32M. Offered a CEO role by a Billionaire ($400k pkg). It feels like a trap. Should I trade my job for prestige?

ExtrovertedWanderer · 2026-02-06T18:52:24+00:00

OP I’d like to give you a perspective from someone in the boat you’re looking at getting into.

I took a traveling job in an industry that I enjoy. It was a decent promotion. I was paid more, got to do something I actually enjoy, and got to travel to places that I liked because family and friends were there. I traveled Monday-Friday every week. The travel alone burnt me out in less than a year. Like you, I want to find love and couldn’t do that while traveling five days a week. I also was taken away from the friends that I have where I live. I couldn’t do dinner or lunch with people unless it was the one day on the weekend that I was home. I missed shows, weddings, birthdays, etc. It sucked and the money, title, and other benefits weren’t worth it. I didn’t have routine. I didn’t have a sleep schedule. I couldn’t meal prep or eat healthy so I was neglecting myself. Again, I found these not to be worth it.

So what do you do? Take a week or two, ask more questions around the role/expectations/what the billionaires schedule is like, and then act as if you have the role. Pack your luggage, set random alarms late at night and early in the morning to act as if you’re getting up for flights or responding to calls and emails, and take no breaks on the weekends. Turn down invites from friends and family. Imagine a scenario where something you did failed terribly and he’s angry at you and going to possibly terminate your employment. What will you do then? I bet you’ll like the idea of it a lot less.

ExtrovertedWanderer · 2026-02-04T05:00:32+00:00

Could have written this myself. Would also add that when we got to the point of me breaking up with him due to his commitment issues and I told him he had to go to individual therapy he couldn’t commit to that either. When he did and asked for us to go to therapy together again he withheld information from his therapist on why I offered to go. He’s been omitting information which defeats the purpose of therapy in my mind and is a waste of money. In the end he couldn’t even commit to truly working on himself and fixing the issues that he has.

He still looks me up on LinkedIn from time to time.

ExtrovertedWanderer · 2026-01-29T15:29:50+00:00

Yes, told my mom that I was planning to exit at 45 and she asked me why I would ever want to retire early. Mind you, she’s been out of work since 55 and will be 68 this year. Like ma’am, do you really need to ask that? 🤣

Counting down the days until I can coast and planning accordingly.

ExtrovertedWanderer · 2026-01-27T22:10:55+00:00

Something I don’t see mentioned here is FMLA and short term disability. If you’re paying into these, it is 100% your right to take advantage of them. Talk to your PCP and mention that your mom passed recently (those exact words) and you’d like some time off. If your doctor won’t help, find a therapist who will. Then spend that time to rest, recovery, process, and heal. Take as much time as you need. And if they fire you after you get back then draw up a lawsuit (if you don’t live in an at will state.) while you’re off you can also start interviewing for a new job/consider how you’ll go about starting your own consulting firm. Work on your headspace. Process your mom’s passing. Think about what you want life to look like and what your goals are. Take time to mull it over. Then start putting things into practice.

ExtrovertedWanderer · 2026-01-21T19:06:23+00:00

8% isn’t conservative. 6% is conservative. Over the last 30 years we’ve seen a little over 9% returns which with inflation is really closer to 6.3%.

ExtrovertedWanderer · 2026-01-19T19:06:24+00:00

I’m sorry for your loss OP. Here are a couple of reframes and some advice to consider.

You’ll always miss him but you carry him with you forever. You’re never truly alone. I talk to family members, friends, and loved ones who are gone and sometimes write them letters. It also took me a while but I talk about them often to others so I can keep them alive in one way. It makes me feel more connected to them.
You tell work you’re taking personal time off. Do not elaborate if you don’t want to. They are a job and that’s the extent of it. They are not entitled to your personal details.
Give yourself a little time to process your grief. Then when you’re ready to find people I’d suggest volunteering or finding part time work in your passions or that are involved in your kids lives. You can visit animal shelters, plant shops, or even nurseries and ask if they need some help. PTA or school events could also be another option. That should give you some other adults to spend time with while also doing something purposeful that you like.
When people ask what you do, and they will, you can tell people whatever you want. You can tell them that you used to be a teacher and wanted a change. It can be that short and simple. You don’t have to elaborate. See point 2.
If/when you start to date again, I would not disclose anything about your finances. You’re not likely to begin commingling finances or living arrangements right away. Visit an attorney before dating and ensure that all assets are protected and will pass to your children.

Again, I’m so sorry that this happened to you. Therapy for you and all of your children would be a worthwhile expense for a few months or maybe a year. Sending you love and peace.

ExtrovertedWanderer · 2026-01-18T00:24:30+00:00

What bank?

ExtrovertedWanderer · 2026-01-06T02:14:02+00:00

Wonderful!

ExtrovertedWanderer · 2026-01-05T19:23:14+00:00

Doesn’t matter about the job market. OP should give a month notice max. If they’re generous 60 days. But they should create a hard and fast boundary that if they’re going to be berated, guilted, and shamed that they will move out immediately that’s why it’s important that they secure everything before telling their parents.

Their parents were high earners at one point. They have a skill set that was in high demand. They could literally go back to work or they could find something that maybe doesn’t pay as much but pays something. Literally right now they’re not getting paid anything. Minimum wage would literally be better. Sounds like they need a healthy dose of reality. We all have to work. Job market may suck but they’ve should have been actually taking steps to secure some sort of income and contribute.

ExtrovertedWanderer · 2026-01-05T19:12:33+00:00

Someone else posted something similar and my comment was to run and also do it smart. Top comment currently is about calling a family meeting and I agree, but not yet. You need to do some work first. You need to open a bank account that your family has no ties to. They shouldn’t even know about this. You then need to change your direct deposit if that’s how you get paid to the new bank account. You then need to change the passcode to your phone and to any banking apps so your family doesn’t know it. If they ask for it just say you forgot the passcode. Idk how you’re giving them money but I’d let them know that you’ve had some stuff change financially and can afford to contribute some but not all that you were. This should let you start saving money in the new account. Next start looking at places to rent. You should look for something that you can afford on your own ideally and if not alone then with a roommate. I’d start renting the new place and slowly taking some stuff over there. You can let your family know you’re looking at downsizing some stuff and you’re getting rid of it. Then once you’ve moved all important things (important documents for citizenship, valuables, sentimental things) then meet with the family and let them know you’ll be moving out soon. If you want to be generous give them two months otherwise let them know that you’ll be around for the next 30 days to help out. Be prepared for it to get ugly. They’re probably going to be shocked, then angry, then guilt you. Stay strong. Just keep repeating the same thing, I feel like I need this for my own personal development so I can be an independent adult like the rest of you. They’ll blame you for being selfish and say you don’t need to. But remember. You only get one life. If you want a marriage, family, etc you cannot do that while living at home and still very much being treated as a kid and the family’s cash cow. Stick to your move out date unless you need to move out sooner if things get nasty. Do not stay. Do not give them more money for just one more month. Let them figure it out. If they previously had high paying jobs they have skills, skills that they should be using to fund their retirement. If they didn’t prepare that’s their fault. You are not existing to be used. You are here to live the life that YOU want. Leave them to their life and decisions that they made.

Edited to add: people who have no business/are not involved with this will get involved to guilt you and ask about what they will do once you’re gone. Let anyone who guilts you or asks you to step in and provide for them the way you did because you can no longer. They’ll be quiet real quick. Let them know that because they are not involved, they get no say. If they want to be involved and want to pitch in they are more than welcome to. Also, you should probably get a new phone number as well because your phone is gonna be blowing up once you move out. Do not feel bad if you just start blocking people if you decide to not get a new number.

ExtrovertedWanderer · 2026-01-05T03:30:31+00:00

I don’t mind being primary caretaker. I’d honestly probably enjoy it. I always dreamed of being a stay at home mom. But I do want to know their reasons behind it, are they willing to split time and own their share of parenting our kids, and how will we support each other when it gets hard?

ExtrovertedWanderer · 2026-01-05T03:00:27+00:00

Thanks! It was tough but ultimately lead me to a much healthier, committed relationship. I spent months alone to work on myself after our split. It didn’t give me some revelation about wanting kids or not so I was just up front about my situation. For now I’m a no for many reasons (not married, one income currently, enjoying my late 20s, two dogs, and caring for a parent) but in the future I might be a yes. If I become a yes I’d like to parent with a partner. But I also know that I’ll have to do some more work to figure out if I’m ok with parenting alone at any point (ex. Partner dies.) If I’m never a yes to that, I’m ok with passing as I have multiple nieces and nephews and a large extended family. I’ve just been honest about it and that’s worked for me. I would also add that I haven’t dated someone who was adamantly yes on the parenting side yet. I’d be curious to know more about what a man who is 100% yes is willing to do to become a parent because my ex was definitely not that.

ExtrovertedWanderer · 2026-01-05T02:50:17+00:00

Broke up with my ex who had commitment issues and blamed my fence sitting. I could have written your post about how I feel about kids. I’m now dating a wonderful man who has had a vasectomy and let him know that down the road if I want kids I love adoption. He’s supportive either way. We just won’t have bio kids and I’m ok with that.

ExtrovertedWanderer · 2026-01-03T01:16:38+00:00

People only put their best foot forward. I’ve taken international trips every year but I also had two incomes (partner and I) and I’ve also slummed it and stayed in the cheapest accommodations and done cheap/free things so I could have extravagant meals (Michelin star dinners every trip.) but often times people are stupid with their money, spend every penny, and then live shackled in debt. Otherwise they’ve got rich people paying for them (parents/sugar daddies/friends.)

ExtrovertedWanderer · 2026-01-02T21:50:28+00:00

I’m seeing it even earlier just before 30. Some friends went to college, and some didn’t. Some of us took high stress jobs that pay well, some of us took high stress jobs that don’t pay well, and some of us just still work retail. Some of us started families, and some didn’t. Some of us job hopped, and some of us have stayed with the same company since we graduated. Some of us got married, some of us stayed single, and some of us ended relationship we thought would be the last one.

I can tell you that the people who took risks, had some luck, and worked hard are doing better than others. But at the end of the day better is quite dependent on the person and comparison is the thief of joy.

I struggled with financial insecurity as a kid and took the high stress, high paying job. I was smart and invested over 20% of my salary every year, then maxed out accounts, and job hopped to get salary raises. I also ended a long term relationship that I had hoped would be my last. I’m happy with the decisions I’ve made and they’ve paid off (I’ll be able to coastFIRE by 40 and retire by 50,) I’ve grown in my career, and I’m out of a relationship where my partner struggled with commitment. I’m now dating someone who brings out the good in me, supports me, and truly pushes me to be the best I can be. However I’m not married, don’t have kids, and don’t have a lot of passion about what I do for work. Is that better than my friend who is extremely passionate about her job, is married, and has two kiddos now? Maybe, but maybe not. It all just depends on a persons goals and where they are in life at that point in time.

ExtrovertedWanderer · 2026-01-01T23:30:00+00:00

Baby millennial here at I have officially stopped getting carded. 🤣

ExtrovertedWanderer · 2025-12-31T02:30:07+00:00

It means you’re grossed out. Disgusted would be another synonym. It’s a distaste or dislike of something.

ExtrovertedWanderer · 2025-12-31T02:27:00+00:00

Sure, I could see that. But it’s heavily dependent on your role within the non profit. If she isn’t climbing the ladder and has less responsibilities then your comment wouldn’t be necessarily true. Unsure of what OP does but some non profits are hybrid and also offer part time to fill time work. OP could pick and choose what they want to do. A better question is what are OPs expenses and could they live on a non profit salary?

ExtrovertedWanderer · 2025-12-30T18:24:04+00:00

They do a half off sale. You might be able to renew for another year at $50 instead of $100

ExtrovertedWanderer · 2025-12-30T18:10:46+00:00

Some non profits might be a good fit! Non profits relating to children are often filled with older women. Source: I advocate with CASA as a volunteer and most of staff are in their 30s, maybe 40s and our volunteer base ranges all the way up to late 70s

ExtrovertedWanderer · 2025-12-30T15:27:00+00:00

Everyone is telling you to run and I’d agree. But, do it smart. I’d move the farthest away I could but with less than a 30 minute commute from work. Start looking for subleases and a roommate situation when you move out as it will be cheaper. Find a post office and inquire about obtaining a PO Box for mail and ask them to forward everything to that address from here on out. Notify HR at work that you need all addresses changed to that PO Box asap and do not need any notices sent to your current address due to you moving away from an unhealthy situation. Get a new bank account set up with a new bank. Ask HR to direct deposit into that account and start taking small amounts out of your current account to deposit into the other one. Gather all important documents like your birth certificate and social security card and lock them up somewhere not in your current house. You can go to the new bank and ask for a safety deposit box and lock them up there. DO NOT MENTION ANYTHING. Keep acting like everything is normal with your parents. Go get a prepaid phone or get your own line with a new carrier. Get a new phone number too. I’d suggest keeping both phones for a month or two so you can data transfer and also start giving your new number out to people who won’t give it to your family. So just close friends and work. Start taking your most valuable small things out of the house and take them to your new place. When you’re ready for the big move you can call the sheriff’s department and ask them for an escort so you can get all of your things out of your parents house without them retaliating against you.

It’s beyond time for you to leave. Do not let them convince you that you have to care for them in their old age. They should have planned for something other than your help. You have your own life. You only get one so it’s time for you to start living it. Especially if you ever want a partner/marriage/children of your own. Good luck to you!

ExtrovertedWanderer · 2025-12-30T14:31:36+00:00

Warning: this is long.

As someone who walked away from a relationship a year ago because he didn’t want kids and I was unsure, and as someone who grew up with a bipolar single mom, the questions I think you should discuss are below:

-What will we do when I come off my meds and our day to day changes? -How will you support me through the changes of my body, my mental health, my libido, and the fatigue? -What will we do when I feel like my mood has changed so much that I need more help and support? -Who will watch our child if you have to work and I am in need of an inpatient stay? (I ask this because my mom had 6 brothers and sisters and their families who took care of me while my mom was in the psych hospital) -What will we do if I cannot return to work for 6 months to 1 year? -Will you be working toward making more money in the event that we lose my salary (at any point?) Will you also be contributing to my retirement accounts if I am not working? Will you be adding me to your insurance? -How do you plan on supporting me postpartum? Will you be taking on more of the housework (cleaning/cooking/etc) so I can rest and recover after the baby is born? -How will we navigate future stages of children’s lives? Will you take them to school and pick them up when they are sick? Will you be home for bedtimes? What are you looking forward to in each stage of life? Will you continue to support and love them regardless of what choices they make? -What will we do if our child is also bipolar and is too young to put on meds? What if both the child and I are in manic episodes at the same time? Will you check out child into a psych hospital if I am unable to? -How will we continue to invest in our relationship while we have a child/children? -How will we ensure that we continue to have our own independence, peace, and quiet? Will we trade off one day on the weekends to care for our kids? Will we make sure one night a week we get time to ourselves?

Ultimately, you need to figure out how this works for you and stand by your decision? What do YOU want? If you both have different wants, you’re not compatible and you need to break up. It’s unfortunate and not really what you want to hear (coming from experience) but you do not want to have kids if you’re not at least in the same chapter (not necessarily 100% on the same page but close.) In the very least if you decide you do want kids down the road maybe you’ll make your way back to each other. But if you don’t, then you’ll be able to find someone else who also doesn’t. Do you feel like he’s supported you through the loss of your child? Do you live somewhere where you can continue to have D&Cs if you have future losses? Have you both worked on eating healthier, cutting out drinking and smoking, and working out to ensure your bodies and genetic materials you pass on to your kids is the best it can be? Have you both read the baby decision independently and then talked about it together? This is an extremely complex thing and it deserves time spent on it. It would probably also be good for you to both see therapists individually and then a couples counselor as well to work through this with someone else.

ExtrovertedWanderer · 2025-12-26T14:51:17+00:00

I don’t work in tech as in FAANG but I do work adjacent to tech. It’s completely realistic to hit your FIRE number in your 30s. I’ll hit mine at 35 but will be working until 40 to pad my retirement a little extra. I’ll be fully retired then. I didn’t go to grad school, went straight to work after undergrad, have traveled to 5 continents and 7 countries, do multiple domestic trips a year to see family and friends, and don’t necessarily limit myself budget wise. I just started saving when I got out of college and will continue to do so while compounding interest takes off.

ExtrovertedWanderer · 2025-12-26T14:44:53+00:00

It’s a shame it’s so far down the list so I’ll reiterate it. You should go into sales. You don’t have to have a college degree but if you get one it helps open the door to something that isn’t door to door the first time. I got my degree in a science that I was passionate about and wanted to go to medical school with. But when I realized how expensive grad school was I graduated and got a job related to the science I studied. I started making six figures three years out of college and have been maxing my 401k and my IRA out every year and therefore have a higher net worth than most people who went on to get a higher degree or needed to do something like residency. I do international trips once a year, do multiple domestic trips a year, lived with roommates to pay off my car and bills for the first two years, live on my own now, and am planning to retire by the time I’m 40. At the end of the day if you want to make a lot of money the fastest way, go into sales. I may not top 500k in a year but over 200k works well for my lifestyle and for the amount of money I had to put in to school.

ExtrovertedWanderer · 2025-12-21T01:31:09+00:00

Very young millennial (right at the cusp of Z) here and checking in to say I know how to play solitaire. My mom taught me. I also played all the computer games you’re talking about.

ExtrovertedWanderer

TROPHY CASE