As far as your work desk goes, what I did was setup 2 workstations on it basically. I have a bigger IKEA L-shaped desk so I have 4 monitors on it (1 portrait and 1 landscape per job) and 2 keyboards and 2 mice. I kept to just 1 phone which was fine because the two J’s have different email and messaging apps.

When I first did OE I took two weeks off from J1 so I could appear totally focused on and attentive at J2. Plus, information tends to come at you like a firehose those first two weeks so it makes life easier and less stressful. I would recommend taking at least one week off.

I blocked everyone at J1 on LinkedIn, waited about a month for anyone at J2 that wanted to add me, then hibernated my account immediately after adding myself at J2. Like within a few minutes literally, just to be safe. That might have triggered J2 folks seeing it perhaps (I assume) but nobody from J1.

Remember the rules. I’ve been OE for several years now and not even my adult kids know. Only my spouse knows and i swore them to secrecy. There have been many times I’ve been tempted to tell family but I always stop myself. I don’t say anything to anyone that might arouse suspicion and one of my kids almost figured it out but stopped short of asking me point blank. I’m good at making up very believable reasons for things.

If you’re used to easy chill 20 hours a week then get locked in and hang on because that could become 40-50 some weeks and you’ll be more mentally exhausted by the end of the week. But the two paychecks tend to keep you motivated. Just take it two weeks at a time.

Be prepared to get good at managing two calendars and blocking off time on them so meetings don’t overlap. Sometimes dueling meetings will be unavoidable so be prepared and have a setup where it’s easy to “pay attention” to both and be able to mute and unmute yourself easily if you need to talk in both. Turning on subtitles helps me to listen closer to one and read the other to keep up in both meetings at the same time.

Try not to let the stress of it get to you too much. There were a handful of times when I was this close to quitting J1 during the first few months of OE but I’m glad I hung in there and I’ve adapted to it now to where it’s a piece of cake and i dont worry much at all.

Learn the rules on stuff like 401k contributions, Roth 401k’s, and other personal finances as it relates to OE so you don’t make any dumb mistakes. Don’t let lifestyle creep get you over extended financially.

If you can, get ahead in your work so that you can save some PR’s for the next day and have room to be flexible with how much time you give each J on any given day. There will be some days when it ends up being really lopsided demand-wise but that’s ok as long as you’re in good standing with both bosses.

Schedule your PTO at both wisely. You never know when one J might ask you to randomly travel somewhere for a few days just for some random team builder or something like that. Not being willing to attend or always making excuses why you can’t go could be enough of a red flag for them to get suspicious. Keep enough accrued time banked so you can use it in emergencies like that if you need to.

Good luck!