My wife is just starting a new job that has a very good 401K plan. What I'm wondering, though, is if it makes sense to contribute from day 1 or wait at least a little while to see if the job is working out okay. It is something totally new for her and for all we know, she may not care for it once she is actually doing it. She will only be working on a per diem basis so there won't be a great deal of money involved. I'm just thinking that it might be more hassle than it is worth to contribute for a month or two and then have to transfer the money if she leaves the position. On the other hand, I hate to give up the 50% match if she ends up staying (needs to be there 2 years to be vested in the match).
What would you all do? Contribute from day 1 and hope for the best or give it a month or so.
What would you all do? Contribute from day 1 and hope for the best or give it a month or so.

50% match is something you wouldn't wanna miss on account of a "whoops, we thought..." scenario. I would suggest always contributing from day one. Some companies may even have a limited enrollment period for new hires, and you may end up waiting a long time to catch the next period ('tis what happened to my husband).
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