tldr; friend is working a caretaker job whose employer is a tech lead and is interested in giving her work in 2-3 months. Other option is to take her return offer (RO) from her startup immediately (even though the startup is failing and has ~1 year of runway left). Should she take the caretaker job for 3 months or take the startup job? I was talking to a friend who’s in a strange situation right now and I’d like some advice. The story is basically She got an RO from her startup but no other job offers. While she likes her coworkers, she doesn’t like the startup itself as it’s doing poorly. She expects the startup to have 1 year’s worth of runway. The return offer is flexible - if she asks HR that she wants to come back then she can show up the following week to work. There is no deadline for this RO Besides the RO, she got this job as a caretaker and her employer is a tech lead at a stabler company. She’s already signed the contract for this job. The tech lead said that they’re actively hiring and that they have some data analysis work that needs to be done that matches her skillset well, but the data needs to go through some compliance that lasts for a couple of months. She has several plans right now: Plan A: Work the caretaking job + take her return offer as a remote position (need to negotiate for lower pay since startup doesn’t really like remote work), apply to jobs on the side Plan B (Assume that she can’t negotiate remote work) Work the caretaking job + apply to jobs + do side projects + interview prep aggressively If her caretaker employer doesn’t have an opening by 3 months, she goes back to her full time job. At least from my analysis, here’s the worst and best case analysis: Worst case: She doesn’t find a new job in 3 months, her caretaker employer doesn’t have a job for her - she returns back to her startup Best case: She finds a new job or her caretaker employer gives her the job - goes to that job instead So the worst case doesn't seem that bad, whereas the best case can get really good. So would skipping out on 3 months (5 month gap since graduating) of professional experience really hurt her candidacy for future jobs? Wondering if this is a viable strategy, or if there are better ways to approach this?

What's a caretaker job? It seems like a contracting position, but when I think of caretaker, I'm imagining someone working in an elderly care facility or something. Plan A seems rough as you would be working 2 jobs at once? Honestly, 1 year is a long time. The startup return offer isn't bad - I would take it. Your 1st job is often just 1 year long (like my stint at PayPal), and the economy should hopefully be better after the 1 year. You'll learn a lot at an early-stage startup, especially if you play a major role in turning it around. I'm actually leaning towards just returning to the startup unless the caretaker job has very clear criteria to convert into a more full-time position.

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tldr; friend is working a caretaker job whose employer is a tech lead and is interested in giving her work in 2-3 months. Other option is to take her return offer (RO) from her startup immediately (even though the startup is failing and has ~1 year of runway left). Should she take the caretaker job for 3 months or take the startup job?

I was talking to a friend who’s in a strange situation right now and I’d like some advice. The story is basically

She got an RO from her startup but no other job offers. While she likes her coworkers, she doesn’t like the startup itself as it’s doing poorly. She expects the startup to have 1 year’s worth of runway. The return offer is flexible - if she asks HR that she wants to come back then she can show up the following week to work. There is no deadline for this RO
Besides the RO, she got this job as a caretaker and her employer is a tech lead at a stabler company. She’s already signed the contract for this job. The tech lead said that they’re actively hiring and that they have some data analysis work that needs to be done that matches her skillset well, but the data needs to go through some compliance that lasts for a couple of months.

She has several plans right now:

Plan A:

Work the caretaking job + take her return offer as a remote position (need to negotiate for lower pay since startup doesn’t really like remote work), apply to jobs on the side

Plan B (Assume that she can’t negotiate remote work)

Work the caretaking job + apply to jobs + do side projects + interview prep aggressively

If her caretaker employer doesn’t have an opening by 3 months, she goes back to her full time job.

At least from my analysis, here’s the worst and best case analysis:

Worst case: She doesn’t find a new job in 3 months, her caretaker employer doesn’t have a job for her - she returns back to her startup

Best case: She finds a new job or her caretaker employer gives her the job - goes to that job instead

So the worst case doesn't seem that bad, whereas the best case can get really good. So would skipping out on 3 months (5 month gap since graduating) of professional experience really hurt her candidacy for future jobs?

Wondering if this is a viable strategy, or if there are better ways to approach this?

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Discussion

(4 comments)

0
Alex Chiou
•Tech Lead @ Robinhood, Meta, Course Hero
6 months ago
What's a caretaker job? It seems like a contracting position, but when I think of caretaker, I'm imagining someone working in an elderly care facility or something.

Plan A seems rough as you would be working 2 jobs at once?

Honestly, 1 year is a long time. The startup return offer isn't bad - I would take it. Your 1st job is often just 1 year long (like my stint at PayPal), and the economy should hopefully be better after the 1 year. You'll learn a lot at an early-stage startup, especially if you play a major role in turning it around.

I'm actually leaning towards just returning to the startup unless the caretaker job has very clear criteria to convert into a more full-time position.
- 0
  Software Engineering Intern
  •Taro Community
  6 months ago
  What's a caretaker job?
  
  My friend's role as a caretaker is to take care of her boss' children. And yes, this is a contract position. The point is that this role isn't technical and the only way it "grows" her career is if her boss gives an offer to his company in 2-3 months
  
  Plan A seems rough as you would be working 2 jobs at once?
  
  I agree - it does seem pretty rough. On the other hand, it's only 2-3 months, so if she can tough it out, she can have the best of both worlds - (work experience + upside to better opportunities). So maybe a better question is what's the opportunity cost of caretaking vs spending more time either on her job?
- 0
  Alex Chiou
  •Tech Lead @ Robinhood, Meta, Course Hero
  5 months ago
  Oh wait what, she's literally taking care of people, not code??? Converting this into a technical job at a tech company seems incredibly suspect. I can't even imagine how this conversation plays out.
  
  Taking care of your manager's children is also a huge violation of work/life boundaries. This could go wrong in so many ways...
- 0
  Software Engineering Intern
  •Taro Community
  5 months ago
  Thanks for the response - and yes, I also felt that relying on the good graces of a tech lead leads to really tricky situations. It took a lot of convincing on my end for her to take her RO, and what you said definitely helped get the message across.