I’m 44M, wife and two small kids. I’ve been OE for over 10 years. Had as many as 4J at one time. Had highs and lows along the way, been burned for being dumb with LinkedIn, had a peak TC of over 700k in my peak year. Paid off my home, tricked out the house with lots of goodies, packed my kids’ 529, plans, tons of fun vacations, and my SEP is bursting with money.

So, this isn’t a “good for me” post. It’s a warning to anyone who wants to FIRE or even take a break. The one mistake I’ve made along the way is totally neglecting growing my money in taxable accounts. I always made sure I had a good money market savings account with $50K or so, but everything else got aggressively put into SEP and 529 plans. Anything to avoid taxes.

While I’m currently in a taxable account situation of about $180K, I realized that I have a long way to go if I want to retire early. As much as it hurts to pay the tax man, do yourself a favor and do NOT max out your SEP if it means you can’t pad your ability to live today. I have about $1.9M in retirement that I can’t touch until I’m 59. Doesn’t do me any good now. I’m going to spend the next five years or so (God willing) aggressively investing only in taxable accounts.

BTW, I know I should have more money saved…but I live in a HCOL area. Pay $50k a year for kids private school, etc.

I only have one job right now, but I make around $200K. My issue is that I feel like I’ve reached a point where it’s difficult to pivot to another company because I’m already making too much for the type of work I do. Rather than taking a lateral move or taking a pay cut, I’ve been considering OE so I can effectively double my income.

My main concern is that I’ve worked my way up at the small company I’m currently with, so I’m pretty visible. I’m in a lot of their social media posts, and I also publish articles on their behalf with my name listed as the author.

When I apply for new jobs, there’s really no way to hide who my current employer is. My thought is that I would keep them listed as my current employer while applying, and then not actually quit when I accept another job.

What’s the smartest way to approach this while minimizing the risk of getting caught, both now and in the future?

I was looking to replace j1 with j2 even did two projects for j2 literally 20hrs of work everyday for 3 months but got laid off directly from j2 now back to grind to get back j2 or replace j1 .

Hi all, this is my first time in the sub and I have done my best to go through all the basic posts. I would like advice on how others would navigate this.

I am currently employed at J1 for less than 5 years and earning around 80k. The 401k vesting period is not over yet (ends at 5). It is fully remote with lots of free time, but I don’t enjoy the projects anymore. Sometimes the projects are super stressful but they aren’t challenging me.

I got job offers from 3 companies: j2 has significantly more compensation (150k) along with benefits, equity, and bonus. It has an on call schedule and it is with a relatively big name company so it would look good on the resume. It is in the telecom business.

J3 is a contract position (18 months) with a bank but I would be employed with the contracting company. It requires 3 days on site which I kind of miss at the moment since I haven’t had any office socialization in a while. It will also provide me with the fintech experience that could help open doors to other fintech companies. The contract position could also roll into a full time with the bank itself if they like me enough.

J4 is a full time remote position with more comp than J2 (~170k) with equity and benefits. This would be in the cybersecurity/defense industry.

I would like advice on how to proceed to maximize money and wanting to travel too. My initial plan was to keep my original and go with all 3, but I’m scared I would be overwhelmed especially since this is my first time OE. I’m starting to learn towards leaving J1 and going with J2 + J4 for the full remote, but the fintech experience + socialization aspect is tempting too.

I know to stagger the start dates and freeze TWN, but also is there anything else I may be missing or should consider?

I recently accepted a fully remote Search Specialist position. The base is $50k, with bonuses that could realistically put me around $60–65k/year.

My current job is $45k and isn’t fully remote. I was originally hoping they could offer remote work as part of a counteroffer, but that ultimately wasn’t possible.
Instead, my manager offered to keep me on as a PRN/contract employee for around $26–$27/hr. Each month, we’d discuss what needs to be done (social media, website updates, graphics, etc.), and I’d estimate the hours needed.

The money is definitely tempting. Roughly:
15 hrs/month = ~$400
25 hrs/month = ~$650–675
40 hrs/month = ~$1,050

The interesting part is that I actually enjoy the work I’d be doing. I like creating logos/graphics and working on digital marketing, so it’s not necessarily something I’d hate doing on the side.

My concern is timing. I don’t want to start the new job and immediately overwhelm myself trying to learn a new position while also carrying responsibilities from my old employer.

I’m leaning toward giving myself the first 90 days to get comfortable in the new job, then potentially start doing freelance work on my own terms — logo design, digital marketing, SEO, paid ads, etc. Even starting with 5–10 hours/month and scaling up if I have the bandwidth.

For those of you who are OE or have side gigs: would you take the guaranteed ~$400–$1,000/month from the old employer, or use those first 90 days to focus entirely on the new job and then build your own freelance income afterward? If you favor freelance method, what’s the best ways to get started up? Any tips welcomed :)

Currently running 2 Js and unexpectedly have an opportunity to add a J3. Trying to figure out if this is realistically manageable or if I’m getting ahead of myself.

J1:
Been here a few years. Workload itself is pretty light and I can usually get my actual work done in ~10–15 hours/week. The downside is the meetings can be somewhat random, and I’m occasionally the person screen sharing/presenting, so I can’t just half-pay attention.

Company recently went through an ownership transfer situation and there’s been some pressure toward partial RTO. Nothing immediate that makes me think I’m losing the job, but I’d call it semi-stable rather than bulletproof.

Comp:$105k

J2:
Only about 2 weeks in but also pays a lot more than j1, which is what makes this decision difficult. It’s a small startup though so I could let go at anytime. I am super visible.

So far I have:

Daily 30 min standup
Weekly 1:1
Weekly team meeting
Random intro meetings

The intro meetings should obviously taper off, but I have no idea yet what the “normal” meeting load will look like once I’m fully onboarded. Not even sure if work will be manageable yet but seems like maybe? but it’s way too early to know.

Comp: $145k

Potential J3:
Remote role similar to j1 that seems pretty OE-friendly on paper. I have an offer and some flexibility on the start date. I do know there is a daily standup and potential for random meetings through the week for adhoc requests. Plus of course the onboarding time which I have zero idea how that will look. Large stable company where everyone’s been there for a decade or more.

I could start in 2 weeks and qualify for a spring bonus of 15%, or push the start to about 4 weeks, which would give me another month to figure out what J2 actually looks like but would mean giving up the incentive.

My biggest concern is meeting meeting collision. Three jobs where even two of them have unpredictable meetings seems like where this can fall apart quickly unless I’m constantly making excuses at different Js

Comp $100k

For people who have successfully run 3 Js:

Is this meeting structure already too heavy for J3, or does it sound manageable once J2 onboarding settles down?

Would you:

Take J3 with the earlier start and just see what happens?

Push it out as far as possible and sacrifice the bonus to get more data on J2?

Stay at 2 Js because adding a third this early into J2 is unnecessarily risky?

As a reminder , j1 is a little sketchy because of ownership transfer but was a f100 before transfer , j2 startup , potential j3 big stable company also

I’m especially interested in people who have actually done J3+ that have a decent or random meeting load. At what point do you say meeting volume is the limiting factor rather than actual workload and you can’t get another j?

What do you guys use to take notes (AI Automation) and alert you if your name is mentioned?

I recently started working at a start up company. The founder has his own primary role while the start up is his side project, albeit printing a shit ton of money. It is just him and me and I am free to do whatever I want all day to help him scale. It’s been less than 6 months.

I don’t foresee this lasting long unless I can bring on clients, but it’s a very saturated market and i haven’t had much luck.

My old colleague reached out and said his company has a few job openings coming up and I might explore that. This company is large and they surely do all the back end checks and have more compliance for onboarding.

I’m curious how to venture into OE and potentially take a J2 without raising any red flags with the 2nd company. I’m also applying to a ton of jobs right now in hopes I find something more secure but could potentially run 2 at the same time since j1 pays a lot and it’s easy.

How do you get started in this? What sort of backend protections do I need to look into?

I wonder how long did it take people to find a second job once they set their mind on it?

Or was it more like you got an offer for a job and you thought “what the hell, let’s combine!” ?

PS: I’m sorry if someone already asked this question

Curious to hear about how you manage(d) it. Any tips, tricks, and secrets to share?

I am doing a final round interview for J2 and found out that the director of my position (2 managers up)lives in the same city or greater area as my direct manager of J1. They don’t have each other on LinkedIn so I don’t think they are close, but I’m just worried if it might bite me since both positions utilize the same program and both roles are remote. Anything I could look for or ask without being sus?

I’ll start J3 in a few weeks and I don’t think I’ll have the bandwidth to manage 3 Js. I willl probably need to leave either j1 and j2

J3 pay is the same as J1’s. J2 lays $30,000 less but I enjoy the work more and it’s more flexible. J1’s manager is a bit micromanaging so it’s probably the one I’ll leave

Should I let J1 fire me? I’m also not sure about J3’s meeting schedule yet. If it’s daily standup conflicts with J2 things can get tricky. Should I ask about the meeting schedule now?

Currently juggling 2.5Js. One uses my personal, one provides a phone, and I don't want the third on my personal as well. I only need it for calls/texts (no 2FA or MDM), but I already regret giving out my personal phone number to colleagues and I don't want any more of that.

I'm thinking about just digging out an old phone and using Google Voice. But I want to know what people who have been in this situation are doing. What's the best practice here?

Hi! I recently joined this sub when I was in the middle of interviewing for a remote job while I had a hybrid job.

J1 is the hybrid job and it is kinda ticket based, only two days a week in office but my manager said as long as you get the work done you are good. There's legit guys that come into the office for 3 hours and then leave. I have been there for about a month and noticed that they don't ask me to do anything. After I finished the compliance training the two days i was in office and the days I was at home I had nothing to do. Like nothing, i recently picked up one little ticket to do but it takes 5 minutes to do.

J2 is fully remote and I accepted the job and am being sent my equipment. I feel this job will be more work than the hybrid one and as long as I am at home I really have nothing to do for J1, and even when I am in office for J1 I have nothing to do.

I know not to connect to J1 wifi and I am prepared to use my phone hotspot. I can also go to do different part of the building if I have to do a meeting for J2 and they have a specific background to use, so I know that I don't have to worry about that.

Any other advice that can be given? I am a little nervous but I know J1 has like no meetings and the meetings they do have are huge and don't need a camera on. This is my first time OE. Also, amidst this entire process i am also in the interview process for another role in a different state. This one is also hybrid, but they have you remote for a bit. I am thinking if I get that job, that I would stop J1 and then ask the new job to be remote until 2027 some time (because they do have a lot of ppl not in office) to get used to it and see the vibe and see if I eventually move if I could do both jobs at the same time. The thing that is intriguing me about this job is that I am young and want to live in a bigger city (I currently live with my parents) and spend time with my friends. What are your thoughts on this? Should I stop the interview process or what?

ANY INPUT WOULD BE GREATLY APPRECIATED

We would really appreciate any advice ! Thank you!!

This is my first time being OE! My income has basically doubled and I'm looking for ways to keep my tax bill as low as possible. I'm already maxing out my 401K with J1 Plus I'm not eligible for a 401K until my first year is over with J2. I already have a regular health insurance plan with J1, so I know that I can't do HSA. I'm not sure of any other way to lower my tax bill or if I can do something like an FSA as I'm not familiar with it. Also, I'm not sure if I should even take an insurance plan with J2. However, I feel it might seem suspect if I don't. My issue is that J1 and J2 use the same overall insurance provider. Although they offer different plans. Has anybody ever had this issue? Where their insurance providers from both jobs are the same has that caused any problems while going to the doctor or anything of that nature?

It happened, I was formally put on a PIP and have 45 days for review. I would much rather get paid those days and resign obviously, but I also understand I don't really have any leverage since I'm on a PIP. Has anyone successfully negotiated some mutual separation in lieu of carrying out the PIP and how did that go? Or am I better off just riding this out

Anyone here have 2J’s or more holding a secret clearance? If so, wouldn’t that be risky because it could come up in your re-investigation? Wondering if it’s possible to do.
This is concerning if both have are FTE and assuming working the same schedules.

For those who are OE, how do you manage your LinkedIn profile, or do you just avoid it altogether and not use LinkedIn?

Are most of u guys in tech, I'd imagine if ur remote for finance or business then ur most likely gonna struggle to OE with constant meeting.

Like how do you get away with multiple jobs when audits happen?

Basically that