Should I stay or should I go?

[Giro]

Let's assume the pay is exactly the same.

Current role - I'm a supervisor getting beat up pretty badly on a weekly basis.  Things seem to be improving over the past few weeks and probably slowly steadying out.  The gig is minimal real work, lots of babysitting and ego-stroking.  The hours are crazy flexible and I have a lot of time off.  The company loves me and it would be tough to resign.

Potential future role - One person shop doing enterprise architecture for a legacy software system.  No one to manage, no one to be managed by.  This would be some tough work and maybe some late nights.

[ruraljuror]

Sounds like your current role puts you in a better position to have the most impact on people, which is more important than legacy software systems in my book. That combined with more flexible hours makes the current gig sound pretty good.

[pbkmaine]

Are you an introvert or an extrovert?

[Giro]

I'm an introvert.  I have decent people skills which is why I always end up with employees to supervise, but I get my energy alone. 

I'm going to try hard for more money in the new role and then I'll have more incentive to go.  I'm 600 working days out from FIRE.  I need a solid 2 years worth of work to get me over the hump. 

[plog]

First, know that in the future you will regret (on some level) this decision---no matter which one you make.  There will always be bumps down whichever road you choose and you will idealize the path not taken as being better at that moment.  In this specific instance I think either path is a good one, so I don't think you should think of this decision as a monumental one in your life--take some pressure off of yourself.

With that in mind, here's what I would do. Pick a percentage raise  you would be happy to stay in this job for.  Maybe its 10%, maybe 15%, that number is up to you.  Next, add 5% to it.  Let's call that Stay%.  Now, take the other job.  I literaly mean accept their offer and tell your employer you are leaving.  If your current employer position offers you Stay% or more, then stay.  If they say nothing or offer less, leave.  I wouldn't negotiate, I'd just have a solid plan for how to react if they do offer more money to stay.  Treat life like a chess game and think 1 step of the other guy--plan your counter action to their possible reactions before you make a move.

[sisto]

If it were me I would stay since it's getting better and you only have 2 years left especially with the flexibility, but I prefer security in my job. You also stated it would be hard to leave. Good luck with whatever your decision is.

[Axecleaver]

With that short of a timeline, you're better off staying where you are. So, the thing to do is to figure out what the new job would have to offer you, for it to be an easy decision to leave. Right now, it's tough. Then ask them for that.

From your description, it isn't clear if the new job would be you opening up your own business with a primary client, or going to work for someone who currently is a one man shop. Either way, there are some large risks and rewards to these types of arrangements. Payment delays, liability insurance, project risk. With 600 days on the clock, might be a bit late in the 4th quarter to start exploring these other options. So the payoff has to be there to balance the higher risk.