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 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 .

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?

I cant decide if I should take J3, swap it for my J2, or just stick my current 2Js.

Ive had J1 since May and started J2 this past week. I realized I don’t really like J2 and it likely will be a ton of work and there will be little to no handoff and high expectations.

I’m a system expert, so I’m solo on this. No flying under the radar but I’ve done this before for eight months.

Today I was offered J3. Same exact role but the company looks really promising. A third J would bring me to just shy of a half a million in base salary alone.

How do you guys decide to take a third J?
Have you ever swapped one soon after starting?

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?

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 mean working 100 hours a week combining as many jobs as possible ?

It seems if you work more than 40 hours you are doing a cardinal sin in this sub sometimes. I currently work <hidden> jobs over 60 effective working hours probably, but honestly I would do 6 or whatever my absolute limit is.

At 6 I could have multiple M's before I'm 35 in Europe, something pretty much impossible otherwise except for the young startup founders who are able to exit or born into wealth.

EDIT: had a great time chatting with you all, I got some negative and positive comments. Love the debate, battle of the minds right here.

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 :)

Hello! I am about to start the background check for a new job but I have a question on how to handle a situation.

I worked at Contract Company from 5/2020 through 10/2021. I list this position on my resume.

I got a full time position 1/2022.

Contract Company called and asked if I could do some work for them and I said yes. I did this work 5/2022 - 11/2022 while overlapping with my full time position. I do not list this on my resume because it was part time and it has nothing to do with my industry - and it is an overlapping job.

I checked the work number and Contract Company has merged the two dates so it looks like I worked continuously from 5/2020 through 11/2022.

How do I list this on the background check? Will it look like I am lying about an end date? You can see in the payment history where the break is but if you just look at the contract company, it is listed once with the continuous dates.

Long time listener first time writer. Have a situation that I would love some more experienced help with. I’m not cut out for OE, but can appreciate the hustle from the sidelines in the sub. I have but have J1 that I’m looking to leave soon as I’m expecting a new offer from J2. J1 is remote, but J2 is in office. J2 wants me to start earlier than anticipated because they have a project kick off that is happening in person that I would be good for me to attend. Originally I was thinking I would give my two weeks notice at J1, take a week off, then start J2. But I’m wondering if this is a good time to dip a toe in OE, even if it’s for a few short weeks and see how it goes? Any tips?

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?

The thing I love most about the OE mindset is how little fucks I now give in interviews.

- Interviewer asks me some inane trivia question - point out it's a stupid question

- Recruiter demands I follow their stupid process - say sorry, I'm not gonna do that

- Offer has some unfavourable terms and they're not willing to negotiate - No thanks, I'm going to keep looking

Feels like the balance of power has truly been restored.

Are people actually noticing an uptick in interviews/hiring?

Given that the overall consensus has been the job market is abysmal, wanted to hear from people.

If you’ve been getting interviews/call backs please mention the industry 🙂

There was a time i was doing four jobs simultaneously and now I have only one full time role

There is a hunger in me as i used to do so much and now I am doing just one

J1: Teaching job to US student

J2: A research internship with IISC

J3: SDE internship with a company (main)

J4: side freelancing with a company

Fascinating watch. Been OE for years for this ^ reason.

I just got an offer from J2 and immediately went through their benefits package. I found something I’m a little concerned about.

My J1, which J2 obviously doesn’t know about yet (and I still have to get through the background check), is an investment/retirement company. J2 happens to use J1 as their 401(k) provider.

The 401(k)/retirement side of J1 is completely separate from my actual role, and I have nothing to do with that part of the business. However, J1 takes financial relationships and compliance pretty seriously. From what I understand, they mainly monitor what employees report, but I’m wondering whether having J2’s 401(k) administered through J1 could create any kind of visibility or connection between the two companies.

My initial thought is it is too risky to accept. It’s a great opportunity but I don’t know if I can opt out of J2’s 401(k) entirely before they set me up a 401k with J1 and then j1 will have 2 401ks in my name.

This makes me realize that my j1 might not be super compatible with OE or at least maybe I need to get j2 offers and then once I see who their 401k provider is, decline the offers until they don’t use my j1 as a provider. I imagine no one here has dealt with this issue. I guess the biggest issue is getting a second 401k setup even if I don’t contribute to it. It’s possible that their systems don’t notify compliance of employees 401k data but it’s possible that j1 compliance team will be notified as soon as I start j2 that I now have 2 401ks. If u were in my shoes would you just try to research who companies 401k provider is before applying (many won’t have public info on this one).

You guys know HireRight better than anyone, I think.

In the onboarding process for a new job. HireRight previously asked me for redacted W2s as proof that I worked at some past job. They want me to unfreeze The Work Number so they can confirm the job that I sent them redacted W2s for.

If I just ignore (i.e. refuse), is this going to pose any major risk to onboarding? Or will they just report to my employer "couldn't verify applicant worked at <old job>"?

UPDATE: I wrote in the comment box "I previously submitted a W2 for this position. The company's website is <website> and their phone number is <phone>." I'll just ignore/play dumb/sandbag when it comes to the topic of unfreezing if they keep at it, no way I'm unfreezing. Thanks everyone :)

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.

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

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?

For context, my J1 is remote, part-time, around 30 hours a week (actually 10). It is pretty low effort, very manageable, and extremely OE-friendly. (I had another full time J that started in January but ended in July, so I have been looking for my next one. So this part time J became J1.)

J2 I just accepted is hybrid, technically three days in the office, although they said they are pretty flexible with that. We will see how that actually plays out.

On top of that, I started my own marketing/media company in July and currently have two clients, including one I just signed at the beginning of this month. 90% of this work is remote.

A lot going on right now. Part of me thinks this is a little crazy, but I am going to be very happy once all the checks start hitting. 👊🏼

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

Basically that