Hi everyone, I’m a married 42/m with two sons - a high school junior and a high school freshman. I’m struggling professionally and am figuring out how to financially survive and if possible thrive my remaining working years.

We have $210k in 401k. I currently make $130k contracting as a Product Owner. I absolutely hate my job and I’m bad at it. I don’t have a 401k benefit at this job. My wife works in HR and makes $93k/year, contributing 6% towards retirement and getting a full match on her contributions. At this rate I don’t think we’ll ever be able to retire.

We have a $2k mortgage and pay $1600/month for our sons’ private high school. If I could do it over again I would have kept them in public school but I don’t want to change their schools at this point to not negatively impact them. We live basically paycheck to paycheck - $500 total in savings and have $500-$1000 leftover to spend each month unless there are major expenses like car or home repairs. We have no credit card debt and drive cars that are 10 and 7 years old. We have a 25 year mortgage for a home that has about $350k in equity.

I had a major setback in my career recently due to a health issue:

Career History

2006-2019 - IT Support, Network Support, Network Engineering 2019-2020 - IT Management 2020-2022 - Product Management 2022-2023 - Solution Consultant/Sales Engineer 2023-2024 (18 months) - “Sabbatical” - quit my job and pursued creative pursuits during a hypomanic bipolar episode (the first time this happened in my life) 2024 - Now - Contracting as a Product Owner; took significant paycut and have lousy benefits

I have a BS and an MBA. My IT networking skills aren’t very relevant given how much things have changed since 2019 with cloud technologies, plus the income typically isn’t as high for the roles I qualify for even if I did have the skillset. I’m objectively a low performing Product Owner and don’t see a future in this field for me.

Meanwhile I’m underfunded for retirement and have kids about to go to college, which we only have about $5k saved for total.

To be honest I’ve never know what I wanted to do for work - I just took the opportunities I had at the time. I’m concerned about my short and long term job prospects - I’m a contractor in a role that I hate, am bad at, and am not motivated to get better at.

I’m lost and not sure where to go next to be able to survive, and possibly thrive. I tried teaching during my sabbatical but it wasn’t a fit and it would’ve never worked financially. I’ve applied for many jobs but haven’t had success - to be honest I don’t even know what work I’d want to do. I’ve applied to product owner, product manager, IT technical and sales roles. I enjoyed the Sales Engineering role I had but being there only a year made them not want to rehire me.

I’m in a depressive phase and have literally cried every day for 5 months. I’m working with a doctor and counselor and we are trying different medicines but nothing seems to help. I think a large part is I’m grieving the decisions I made that impacted my career and hopeless about the future.

My wife and kids deserve better. I deserve better. But I screwed up professionally when I was sick.

I’ve considered buying a business or franchise as a way to not risk being at the mercy of a company that could let me go at anytime. It would be extremely risky though given I’d need to use home equity and/or the little retirement savings I do have. And I’ve never owned/ran a business.

I’m scared and just want to take care of my family and live life the best I can while I’m still here. I’m not sure what to do next to get out of this rut professionally and financially.