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Honestly I did not wait. I did IVF with number one and had repeated infertility with number two that resulted in 2 losses and an additional failed IVF. During that time I also found my job/commute incredibly stressful and left and found a new job. I then did a Hail Mary IVF right before starting the new one and it worked. Honestly it was super awkward for me and they only wanted me to take 4 weeks (although my doctor wrote me out for 8 bc of a c-section).

That being said, I would do it the same way again. Even though pregnant, I had almost 9 months to prove myself a hard working and valuable employee. Plus I managed to have two observations (reviews) before I announced the pregnancy. So even though I felt terrible leaving so early, it was necessary for me because the not knowing how long it could take, crossing into AMA, and losing the spacing I wanted between kids was affecting my overall mood/life. I just felt I could not put it off anymore. So I think it depends if those are factors for you as well.

@dc yoga bee: are you working in DC? If so, wanted to make sure you knew a company only has to have 20 employees for DC FMLA eligibility.

I'd probably wait 3 months so that you will have been there a year if you are lucky enough to conceive right away. I wouldn't wait longer.

You could still check to see if your state has any requirements for maternity leave. I work for a tiny company and our state had a requirement for 8 weeks unpaid (I negotiated it to 12 weeks).

I would check the specifics of the STD benefits and try to make sure you can qualify for those. When I got pregnant with my first I found out the same week I got a new job as a contractor.

I had been unemployed after a layoff and I was determined to live my life. I had to go through infertility treatments too, and it seemed to be silly to wait until I had a job when I wasn't doing anything else. It all worked out in the end. My company hired me full time about 3 weeks before I had DS and I qualified for STD right away.

To clarify, you're worried because you'd be taking leave with zero guarantee of being able to return to your job, and so you're thinking if you work longer beforehand then they're more likely to decide to hold the position for you? Is that right?

Just throwing this out there - I work for an FMLA-exempt company, and they offer an equivalent benefit anyway because it's the right thing to do and they want to be competitive for talent against bigger companies. No actual money, but I get the 60% STD for 6 weeks and my position held for 12 weeks. So if your new gig is really family-friendly it could be worth pushing for the 12-week guarantee. It is possible to negotiate your maternity leave on an individual basis; even after you're in the position. Could be worth a try.

As a more direct answer to your question - I wouldn't wait. I'm in the camp that when you're trying, esp if you're having difficulty, the best thing to do in most circumstances is to just keep trying. You never know how long it's going to take and whether you might regret taking time away from it.