Hi Stefanie!
This is a great question. I’ll try not to be too long-winded with my answers. 😉
So, first, I really recommend that you come up with a list of non-negotiables before you start job searching. These are things that you are unwilling to settle for less than; things that are key to your ability to enjoy your job and not get resentful of it. These could be any number of things — How long your commute is, your salary and benefit requirements, a solid work-from-home policy, a manager you can trust, etc. You can base your list off of things you’ve experienced in the past (maybe experiences you’ve had that cemented what you DON’T want to happen again), as well as what you know about yourself and your needs as a Thriver/Side Hustler.
Keep in mind that when I say “non-negotiable,” I don’t mean “the baseline of things you’d be able to accept.” I mean “non-negotiable” to your happiness and contentment in a work setting. There’s a big difference! Try to make this list without getting wound up about whether all of your non-negotiables are possible; if you know it’s critical, put it on there.
So, knowing your non-negotiables will help you have a baseline to job search from. I ABSOLUTELY want you to keep an open mind and about the possibility that you could very well find a position that aligns with all of your desires. I don’t want you to settle for something that you didn’t really need to take, only out of fear that what you wanted wasn’t possible. It is! We may not be able to control the timeline of when you find that kind of position, but it IS possible.
And definitely DON’T apply to anything that doesn’t align with your non-negotiables. If you know, just based on the job description or the way the company talks about themselves, that you’d be miserable and resentful really quickly, it’s not worth applying for.
However, there may be a grey area where a job will meet your non-negotiables, but you’re not sure if it’s a dream job. In that case, I definitely recommend (especially in an interview setting), asking about their values around the things you care most about (like flexibility). Kristen wrote an article about this for the Muse that you may like: https://www.themuse.com/advice/the-one-interview-question-you-need-to-ask-if-you-want-to-land-the-perfect-job
In general, I’m a big proponent of being honest and transparent and blunt in interviews. You don’t want to be hired as someone you’re not. And if they don’t hire you because you had the audacity to ask about something you care about … then you likely weren’t going to be happy there, anyway. My take is that you can’t mess up a job that’s truly right for you, so you may as well ask!
It IS possible that you could get hired and then ask for what you want, on the back end. But in that case, it’s really important that you have a good understanding of the company’s culture and values before you take the job. If they generally come across as open-minded, thoughtful, and put their employees first, then it’s definitely possible that they might be more lenient than they advertise up front.
Also, if you’re looking into a company, it’s worth checking out if they’re on Glassdoor. That’s a good place to see what employees have said about what it’s like on the inside. It can sometimes be hard to know if how a company describes themselves is actually how things are, on the inside!
I hope this was helpful! Let me know your thoughts. 🙂