u/Dark_Sky_Guy

Thought I was “done with PM”

After our last reorg I hit this point where I was sitting in my fourth meeting of the day thinking, “I cannot do this for another 10 years.”

Not even because the work was hard. I just felt weirdly drained all the time. Like my entire job had become chasing updates from people who ignored Slack until the second leadership asked for a status report.

I’d spend hours preparing pre-reads nobody read, then sit through meetings where we repeated the same conversation from last week while pretending it was progress.

I started telling myself I hated PM. Opened LinkedIn every night, looked at random jobs, fantasized about disappearing into some role where nobody invited me to meetings ever again.

But then one day an engineer messaged me saying the spec I wrote finally cleared up a months-long misunderstanding on their side, and I realized.. damn, I still like THAT part. I still like taking a messy situation and turning it into something people can actually move on. I still like talking to customers when it’s a real conversation and not some fake “relationship building” performance.

So I started paying attention to what specifically was making me miserable instead of throwing the whole career away in my head.

I quietly killed a bunch of meetings. Nobody died. I made people write down what we were deprioritizing before adding new “urgent” work and suddenly half the requests vanished. Funny how that works.

Around the same time I dumped possible next roles into a spreadsheet because my brain was all over the place. I even reread notes from this old coached career assessment I took, and one part stuck with me because it basically called me out for liking problem-solving but burning out when too much of my day turns into managing everyone else’s emotions and chaos. That felt uncomfortably accurate.

I think the biggest realization was that I don’t actually want out of product. I just don’t want to spend my life doing calendar diplomacy and begging adults to answer questions they already saw three days ago.

So now I’m looking at TPM/product ops/BA-ish roles and trying to figure out where the line is between “healthy collaboration” and “full-time babysitting.”

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u/Dark_Sky_Guy — 3 days ago

Torn between a comfy job and a scary-but-better offer.

So a year ago I had two job options in front of me and I completely froze over it.

Job A was the safe one. School office job I’d already been doing for 4 years. Easy routine, people I liked, decent benefits, low stress. I could basically do it on autopilot at that point. But I also had this awful feeling that if I stayed there much longer, I was going to wake up at 35 wondering how I got stuck.

Job B was a coordinator role tied to my degree. Better pay, hybrid, actual career path. Also way more responsibility, harder situations, new systems, new team, all of it. I kept bouncing between “don’t be stupid, keep the stable job” and “are you only staying because you’re scared you’ll fail at something harder?”

What finally calmed me down a little was forcing myself to stop treating it like this giant life-defining moment and just writing things out. I literally made a dumb document scoring both jobs on stuff like money, growth, stability, and how drained I thought I’d feel day to day. Once I saw the tradeoffs written down, it stopped feeling so emotional.

I also realized I was focusing way too much on job titles and not enough on what my actual days would feel like. I talked to a couple friends who know me well, did a few random personality tests like Coached, mostly because I was desperate to see if there was a pattern in the kind of work I kept leaning toward. The big thing I noticed was that I’m actually worse with boredom than stress. That hit me harder than I expected.

The other thing that weirdly helped was thinking about regret instead of fear. When I pictured myself failing at Job B after a year, it honestly bothered me less than picturing myself still sitting in the same office doing the same thing forever and complaining about it.

I ended up taking Job B. First month was rough. I felt dumb constantly and had a couple “why did I do this to myself” drives home. But a year later I’m glad I left. The old job still sounds tempting on bad days though lol.

Hope this helps those in a similar situation.

reddit.com
u/Dark_Sky_Guy — 12 days ago
▲ 0 r/Upwork

Last month a prospect basically told me, “AI can do like 80% of this already, so why am I paying human rates?” And honestly? I couldn’t even fully argue with them.

What changed for me wasn’t trying to defend the craft harder. It was realizing clients weren’t actually paying for “a person who can type/design/write fast.” They were paying for someone who could look at a messy situation and make decisions.

So now a lot of my projects start with a paid diagnosis call instead of me instantly building stuff. Half the value is just telling people what NOT to do. Clients get weirdly relieved when you narrow 14 possible directions down to 2 and explain the tradeoffs like a normal person.

I also started packaging the annoying operational stuff more explicitly. Stakeholder wrangling, QA, naming conventions, follow-ups after launch, fixing the random thing that breaks once real humans touch it. That’s the part AI still doesn’t magically absorb.

Funny enough, while I was rewriting my positioning, I realized my own LinkedIn summary sounded like every other freelancer on earth. I ended up tightening a bunch of the wording after running it through Resumeworded just to see where it still sounded vague or fluffy.

The weirdest part is that the more specific I got about boundaries and ownership, the less people pushed back on price. Before, I sold “deliverables.” Now it’s more like: “I will help you make fewer dumb decisions for the next few weeks.”

reddit.com
u/Dark_Sky_Guy — 15 days ago
▲ 1 r/Resume

I’ve been in sales for a while now (mostly SaaS), and I just went through another round of job hunting. Reading my old resume back and it honestly sounded like I was trying to impress someone instead of show how I actually sell lol.

It was all big wins, big numbers, “top performer,” all that. Looked nice, but it didn’t really say what I do day to day. And I think that’s why it wasn’t landing.

The stuff that finally started getting traction was way less flashy.

Instead of saying I “qualified leads,” I spelled out how I actually filtered them and how fast I got rid of bad ones. Like rejecting weak inbound within a day and protecting my calendar so I wasn’t wasting time on junk meetings.

Same with follow-ups. I used to just say I was persistent. Now I actually wrote out the sequence I use after a demo. What I send, when I send it, how I push for a decision. It feels almost too basic when you write it, but it reads way more real.

Speed was another one I didn’t think mattered until I wrote it down. I tracked how fast I respond to inbound and how that affected show rates. Again, nothing fancy, just numbers tied to behavior.

Even handling objections, I stopped writing “sold value” and just explained how I connect pricing back to something concrete for the buyer. Way less buzzwordy.

Also added a line about some simple docs I made for myself (discovery checklist, objection notes). Nothing groundbreaking, but it shows I’m not just winging it every call.

When I rewrote everything, I ran it through resumeworded just to sanity check it. Whole thing ended up feeling almost too plain compared to my old version, but that’s the one that started getting replies.

Curious what other people here have noticed. What’s a small, kinda boring line on a resume that actually makes you take someone seriously?

reddit.com
u/Dark_Sky_Guy — 18 days ago

I’ve been in sales for a while now (mostly SaaS), and I just went through another round of job hunting. Reading my old resume back and it honestly sounded like I was trying to impress someone instead of show how I actually sell lol.

It was all big wins, big numbers, “top performer,” all that. Looked nice, but it didn’t really say what I do day to day. And I think that’s why it wasn’t landing.

The stuff that finally started getting traction was way less flashy.

Instead of saying I “qualified leads,” I spelled out how I actually filtered them and how fast I got rid of bad ones. Like rejecting weak inbound within a day and protecting my calendar so I wasn’t wasting time on junk meetings.

Same with follow-ups. I used to just say I was persistent. Now I actually wrote out the sequence I use after a demo. What I send, when I send it, how I push for a decision. It feels almost too basic when you write it, but it reads way more real.

Speed was another one I didn’t think mattered until I wrote it down. I tracked how fast I respond to inbound and how that affected show rates. Again, nothing fancy, just numbers tied to behavior.

Even handling objections, I stopped writing “sold value” and just explained how I connect pricing back to something concrete for the buyer. Way less buzzwordy.

Also added a line about some simple docs I made for myself (discovery checklist, objection notes). Nothing groundbreaking, but it shows I’m not just winging it every call.

When I rewrote everything, I ran it through resumeworded just to sanity check it. Whole thing ended up feeling almost too plain compared to my old version, but that’s the one that started getting replies.

Curious what other people here have noticed. What’s a small, kinda boring line on a resume that actually makes you take someone seriously?

reddit.com
u/Dark_Sky_Guy — 18 days ago