Should I stay or should I go?

I was depressed about my job and decided it couldn’t hurt to start applying to roles that really struck my eye, full well knowing that historically I’d apply to hundreds of positions before getting a few calls… and it would take weeks to hear back, if I ever did.

My plan was to stay at my current job at least until the end of December, so I could finish out my year and really wrap up the current projects I’m working on so hopefully all involved could look at my time at the company as a success where I clearly added value, even if it was time to move on. I figured starting to apply for jobs now meant I’d maybe have a few interviews starting in late September/early October, being drawn out through October, with the earliest I’d get an offer being late October/early November. With a little negotiating I could bump out my start date until sometime in December.

It was quite surprising when I applied to one very exciting role on a Sunday and received a call back on a Monday for the opportunity. I wasn’t so surprised that they were interested in me (my background is a great fit for the role) but more so how fast they responded. After the first call with the hiring manager, I was fast-tracked to the final round… apparently, they already had a few other late-stage candidates and wanted to get me in the mix. Just a week later I had a three-hour on-site interview where I presented to the entire team of very impressive people.  I think every single person in the company has a degree from an Ivy League school or a comparable quality technical institution. Their team page includes three bullets about every team member, and I just laugh to think of myself added to the page… with all my lack of accomplishments. Bullet one: graduated college. Bullet two: early employee of two startups that crashed and burned. Bullet three: did NOT get into any Ivy League Schools, or run any triathlons, or set any world records.

For some strange reason they still really like me. They are so damn smart that I worry I’ll fail to connect… I already am having this problem with a coworker who I very much so respect who constantly wants to punch me in the face because he’s so smart-as-fuck Ivy-trained engineer who sees things so systematically and my thought process is much less organized. I’ve worked with people like him before and I really do respect him, but I worry that this new company is just all people like that who say they respect creative types but then really are only interested in talking in their very formulaic language based on data-driven reasoning. I’m not opposed to that type of communication, and quite frankly, I prefer working with more logical people to a sea of creative as logical people are at least possible to understand, analyze, and interact with based on understanding how they process information (as long as I can keep my ADHD foot in mouth disease in check – unlikely.)

I mean, these people are really smart. Not just kind of smart. Like, “I got eight PhDs from Harvard” smart. I don’t fit in. at. all.

Could I pull it off and actually be successful in this role? Maybe. It’s definitely different from my past positions. I feel like even though it would be very hard it’s less stressful in some ways. It could be the opportunity of a lifetime (or, in startup terms, the opportunity of the next 2-4  years.) I don’t know…

My job is finally starting to go well and I don’t want to leave now. I wanted some more time to feel it out. This new job would mean a paycut, which I’m ok with on principal, but only if I really would be happier in it then my current role. I really think I’m starting to figure out this management thing and my team seems to like me and I also think I’m doing an ok job of mentoring them and helping them grow in their careers. That feels really good. I’m definitely more of a nurturing manager and I struggle with the more strict / constructive criticism side of things, but I definitely love to give my team opportunities to thrive and focus on their strengths. I’m finally getting the hang of it and good things are happening.

But is it too late to save myself here? Maybe. My boss still clearly plans to replace me as soon as someone better comes along. I’m not upset about that, I just wish he was more transparent about it. I felt very uncomfortable after my last conversation with him around my performance where one of the options he supported was my staying in the company for three months and saving some money while looking for a new role – that didn’t exactly send any signals of stability… it basically told me “look for a new role.” I don’t think I was reading into that too much. Maybe I was. Maybe he was basically saying either step up my game or I plan a transition out. I think I’ve stepped up my game. I’m by no means perfect, but I’ve been trying really hard. I still have a ton on my plate and that never ends, but maybe I’ve done enough good things where I’m no longer sitting on the chopping block under the knife. For now.

I don’t know what to do. I have to get references together for this new opportunity and have a formal offer letter come through if it is going to and then, well, negotiate and/or sign the offer letter or decide to pass on it. I can’t exactly go to my boss and tell him I have another job offer and I want to know if he thinks I should take it. Either I take it or I don’t. I’m not going to be able to keep things status quo until the end of the year like I had hoped and intended while applying to the job. I just didn’t think this would all move so fast.

I have a lot to think about this week. Maybe I won’t really get the offer anyway. The whole process has been weird. I’m normally much better about negotiating but this time I haven’t put much energy into it. They told me the range for the role, I told them what I’m currently making and put the ball back in their court. I don’t think they’ll match what I’m making or come that close to it, but I made it clear that I’m looking for the right opportunity and willing to bring down my salary expectations a bit for a role where I can really do great work.

The other concern, though, is Mr. HECC is going back to school next year to be a teacher and with his starting salary at $48k if he even gets a job right away, I need to make a lot of money for us to stay here. I mean, if they offer me $160k that’s still very good… but with Mr. HECC that puts us at “just” under $210k a year. That’s tough. With my current salary we’d be closer to $250k, which I think is the bare minimum a couple can make to be able to afford a decent life in the Bay Area. Really $350k-$400k is ideal for a basic middle class life here (about $18k-$20k take home per month after tax). I don’t think it makes any sense to give up a job that pays more, has certain maternity benefits due to its location and size, and one where I am at least going to have a year under my belt at the time I have a child.

I don’t think  I should leave, even though I may regret not leaving. The new opportunity has so much going for it… a lot of challenges to, but it’s just really special and I want to be smart about this decision. But today, most of me wants to stay. When I applied for this new role, I was so upset and felt like I couldn’t succeed and saw another candidate being interviewed for my department without my being involved in this. I can’t handle the stress of not knowing where I stand, and I don’t think I’m going to find out beyond actually doing an amazing job and just being temporarily irreplaceable.

I’ll proceed with hopefully getting the job offer, then I have to figure out how to deceifer my current job security without telling my boss I have another offer… and figure out if I should jump ship now or just wait it out and hope that I can manage to capture a few more months/quarters of job security while also delivering some incredible results.

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