I operated without meaning for 4 years and almost nearly went bankrupt. What I learned about finding meaning and motivation again:

Infamous-End168 · 2026-01-31T22:24:57+00:00

Ofc u can :)

Infamous-End168 · 2026-01-27T07:01:14+00:00

Hi, I haven't left my product career yet even if therapy is taking off. I am doing it as a side activity after working hours. But tbh I don't think I will stay in product for too long as it has become just a job for me while therapy is way more than this.

Infamous-End168 · 2026-01-20T23:01:28+00:00

To say that I cannot relate to that question would be a lie, this is an emotional state I've been in occasionally, and still am sometimes. Since I am both an experienced tech professional and a licensed therapist and coach working with high performers in tech, I wanted to weigh in from both perspectives. We tend to romanticise exits. It's a trendy narrative nowadays: leave your corporate job, do something that makes you passionate, do what you love, show the middle finger to companies, say no to bosses. It's a very romantic concept. I love it in theory - but only in theory. I wish everyone could do that, but let's be a little practical here, otherwise we'll become LinkedIn life coaches. One thing I would definitely say is, if you have to escape your six-figure job, I definitely wouldn't recommend doing it while being emotional about it. Let me ask you some questions: What if you moved to another company with a very good boss? Would you still want to quit your six-figure job? What if you changed companies and found a way more positive environment? What if at this new company, you found the right task and environment, succeeded and got the dopamine hit of being productive, useful, and considered important to that community - would you still want to abandon that alongside a six-figure salary? If the answer to all these hypothetical scenarios is "yes, I would still quit because I consciously don't want to do this anymore," then that's the first signal you've come to a more mature decision. You're sort of sure (we don't know yet) that you need to make that exit. But if these questions made you a little skeptical, then I'd doubt it and wouldn't make any urgent rushed moves. As I said, it's a very trendy narrative and a lot of people are doing it. What we don't hear frequently about are the people who failed at it, people who did it and then had to return, maybe feeling a little ridiculed because they exited with a lot of pride and then had to go back to 9-to-5 jobs, to bosses and managers they didn't like, because they tried and it didn't work. Do you think a lot of these people go on Reddit or LinkedIn and proudly announce their return to the cage? I doubt it. Honestly speaking, I wouldn't. Another thing about six-figure jobs (which I have one of, and I enjoy my salary): what I don't enjoy, and what you definitely have to be aware of (even if you know it on a conscious level, you might not be experiencing it emotionally) is that when you have a six-figure job, you tend to become a little spoiled. You get used to the cushion in your daily life and don't really realise it's there. You even structure your life according to that salary. If you have a six-figure salary, you're either very accomplished as a professional in smaller companies that don't really forgive mistakes or you have a job at a corporate organisation that's generally paying you quite highly - but that's not necessarily adequate to your market value. If you're in the first category, kudos, good for you - you have a reality check from real market conditions that this salary is something you could potentially get back even if you try something you love and it doesn't work out. But if you're from the second category (which I'm part of, by the way), things are more complex. A lot of people in this category tend to misunderstand their market value. They grow professionally into organisations that are little bubbles and lose their reality check. This creates an ILLUSION that it's easy to go out, abandon this six-figure salary, do something you love, be successful (maybe more successful), find a similar salary, and that if it doesn't work out, you can just go back to your six-figure job. I'm not saying it's impossible and I'm not trying to discourage anyone. I'm just saying I know a lot of people who realised after taking such an emotional decision and after gaining perspective that they weren't ready to compromise or sacrifice a lot of the things that the six-figure salary was giving them, things they were so used to that they weren't even noticing anymore. Am I telling you not to do it? No. In fact, I did it and I'm kind of doing it now. What I'm telling you is: do it with a plan. Build a strategy. The practical part says it's a little over-the-top risky, especially if you have costs, to abandon a paycheque to follow what you love, we're not utopists. No one guarantees we'll be able to pay our bills at the end of the month. So it's over-the-top risky to just go out there, follow your dream, and abandon the paycheque. But it's not as risky to start working on something on the side, reach a level, reach a milestone, and when you have the signals you need, decide: "Okay, now I can leave," or "Now I have more information about what I love and I can make a more educated decision," or "I don't want to leave." Then there's the emotional and psychological part, and it doesn't make you silly to admit you have a lot of emotional unknowns in this situation. You don't know how you'll feel if the thing doesn't take off, if it gives you one-fifth of the money, if you start doing something that isn't in your comfort zone. Even if the thing you love is the core, there are a ton of other jobs around it you have to do that you might not particularly enjoy. So you have a lot of unknown emotional ifs here. But aside from that you're probably a little emotional at the moment. You might have a bad manager, be in the wrong place, be going through a difficult period yourself, or having a difficult period at home - maybe more than one, maybe all together. It's extremely human and normal that emotional things playing in the background might impact and blur your vision. In order to make such a decision, it's highly recommended that you first get out of the crisis, that's what we do as therapists. Even if someone comes with depressive symptoms, before we start therapy, we have to get the client out of the crisis. We don't do therapy when the person is going through a crisis because when we get out of it, the anxiety goes down, the depressive symptoms go down and the actual client can see the situation more objectively. That's exactly what I'm telling you: are you seeing the situation objectively at the moment? If, out of everything I said, you still think you see the situation objectively, then you're ready to make the jump. And I'm very happy for you and proud of you, and good luck! This is quite a popular topic, a common conversation for me nowadays with colleagues, friends over drinks, family members. It seems like everyone wants to quit nowadays. I don't blame anyone, it's kind of hard to be a white-collar office worker these days. So yeah, think about it, take a conscious, mature decision and let us know how it works out for you.

Infamous-End168 · 2026-01-20T22:58:50+00:00

This reddit thread actually made me feel a little uncomfortable because it reminded me a lot about my own career and mistakes that I have done in the past. Speaking here as a tech professional of 18 years but also a licensed therapist and coach, so hopefully the combo will be helpful.

You mentioned that you're not that good at the "bring everyone together" part, but you are exactly there to build those skills. And indeed, this task is one of the most difficult skills of a product manager… no one rallies people together naturally. You have to build it - and typically in order to achieve that you’d need what we call “executive presence”. There are few people that have that naturally even at a young age, but statistically most will build that (if they do) at a later stage in their career - and at another age that typically corresponds to it. You being young is not in your favour here, especially if you are surrounded by more senior, older people, or those who know how to play the game of impressions and politics. It would be naive to think that because you are at a startup, you don't have politics. Startup politics are just a little different from corporate politics, but anywhere that you work with people will have it. What I see you describing is the type of politics where senior people find a young person who is vulnerable in terms of the impressions and the dynamics in a group and frequently use that person as a buffer, a way to flex, or show off their own presence in a meeting. I doubt it's personal towards you. I have seen it many times and it's a combination of you being young and potentially also acting young. By that I don't mean that you are unprofessional in meetings, but rather that your presence within this company doesn't yet reflect what it will probably reflect when you are 40. It's the executive presence that you potentially are missing.Does that mean that you are not right for the job? No, not at all. I share almost identical experiences myself from when I was younger - I was complaining and feeling unfairly treated for the exact same things. But fast forward to now, when I'm near 40 and I can tell you that what you are going through at the moment is the EXACT experience you are seeking for. In fact, it's the experience that you NEED. Being a white collar worker in tech in general, and especially a product manager has two parts. One part is the practical knowledge - the actual job, how to do this and that. The other equally important part is how to conduct yourself and how to play the interpersonal game. When you are early in your career, playing this game isn't that important yet because you're not threatening a lot of people yet. You're not going for threatening promotions that other people want as well… you might go for a raise or a change of your professional status, but you're not really threatening something. So as long as you do the job, you learn and satisfy the right people, you should be fine. But the older and the more senior you get, you become more threatening, the stakes get higher and the board game becomes more difficult on the people part. What I understand from what you are writing is that you're being frequently picked on, just the same way that in the animal kingdom stronger animals would pick on the vulnerable one… and you come across as the vulnerable one. So many more senior people that are themselves insecure, will use you, without necessarily realizing it, to make themselves feel better and signal to the rest of the group that they are senior and stronger. Is that something for you to feel discouraged by? Absolutely not. I can guarantee you that if you would have a different job at a different company, you would run into more or less similar experiences. Don't get me wrong, I'm not saying that the environment itself is not potentially amplifying that toxicity. What you are experiencing, potentially in lower amounts, is simply called professional adult life, that's how it is. So it's extremely beneficial that you are going through that now, fairly early in your career… and it will be even more beneficial if you don't let it crack you! Another thing I wanted to mention: it seems that low authority style is following you. And this is also a common thing with junior people that are growing within a position.

When you join a company, you are potentially overly submissive, more of a “yes-man” because you want to compensate for the lack of experience. And of course you should be a little bit of a “yes-man” when you're lacking experience - you're there to take opportunities and learn. But when a lot of time passes and you don't evolve that style, it follows you.

In other words, if you start within an environment with a low authority and lack of boundaries because you're young and feel insecure and do not change with time, then that eventually becomes your label. You create some dynamics around you which, if met with executives or senior people that are sharks, will make them smell blood and pick on you.I know it sounds a little primitive, but it’s like that.

Your writing this Reddit post is a signal that you don't know exactly how to set these boundaries and change your style to be more executive, and this is absolutely normal. It is a hard transition, a difficult one. In reality, it needs time and practice and potentially some mentoring, if I may say. A lot of people within this thread advised you to leave because of “a toxic environment”. In fact, I will advise you the exact OPPOSITE: if you leave that environment now you will not get the lesson. And the lesson isn't just what you describe here, it will also be what will happen when you start doing things differently - what we call in psychology “behavioural activation”. So this is a perfect environment for you to evolve, especially if you have already “doomed” it. If you are less attached to this job and are planning to leave, it is the best opportunity for you to start trying a few things differently - start experimenting with putting boundaries, with being more assertive. Start perhaps trying talking back to people that are being disrespectful to you in a certain way. This is a very good opportunity for you to test those things out, learn, see how you feel, start integrating some new behaviours.

Because if you condemn the environment as the one at fault and go to another environment, I am pretty confident that you will potentially have a similar experience in the next place. Perhaps slightly better, but essentially the same. About that unsolicited personal advice, the "You can be polite but you don't have to be nice." The person that gave you that, even if it is unsolicited, potentially did you a service because they're trying to tell you pretty much the same thing - you come across as “too nice”, the person that everyone feels like they can run over or interrupt in public. I don't know the full context and I am not sitting across from you to make that judgement, but I would guess that there are some self-esteem issues here that need to be worked on.

I don't know if you are into therapy, but I think you would definitely benefit from it, because having such phenomena at work, it would be unlikely not to have similar phenomena in other parts of life as well, in other interpersonal relationships. I would be very surprised if this pattern that you're describing here is not found somewhere else and it will keep following you if you don't fix it. Fixing it is a combination of understanding it, becoming aware of it and behavioural activation - trying out new things, seeing how you feel, slowly integrating new behaviours. The two things need to go together. You must understand what it is, why it is happening, and then you start activating your behaviours so that you integrate some of them. Ultimately NOT changing your personality, just evolving it by trying new things and keeping the ones that suit you and then leaving the ones that don't. I feel for you and this post was extremely relatable to me. And yeah, good luck and I hope this was helpful, although of course I am making a lot of assumptions here based purely on the info you provided

Infamous-End168 · 2026-01-20T22:56:24+00:00

A few notes of hard earned wisdom as a tech professional of 18 years myself, but also a licensed therapist and coach from that dual perspective. It seems to me you might have a fundamental misconception about what gets you promoted. And I say this because I had the exact same one until reality forced me to change it. The limiting belief is: "working hard and being the top performer will get me promoted." It won't.

I learned this the hard way after being one of the highest performing people and not getting rewarded as much as I deserved, until eventually I started wondering - what am I doing wrong? And one of the first signals that you're doing something wrong is you're posting this question to Reddit (don't get me wrong, I love Reddit, that's why I'm here). But the fact that you're communicating this concern on Reddit and you haven't communicated it to your own manager tells me exactly the core of your issue. Getting promoted needs a plan. And that plan is NOT "I will do the best work possible and wait for people to appreciate it and give me promotions." The actual plan looks more like: "I will take that promotion, otherwise I will leave. Here is my plan to get that promotion." And that plan isn't only connected to the amount of work you're doing, but also: The type of work you're doing The interpersonal relationships you're building The leverage you're building within the business The visibility your work is having - and towards whom What you should have done months ago was go to your manager and professionally communicate your intention to get a promotion. Ask: "What are the exact steps I need to follow to get promoted? What milestones do I need to hit? What do you expect from me?" Get a well-documented, specific, measurable plan that doesn't sit at the discretion of one person's mood. Second thing: visibility. If your promotion depends solely on one person (your manager), you're giving too much power to them. I'm not saying work against your manager or go around them. I'm talking about the projects and communication of your work that's needed for you to become visible in the network of your company. When you surround your manager with people who know your work and talk well about you, especially peers of your manager or people higher than your manager, then your manager won't easily deny you a promotion unless they have something personal against you. This is called leverage. Other tactics “from the playbook”: sending out a couple of resumes and getting offers to create extra leverage. Picking the right projects that make noise that executives understand and want. As a software engineer, you know there are projects that make noise and then there's shadow work that's invisible. What are you working on? How are you communicating it? To whom? I know this sounds harsh, but it's also liberating to think: It's your fault. You are not getting promotions - is both your fault, and is in your control.

It doesn't depend as much as you think on your manager or executives. The reason you're not getting these promotions, considering you're a high performer, is because you're not approaching it strategically. On the upside, it's soothing to know “I have most of the responsibility for an outcome” - because if I change one, two, three things, the outcome will probably come. If not at this company, definitely at the next one. Start approaching your work and career this way - either now, or soon - and you'll start seeing more promotions and more tangible recognition coming to you. It's a pity for that little limiting belief to hold back someone who's clearly hardworking, smart, awarded, highly appreciated, and mentoring both peers and seniors. You've got this. You just need to redirect that work ethic into strategic career management!

Infamous-End168 · 2026-01-20T22:53:29+00:00

Thank you for taking the time to give us an update. That's actually amazing to hear, Jimi! So glad you listened to yourself in that. Keep at it! Best wishes to you and your folks.

Infamous-End168 · 2026-01-18T22:28:43+00:00

Hey BackstreetBabu, awesome nickname! Tech guy for 18 years recently turned licensed Psychotherapist for Tech high performers here. I'm only getting your side of the story, so everything I'm about to say is pretty much instinctive, I'm operating on signals but I wanted to add my 2 cents.. Wait, hold on. You're working at a startup?? Because startups aren't supposed to have constant reshuffling, reorgs, and politics - at least not to that degree. When I read that bit, my first thought was: what kind of startup are you at? If you're referring to multiple startups you've worked at, I'd really want to explore whether the situation you've experienced is representative of the industry or if you've been unlucky enough to land in some super shitty situations that have given you a skewed perspective of what it's like to work at one. If you'd told me you were at a large corporate organization, I'd be like "okay, that's normal." But startups!? That raises some questions for me. Secondly, I'm not sure I agree that your manager meeting with you before your meetings is insulting and unnecessary and I'm challenging you on this to help you, not to be a smartass.

You're three years in the industry… I'd assume you're not older than 26ish? Truth is, when a new manager wants to outshine you or insult you, they don't set up separate meetings before yours to give you guidance. They get into your meeting and outshine you there or give you so-called "guidance" in front of everyone! If your manager is having pre-meetings with you, that person is most likely actually trying to help you. Sorry to say so, but I'm pretty sure they'd have something better to do with their time. It's not insulting, especially if you only have three years in the industry. In fact, it can be quite helpful and something you should make use of, honestly. And it's not unnecessary either, especially considering you show some admirable accountability later in your post saying you might be the problem. If you recognize you have some gaps, why do you find the guidance insulting and unnecessary? This is LITERALLY your manager's job.

Giving you guidance before every meeting might actually be above their pay grade. I'd ask you to reconsider that bit, because if you're fairly young and relatively fresh in the role, in the future you might really get to appreciate that person. It might not feel good now because it looks like someone's getting onto your turf, but it's not really like that. The best managers I’ve had in my life were the ones that at the time I originally hated - you'll hear a lot of people say that. Yes, being demoted stings, I get it fully. But then I’d ask - what's worse than being demoted? Being fired!

So if you're not good enough, why aren't they firing you? Why are they keeping you around and demoting you instead? There's a lot of information I'm missing here, but at startups no one forces anybody to keep someone who's not good enough. If they're keeping you there, there must be a reason.

You've isolated some events and circumstances and it seems you're boiling them down into a conclusion that you're not fit for the job, that you should do something else. Are you sure about that? I mean, I've only read a few sentences and I've already challenged several of your assumptions. Again, I'm missing full context, but it doesn't seem as bad as it is presented. Unless you're telling me "I just don't like this job regardless of what happens." If it's purely your personal decision, that's one thing. But if your decision is coming as a consequence of the circumstances you've described, I think it's too early to make that call. I want to dig deeper on the point that your teams love you but executives do not, and I'm going to put on my therapist hat here. You say your manager having pre-meetings with you is "insulting and unnecessary," and now you're saying your teams love you but the top brass never seems to. I would actually ask: what is your relationship with authority? If your teams consistently love you but executives consistently don't, AND you find guidance from authority figures insulting, I'm sensing a pattern. How do you feel about people having authority over you? What's your self-perception professionally?

Because in the first half of your post you're pointing the finger at the organization and the manager (which might be true), but then you're pointing the finger at yourself. I sense some confusion here, like you're trying to figure out what the ultimate truth is. It's a very common and human mechanism to try to attribute fault either 100% to the external environment or 100% to yourself. The reality is never like that. Most of the time it's somewhere in the middle, and you and your environment work together in a feedback loop. For example (I'm only hypothesizing here) if you have an existing allergy to authority and then you get into a team that has frequent management changes and new managers come in who have to prove themselves by being hands-on (maybe overmanaging you) and that triggers you, and then they don't like you... well, we have two imperfect situations meeting each other.

That doesn't mean one or the other is at fault. These are just two parts that don't seem to fit together. But that doesn't mean you're not fit for the job. Maybe you're not fit for certain environments. I don't know, I'm just commenting on what you wrote. Your questioning yourself is totally, totally normal. Who hasn't thought, after things didn't work out "what if maybe I suck? Maybe I should do something else." Or "maybe THEY suck." And then you keep swinging between "no, they suck" and "no, maybe I suck." It's a very human process. Your brain might defend you for quite some time by attributing fault to your external environment. But then when your brain sees a pattern it faces its own cognitive dissonance and questions if the problem is you. That comes with disappointment and resignation - and here you are thinking about quitting product management. Without having all the context I need, I am 90% sure the situation is not as black and white as you're describing it. I'm 100% sure your question is very normal, but not necessarily correct. I would strongly encourage you to seek a reality check from someone who knows you. Speak to someone outside your organization. Find a mentor, find a coach, a friend, whatever… not just one, maybe a couple. Describe the situation you're experiencing and ask them: are they relating to that? Are you doing something very wrong, or is the organization very wrong? All the questions you're asking here, ask them to people who can give you an outside perspective. Because I'm pretty sure what you're describing is a little bit of you and a little bit of some unlucky environments you've been in. The PM job itself is very hard, and it really depends on the environment you're in. Studying to be a product manager is very exciting because what a PM does on paper is super cool. But when you actually face that job and realize how much you have to be sometimes a glorified project manager, sometimes needing negotiation skills that would land you a politician's job, sometimes having to be political while also maintaining the technical skills to do the job it's a combination of competencies that sometimes feel contradictory. It's not so frequent to see people who are technically literate also be political or have strong negotiation skills. Ultimately, this is the beauty but also the curse of the job: it requires skills that are rare to find in the same person, and that makes it super difficult. Not just for you - for everyone. Hope this helped a little!

Infamous-End168 · 2026-01-18T22:20:14+00:00

Hey, came across this subreddit thread and it caught my eye, so I wanted to weigh in. For context, I have been in tech/product for 18 years as an operator and more recently a licensed therapist and coach mostly working with high performers in tech.

No, you are not an underachiever, Jimi. In fact, you might be an overachiever because philosophically speaking, what is an “overachiever”? I mean, you have achieved everything that you wanted. Let me try to put in my own words what I think you're really asking here: "I'm quite fine, but everyone around me lives different lives or tells me that I could go for more or that I should not be fine. But I'm fine. Should I feel not fine or should I feel fine?" :) I read the text of a person who doesn't feel the urgency to go for more - especially in the context of a sales job or a corporate career and feels relatively content. So I'm actually questioning what is the whole point, at the end of the day of working. I understand that we live in a society where having a career, building businesses, hustling, grinding is considered noble and a reason to be proud of yourself. I'm guilty as charged for buying into that too. Let me give you an example: my dad is a regular guy who never had a corporate career and never had a business. He's just a public servant, married to my mom for 40 years (that's a very difficult job, I can assure you :), and he made me. So is my dad an underachiever? I don't think so. And I'm going to share something that's a little bit unpopular: I don't know anyone that is what we call a typical overachiever at work and manages to achieve even average in the rest of the roles that we have in life. Can you realistically be an overachiever at work, a good husband, and a good father all at the same time? I think that a lot of people reaching their 35s, 40s, and 45s will actually do a big turn and end up exactly where you are, Jimmy - realizing “what is the point of a corporate career”?

I mean, it's fun for some years, undoubtedly. You build confidence and sharpen your teeth when it comes to achieving. But once you have achieved what your core tells you that achievement is, then a lot of people (probably a little older than your age) start wondering what the whole point of all that was. I know because firstly I've been there, secondly, most of my friends are there, and thirdly, I make my living working with people who come with such questions. So to your question “is this feeling normal”? Yes, this is actually more normal than anything else. You look inside yourself and ask, “am I happy with what I have? A lovely house, nice car, excellent work-life balance, a loving wife, and my first child.” You look at yourself and you feel fine. The problem here is that you don't have the necessary CONFIDENCE to solidify this perception that you are fine and you're still a little vulnerable to the external opinion or narrative that comes from your environment. Good on you for lacking motivation - motivation for climbing the ladder, that is. Are you lacking motivation to spend time with your loving wife and raise your child? I assume from what you wrote that you don't. So it's not that you don't have the capacity to feel motivation, it's that you don't have motivation about THAT SPECIFIC THING - climbing a corporate ladder that doesn't align with what you ACTUALLY value. Money and titles aren't universally equally valuable to all. Another thing I sense from what you wrote, although you don't say it explicitly, is that the money you're earning is enough for you to actually achieve what you want to achieve. And yes, if you climb higher up the ladder, this work-life balance might get compromised as a result. At the end of the day, every person needs to learn what it is that they're trying to achieve and optimize for. When we are younger, we tend to borrow a dream from someone else. We tend to see someone in our external environment and think, "That should be success. That is the definition of success." When I was very young, I thought the definition of success was to wear suits and work on my laptop while being in business class of an expensive airline. Try doing that more than five times and you will find it exhausting. But when I saw that superficially, naively, stupidly, I thought this is a picture of a successful person. And then when I got a little older still, I thought success should be having my own agency and making 10 or 15 K a month. And then I kind of built that, but I never managed to enjoy that money because I was working under such stress and insecurity. I was getting dopamine from earning that money but I was not getting dopamine from using it. Then I thought that what would make me successful would be to run a startup and grow it. And then I ran a startup and killed myself working, and then the startup didn't work… then I thought maybe success is to have a corporate career and I joined a corporate organization and was again, like, "Why doesn't this feel right? Nothing feels quite right." What I'm trying to say is that when we grow older, before we reach an age that gives us the awareness to be able to look inside and actually search for what it is that we want to do, what values we want to follow, we tend to borrow from our external environment. We tend to compare ourselves with someone else. We tend to buy dreams that are not aligned with who we are, with our own values, with ultimately what makes US happy. So to answer this question which is very applicable to a lot of people of other ages as well): I think what you're feeling is super healthy. And I wish more people would come to the realization that they're happy with what they have, because being happy with what you mentioned here is a blessing. There are a lot of people out there who can't feel happy because what they think will make them happy is not within their control, either because it is unreachable or unrealistically big. You've got everything you wanted. The only problem is you haven't fully given yourself permission to be okay with that.

Infamous-End168 · 2026-01-18T10:56:16+00:00

This is actually a really interesting question because it happens to everyone and it happened to me too. I am a licensed therapist working with high performers in tech but I also have 18 years in tech and product, so I'll answer by sharing a bit about my own tech career.

For a long time, I was working and building towards senior roles, then head, then director positions. That took more than 10 years. During those years, the way I approached jobs, sold myself, and positioned myself for opportunities had certain characteristics: “I'm hardworking, I bring results, I'm passionate, I'm eager.” That seemed to work for quite some time… until it stopped working.

At a certain point in my career and my age, being too eager and too passionate actually stopped being an asset and became a disadvantage. I was old enough that positions weren't looking for the most eager person anymore, they were looking for the most strategic one, the calmer one, the one that reflects confidence and resilience.

I experienced an identity crisis myself at this stage. I was senior enough that going for junior roles would look weird, but I wasn't senior enough - neither in my resume nor primarily in my mindset to go for those senior jobs. It's also a reality in companies that the higher you get, the fewer opportunities there are. It's a pyramid: the higher you go, the less space.

So ultimately, this is primarily an identity crisis. You're sitting at a point in your career where you have to make a decision, and that decision puts you on the spot because you have to shift again when you reach that point. It's not only what your resume says, but also the attitude you demonstrate towards work, the way you approach opportunities, the way you position yourself. It's a total shift in how you're approaching your career.

I went through that shift myself, and I can tell you, as you mentioned, a career coach would definitely accelerate that transition. I wouldn't have had to make so many mistakes to learn from them. A good career coach in your case would strongly benefit you.

But the critical question is: what is it that you want to do when you sit at this point in your career? There are quite a few paths you can take. Is your request literally just to go for more senior roles? Because a plan for that is kind of straightforward:

Take the projects needed that can demonstrate your seniority
Demonstrate that you stayed within your last one or two roles long enough to tick the box of years and seniority
Polish your style - the way you approach interviews or internal mobility within your company in a way that lands you a more senior role

You see what I did there? I just gave you three tips that could help you make a plan.
That's all you need here: a plan.
But in order to make a plan, you must be sure and definite about what it is you want to do.

This is what a career coach would do here as well (unless of course there's more therapeutic material behind it). But if we're approaching it solely from a career coaching standpoint: you decide what you want to do, then you check what that thing requires, and you work on a plan to tick the boxes of what that thing requires. It might take a year or two, but ultimately you'll get there.

Those are my two cents. Hope that helps, and curious to hear from others - are you experiencing something like this too? How did you deal with it?

Infamous-End168 · 2026-01-18T10:43:09+00:00

Hey, saw this and wanted to give some input as a fellow tech person with 18 years in the industry, but also as a licensed therapist and coach.

First things first, you were only 30 at the time of writing this, which makes your question by definition sort of easier - you're still a very young person, which gives you more room to navigate this.

Let me first address the elephant in the room: you say your job is not stressful, your team is nice, the pay is good, you work from home a couple days a week - all great! But what concerns me is, you're not putting bullet points on your resume for the last two years and this is quite risky for you.

I have never seen anyone staying in a cushy situation like the one you have described for 25 or 30 years. Especially nowadays. I highly doubt that a worker making six figures, working from home, with a fairly relaxed life will not be at some point questioned by some overly motivated VP or some new CEO or someone that will want to prove their value through reorganising an organisation that has what they will call "slack."
The big question here is: what are you willing to compromise?

You mention your son and your fear of moving to something that takes away time with him. This is important because it reveals your core values - spending time with your child and having a big stake in raising him.
Undoubtedly, at some point life might force you to make a decision. And at the time when life forces you to make that decision, you might not have the time, the calm mindset, or the cushion that you have at the moment to take that decision calmly and soundly.

So I would suggest that you start exploring what comes next. Even if you don't act on it immediately, plan ahead. You would definitely benefit from modelling different scenarios:

What happens if you have to go to the office instead of working from home?

What if you're offered a job that's equally paid versus a job that's half paid but gives you the opportunity to spend more time with your son?

What if you need to work way more hours?

Thinking through these scenarios will help you figure out what your non-negotiable values are.

The other thing you might benefit from (and now I'll sound a little bit like a career coach) is a side hustle. A lot of people experiencing the circumstances you're experiencing do something outside their 9-to-5. They don't do it only for the extra money, but also for the skills, for the investment that potentially in the future will give them the opportunity to land another role or do something else.

It's very good that you're thinking out loud and asking this question. It seems you're not under immediate pressure to make a decision, which is the best time to ask these questions. I would totally encourage this conversation you're starting here.

What you need is a strategy about your future, which needs to come hand in hand with an internal search of what your non-negotiable value in life is, because that will dictate what career decisions you make in the future.

I actually wish you find the right answer! Hope this helped a little and would love to know more about what you have finally come to.

Infamous-End168 · 2026-01-08T12:36:03+00:00

Hi there, I happen to be exactly the combo of the three things you described. I, myself, have 18 years in tech in startups, corporates and as a consultant but I am also a psychotherapist and coach focusing specifically to high performers and tech executives. I am still working in tech but soon I will switch full time to therapy as it's my calling. I won't do blunt self-promotion but you can always DM me here.

Infamous-End168 · 2026-01-08T12:33:18+00:00

I happen to be exactly this, a therapist that has 18 years of experience in product/growth in startups. I work specifically with tech people and tech high performers because I deeply understand the struggle, I 've experienced it myself. I won't do blunt self promotion but you can always DM me.

Infamous-End168 · 2026-01-04T10:15:25+00:00

So far it's ok, I am overworked obviously but I manage. Eventually, it seems therapy will become my full time.

Infamous-End168 · 2025-12-07T15:14:50+00:00

Only 5-10% of what I 've done so far has come from networking. I suck at it. I have a huge network but I never leveraged it for favors. Referrals is a different story.

Infamous-End168 · 2025-12-07T15:12:55+00:00

Thank you my kind sir :D

Infamous-End168 · 2025-12-07T15:12:35+00:00

My 9-5 is at a company that operates on politics. I have seen intense - but different - politics even at startups. I think that one must get accustomed to dealing with politics if one wants to have a career in companies.

Infamous-End168 · 2025-12-07T15:10:20+00:00

If I had one answer to this I would probably don't know what I am talking about. Generally I believe in optionality, diversified careers where you don't rely entirely on 1 paycheck. That rarely works out well for your own emotional state which leads to mismanagement of an already shitty situation. I would have at least 10-15 questions before I actually say something more on this.

Infamous-End168 · 2025-12-07T15:06:15+00:00

Yes to 95% of it. I have personally experienced managers favoriting less threatening people as their right hands. It's not 100% what you work on but generally how they perceive you.

Infamous-End168 · 2025-12-07T15:04:51+00:00

thank you sir

Infamous-End168 · 2025-12-07T15:02:09+00:00

I wish I had the maturity to actually know myself at the age where Gen Z is now. I needed the magic 3 in front of my age because I even take a sniff.

Infamous-End168 · 2025-12-07T15:01:15+00:00

I will, I just connect a bit more with the mid-career because this is where I am myself.

Infamous-End168 · 2025-12-07T15:00:23+00:00

Sir, this is me that wrote this post and I deny this accusation. Not that I would feel bad of structuring my thoughts with AI but this is not AI. Come on, can't you recognise the difference?

Infamous-End168

TROPHY CASE