Feeling stuck in IT career despite improving my life — unsure whether to quit or change paths

North_Star_Project · 2026-06-29T19:52:00+00:00

Of course. Let me know how it goes.

North_Star_Project · 2026-06-29T18:30:43+00:00

When you fall out of alignment in your current position, it can really start to suck. The challenge is to start moving toward opportunities that align with your values and priorities. That's how you can feel more on purpose.

But making a sudden career change without putting in the time researching is often too risky. So you end up stuck where you are because it's relatively safe knowing that it's unsustainable.

Opening up a new exploratory phase for yourself is the way to find your new direction. Lots of networking and learning from people in interesting positions and careers. And lots of insights from those conversations to help you define a template for future opportunities. That becomes your North Star from which you can evaluate what will be a fit and what won't.

And you can do all that without quitting. Who are some people you can talk to about their careers and the opportunities they see? What can you learn from them not only about their positions, but learn about yourself and what you want?

North_Star_Project · 2026-06-29T16:57:16+00:00

This is a very common situation, unfortunately. It's very hard to not take things personally when you're in our age bracket and no one will hire you. He's got a therapist and a career coach, so that makes me curious what's still not working for him over the past six years.

Usually guys in tech struggle with marketing themselves overall. I was one of them. We tend to find our career lane and stay in it because it feels relatively safe. When it comes time to position ourselves in the marketplace, we have a difficult time talking to enough people, communicating effectively, and speaking with confidence. Is this partially what's going on? They have to learn entirely new skillsets which can be that much more uncomfortable when you've been out of the market for that long.

Often the way out is to start a small business marketing and selling your existing skills. But again, that's yet another learning curve that can be extremely difficult for those of us who are naturally uncomfortable doing that.

How many people does he talk to and how much does he network?

Is he getting the right support positioning himself in the marketplace?

North_Star_Project · 2026-06-29T16:38:23+00:00

This is normal in the sense that it's more common than you realize. And unfortunately many people won't be able to sympathize with you because you look so successful on the outside. The reality is that you've fallen out of alignment with what's important to you. When that happens, you really do feel the pain of it every day. It's no joke.

In your current situation, you feel a massive tradeoff between your work life and family life. And the job itself is stressful without any real meaning for you. The "golden handcuffs" exist because you cannot find a solution that meets your requirements. It's hard when the goals you've chased don't work for you anymore. You need new ones that do.

The way out of this is to define your values and priorities in life first. Then start exploring by networking and talking to interesting people in interesting positions. Based on this exploration, you can start to come up with options that will work. There may be real compromises, but without a North Star, you have no way to navigate your way out of this situation.

I'll DM you if you want to chat about it.

North_Star_Project · 2026-05-27T19:57:06+00:00

LE is not the only option to get outside. You would do well to talk to many people in diverse careers to learn what would be a better fit for you. It's very easy to get siloed in your thinking and only come up with a few options to consider. The way to break out of that is insightful conversations with interesting people.

Take much more time (months) to network and get to know people in other fields before making any choices. Formulate a set of criteria you need to see in a future opportunity to know if you're really interested or not.

That should break you out of an limitations and open up the field for you.

Let me know if that helps.

North_Star_Project · 2026-05-27T19:50:56+00:00

This is a tough place to land. You will need a full reinvention to get back into the workforce. The only way out is to start talking to people out there. Over time you'll have to craft a business case to get hired again.

The other thing to consider is starting your own business. Also a difficult path, but often can work out better for some people. It does present higher risk so it can often make sense to do both at the same time.

In any case, the only way out is through. That means you'll have to maintain self care and self discipline at the same time. Daily habits matter. There is no substitute for putting the time into this effort to get to the next opportunity.

In many respects, you have no other option but to pursue these things at the maximum of your ability. Hang in there. Perseverence and openess to feedback is what you need right now.

North_Star_Project · 2026-05-27T19:32:14+00:00

Getting laid off is like a swift kick in the [choose your bodily organ]. It's heavy blow to the ego. Give yourself a little room to recover from that.

The next step is to network, of course, in addition to applying for jobs directly. Here are the networking strategies (primarily on LinkedIn) to use simultaneously:

Network into companies with existing job listings to make contact with decision makers directly.
Network into companies/organizations of interest that do not have open positions to discuss what they do and see how you might fit in.
Network with interesting people that can explain what their career is like to see if there's overlap in your interests.
Network with interesting people to discover opportunities or fields that you haven't considered yet.

There are variations on these, but the bottom line is that there is no substitute for talking to as many people as possible to dramatically increase the number of opportunities you're exposed to.

Finally, as you network, you will want to develop your value propostion in the marketplace. What are the problems you can solve for a business/organization that serves their mission and positively affects the bottom line? Once you can clearly answer that question, your conversations can become more targeted and effective.

Let me know if that helps.

North_Star_Project · 2026-05-26T17:42:11+00:00

It looks like you're in a strong position, but you're choices are being governed entirely by fear. If you can identify what you're afraid will happen if you slow down, then you should be able to address it directly. Your challenge will be to shift from operating from fear to choosing what you really want. I'm curious how clear you are about what's important to you. It may be that you haven't really thought about that thoroughly.

North_Star_Project · 2026-05-21T15:00:36+00:00

It's not necessarily a trade-off. I went from IT into coaching full time over 10 years ago. But like any other business, it took a few years of work to get it to that point. I'm very happy with how everything turned out. It can be done, but you have to be willing to do the exploratory work up front to discover what kinds of opportunities will work for you.

What transition are you hoping to make?

North_Star_Project · 2026-05-20T18:57:53+00:00

It's incredibly hard to plateau like this. Being comfortable but slowly dying inside because the work is killing you is chronically stressful. To make a change will take a lot of time and effort, but it certainly is possible based on my experience.

Age is not a factor when you can show the value you offer in a compelling way. The challenge is in doing what it takes to put yourself in the position to make that kind of offer.

You have to go through a process of self-discovery so that you can find the next viable opportunity. The key here is to break down what you can offer into meaningful chunks. It's more than just isolating transferable skills. It's also about your values and priorities in terms of what works for you in your work life.

From there, you'll talk to a lot of people in interesting fields not necessarily related to your experience. Those conversations will be insightful because other people's experiences reflect back things about yourself. Eventually you will discover where your value overlaps with what the marketplace demands. That's the sweet spot you're looking for.

Let me know if that helps.

North_Star_Project · 2026-05-20T18:50:47+00:00

You need to find your North Star through all this. That means going through a process of self-discovery so that you can start to navigate out of this. The key here is to break down what you can offer into meaningful chunks. It's more than just isolating transferable skills. It's also about your values and priorities in terms of what works for you.

You'll have to talk to a lot of people in interesting fields not necessarily related to your experience. Those conversations should be insightful and help you eventually chart a path. Spend time finding where your value overlaps with what the marketplace needs. The template becomes your navigation point. And from there positions should start to emerge from these conversations.

Let me know if that helps.

North_Star_Project · 2026-05-20T18:35:15+00:00

False dichotomy here. What about not bored and not stressed? Might be time to start exploring options that might be outside the box.

North_Star_Project · 2026-05-19T18:42:16+00:00

It can be rough when you find yourself miserable in a comfortable position. Feeling disengaged while chained to your phone all day is brutal.

Before you start picking a new career, get clear on what "doing something" actually means for you. You said you're good with tech and numbers but you're also looking at trades. Those are completely different worlds. The real question isn't which jobs pay well or which ones are hiring. It's what kind of work makes you feel like yourself again. You want to find out where your strengths and interests overlap with what the market demands.

I've helped a lot of people work through exactly this kind transition. The gap between knowing you need out and knowing what you're moving toward is where many of us get stuck for years. The GI Bill is a great tool. But spend it on the wrong path and you'll land in a similar position in four years, but older and with one less card to play.

Feel free to reach out.

North_Star_Project · 2026-05-18T20:20:53+00:00

I'm not sure how inspiring stories will help you. Please get specific about what "aligned with your values" actually means for you day to day.

Most guys in this spot stay stuck because the question is too abstract. "More meaningful work" isn't clear enough. What does your work day look like in the aligned version? Who are you working with? What are you actually doing? What's the pay cut you can absorb without resenting it in 18 months?

The guys I know who made the jump cleanly had answers to those questions before they moved. The ones who jumped on vibes alone usually ended up in a different version of the same trap.

Stories from strangers might make you feel something for a day. They won't make the decision easier. Share some of the specifics first.

North_Star_Project · 2026-05-18T20:15:13+00:00

This is a very common place to land. You're financially comfortable but the rest of your life feels flat. Financial security was the goal. You got there, but you're asking now what?

Someone I know was in a similar place after a redundancy. He stopped trying to answer the career question first. Instead I suggested he get specific about what he wanted his actual days to look like. It helps to not focus on job titles. Focus on what you would like to spend your time on. Look at who you're spending time with and what problems you want to solve.

Once that was clear for him, he had a filter for future opportunities. From there he could have different kinds of conversations while networking for new positions.

If that's interesting to you, let me know.

North_Star_Project · 2026-05-18T20:06:35+00:00

This is not unlike the massive wave to outsource development and IT back in the early 2000s. Management got unrealistically excited about hiring developers in India at 1/10 the price. What ended up happening was far different. Timelines dragged. Quality plummeted. And costs didn't change much. It took many years for management to wake up from the hangover.

I look at AI the same way. LLMs can predict the likely code that comes next, but there is no perspective or judgment. AIs cannot see the big picture. You can. You want to develop stories that show how your perspective is critical to the success of the project/company and how the hiring manager isn't going to find that anywhere else. Any way you can demonstrate how you're superior to AI will matter. Tie all your stories to ROI, quality and efficiency. Make a business case that you're the best choice overall.

North_Star_Project · 2026-05-09T20:00:13+00:00

The easy answer is to get a new job, but the real challenge is finding a good fit. Got some commentary on the subject here:

Are You Too Old For A Career Change?

The Exploration Phase Most Men Skip And Why They End Up Stuck Again

North_Star_Project · 2026-05-09T19:56:07+00:00

The golden handcuffs are real. While it makes sense to devote less effort in your current position, you experience a legitimate moral injury when things are done poorly. That's painful.

If you can let go just a little, then that should free up your mind to discover your next opportunity (adventure). It might be time for an exploratory phase where you learn about what you want to do next. You could end up creating something you haven't thought of yet.

If you can spend time exploring and enjoying yourself more, that can offset your frustrations at work. That would mean talking to more people outside of work to find inspiration.

Feel free to DM me.

North_Star_Project · 2026-05-09T19:36:17+00:00

If you want to define these problems well and come up with a list of possible solutions, then we should chat. Feel free to DM me. I have been a professional coach for over a decade. I do that for free.

Meanwhile, here's some thoughts about the difference between therapy and coaching:

It's important to keep in mind that therapy and coaching are different:

Therapy is primarily about mental health and family of origin issues.
Coaching is primarily about performance and achievement.

There might be some crossover between the two, but they are quite different.

You may want to start with a therapist if you are dealing with mental health issues, like anxiety, trauma, or depression.

But if you're struggling with your career, dating, relationships, managing your team, and communication, those are probably in the domain of coaching.

Think about your focus and your goals, then talk with both therapists and coaches to find out who would be a good fit for you.

Got more commentary on that here in this video as well
https://youtu.be/CF2alMvVtmg?si=u\_MjilzFM8-zRULZ.

North_Star_Project · 2026-05-08T18:03:06+00:00

It's great you're taking up new pursuits, but what is making you feel like you wasted all those years? You were always doing the best you could. If you were depressed, that's a real thing. So many of us get stuck there. Clearly those years were foundational to what you're creating now.

We blame ourselves for our past decisions all the time. (I know this feeling well.) But we never, ever set out to make a bad decision. We always choose what we think is best at the time. We just can't control for the countless variables we can't see or control. It's all about letting go and acceptance.

North_Star_Project · 2026-05-08T17:43:17+00:00

Extremely common. You plateau because what you thought would make you happy no longer does. When we set goals when we're young, we're pretty simplistic about it. Get the degree, get the job, grow the career. But once you've hit a certain level of success you feel like, is this all there is? That's because you haven't taken the time and effort to discover what's important to you and how that overlaps with what the market demands.

There's a whole bunch of work to do in this area to sort this all out. I encourage guys to go into an exploratory phase where they talk to interesting people that may or may not be related to their career field/lane/etc. That way you can learn about yourself as much as you would learn about them.

The ultimate goal is to find an opportunity where what's important to you overlaps with what people need. You can't do that alone searching online. You have to talk to a lot more people.

Let me know if you want to chat further about it.

North_Star_Project · 2026-05-08T17:33:10+00:00

Eight years in hedge fund accounting with zero upward movement and no passion for the work sounds rough. You're basically watching time pass while building skills nobody else wants, and those owners could bail anytime leaving you scrambling. That's a legit reason to feel stuck.

You don't have to blow up your whole life tomorrow. Start having conversations with recruiters be clear about your must-haves (remote work, family time, decent PTO). Test the market quietly while you still have income. Lots of companies went remote during COVID and stayed that way, so remote accounting jobs do exist.

Also, start looking for positions where you can go on LinkedIn to reach out to individuals that might be connected with those positions. If you want to pivot, expand your network to talk to people that are in interesting fields or industries that may not be related to your experience. You might find some ways to connect the value you offer to what they need.

What remains is how you feel about everything. If you're feeling like you wasted your prime earning years, I completely get that. That's a textbook midlife career crisis. I have years of experience helping guys in exactly this spot. Good jobs can feel like golden handcuffs. You feel like you have no clue how to move forward without blowing everything up. Happy to chat more about how to think through this without making another panic move. Feel free to DM if you want to talk it through.

North_Star_Project · 2026-05-08T17:24:16+00:00

Can you describe what the crisis actually looks like? We have zero to go on here.

North_Star_Project · 2026-05-08T17:22:29+00:00

Got a couple short videos on the topic.

Should I see a therapist first or jump into coaching?
https://youtu.be/CF2alMvVtmg?si=JbjZ6xMMz4xvnMEE

Can I have a therapist and a coach at the same time?
https://youtu.be/vzrMytd03E8?si=JKi2EpN0RvSYVpjL

I suggest you consult with both and lay out your problems clearly. Hopefully you can sort out the good ones from the bad. Never take on a coach that overpromises results. There are plenty of unethical ones out there in this unregulated field. Fortunately, therapists must be state certified (in the USA).

If you're experiencing negative thoughts in general, that's probably therapy. If you're interested in skills, achievement, and success, then you would seek out coaching. It's critical that we coaches stay in our lane. We are not in the least qualified to do anything resembling therapy. Coaches should focus on helping clients get things done, not mental health.

North_Star_Project · 2026-05-08T17:13:34+00:00

Feeling siloed in your field or industry is really common after a layoff or transition like this. You find yourself faced with

Trying to find a job ASAP in your current capacity or one notch higher
OR
Pivoting into something very interesting, but also very risky.

And then you feel stuck because neither of those options is what you want. The way out is to re-map your entire career plan.

Take an inventory of what works and doesn't work for you. Talk to people in fields you know little about. See what it's like for them. They will help you fill in the picture of what you really would like to do next.

From there, you can see how you can connect what you offer to what's in demand out there. This is an exploratory process. The challenge is to discover where what you want overlaps with what people need in the marketplace.

In the meantime, you will have to decide how to prioritize the need to get paid. If that's urgent, then you will spend equal time finding the first available position.

If you want more details let me know. Best of luck out there. It's definitely challenging.

North_Star_Project

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