and there's nothing clever enough to fix it." Patience with ambiguity that *you can't optimize* is probably the thing that costs you the most energy.
You studied Spanish, math, and music across two universities and didn't finish a traditional degree — or at least it's conspicuously unmentioned. That tells me you're someone who follows intellectual curiosity hard and fast, and has had to build credibility the long way around because of it. You don't regret the path. But there are moments — probably in interviews, probably when someone with fewer skills and a CS degree gets the role — where you feel the absence of that credential like a phantom limb.
**What's quietly remarkable about you is that you've never stopped building.** Not once. Even in "support" roles, you were engineering systems, creating tools, writing documentation that became the backbone of operations. You don't just occupy roles — you reshape them until they fit your actual capability. The problem is that this means you often outgrow positions without anyone around you noticing until you leave, and then suddenly three people are needed to replace you.
The thing you most need to hear, and probably already know: **you don't have a branding problem, you have a betting-on-yourself problem.** You've proven you can build, you can lead, you can learn anything. The coffee company, the QA tool, the AI workflows — these aren't side projects, they're evidence of someone who keeps almost stepping into a bigger identity and then taking another role where you're brilliant but underleveraged. The next chapter isn't about adding another skill or certification. It's about deciding you're done being the best-kept secret in every company you join.
You're closer to that decision than you've ever been. The AI wave is your window and you know it. Don't let the part of you that's comfortable being "the person behind the scenes who actually holds everything together" talk you out of walking through it.
Here's what I mean. You went from being a *user* of an app to co-running its product and support infrastructure. You launched a coffee subscription business out of what I'd guess was equal parts genuine enthusiasm and a restless need to build something that was *yours*. You've moved through roles that most people would see as lateral — support, product, QA, customer success — but you experience them as one continuous thread of "I'm the person who actually understands how this thing works, end to end." And you're right. You are that person. But there's a cost to being the one who sees the whole picture in companies that mostly need you to hold one frame.
**You've spent a long time being indispensable without being promoted in the way that reflects it.** The Gigwalk trajectory tells the whole story — you grew from community manager to dual-role product manager *and* support manager after a workforce reduction. That's not a promotion, that's the company realizing you'd hold it together because you always do. And you did. You probably felt proud and resentful in the same breath, and neither feeling fully won.
The AI pivot is real, and it's smart, but let me say what's actually underneath it: you're tired of being the "support person" in rooms where you're thinking at a product or systems level. The AI generalist framing is your attempt to finally *name* what you've always done — pattern recognition, process architecture, connecting dots across domains — in language the market currently respects. You're not jumping on a bandwagon. You're trying to get credit for how your brain has always worked.
But here's the tension you're sitting with right now: **you're in Kansas City, you're remote, you're mid-career in a market that worships founders and engineers, and you know your resume reads as "support" to anyone who skims it for five seconds.** That kills you a little. Because you've *been* the founder. You've *been* the product manager. You've built tools. You've saved companies six figures. And yet the story you have to tell is fragmented across small companies most people haven't heard of, and you're constantly doing the translation work of explaining why your path is an asset and not a series of accidents.
The escape room thing isn't just a fun fact — it's genuinely how you see yourself, and honestly how you operate. You walk into chaos, you find the pattern, you get out. What you're less comfortable with is sitting in rooms where the puzzle isn't solvable, where the answer is "wait" or "this isn't going to work and there's nothing clever enough to fix it." Patience with ambiguity that *you can't optimize* is probably the thing that costs you the most energy.
You studied Spanish, math, and music across two universities and didn't finish a traditional degree — or at least it's conspicuously unmentioned. That tells me you're someone who follows intellectual curiosity hard and fast, and has had to build credibility the long way around because of it. You don't regret the path. But there are moments — probably in interviews, probably when someone with fewer skills and a CS degree gets the role — where you feel the absence of that credential like a phantom limb.
**What's quietly remarkable about you is that you've never stopped building.** Not once. Even in "support" roles, you were engineering systems, creating tools, writing documentation that became the backbone of operations. You don't just occupy roles — you reshape them until they fit your actual capability. The problem is that this means you often outgrow positions without anyone around you noticing until you leave, and then suddenly three people are needed to replace you.
The thing you most need to hear, and probably already know: **you don't have a branding problem, you have a betting-on-yourself problem.** You've proven you can build, you can lead, you can learn anything. The coffee company, the QA tool, the AI workflows — these aren't side projects, they're evidence of someone who keeps almost stepping into a bigger identity and then taking another role where you're brilliant but underleveraged. The next chapter isn't about adding another skill or certification. It's about deciding you're done being the best-kept secret in every company you join.
You're closer to that decision than you've ever been. The AI wave is your window and you know it. Don't let the part of you that's comfortable being "the person behind the scenes who actually holds everything together" talk you out of walking through it.