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Family Friendly Career Tips

Compiled and edited by Julie Tereshchuk

Dear Mentors,

I am getting married later this year. As I think about the impact on my career of starting a family, do you have any tips? Should I start to think now about finding a position with a company that has good maternity leave, childcare options and flexible work hours? Or am I searching for a corporate unicorn and should consider going independent as a freelancer?


Hoping To Be Three


Dear Hoping To Be Three,

Consider pursuing 100% remote work with benefits, if this type of culture is preferable to you. As backup, seek an onsite culture that values and actively supports families. Do so by requesting informational interviews of individuals that work at your ideal company. Having freelance assignments as an option is a viable solution, however, the stress of the ups and downs of generating income may pose to be far more than you want with a new baby in tow.

Also, you may find this New York Times article a useful resource.


Christine Moline


Dear Hoping To Be Three,

A quick caveat: I don’t have any little ones so am not speaking from experience, just my own perspective.

If you are at all thinking of being a working parent, absolutely I would look for a company that has policies and a culture that are supportive of working parents. Many companies nowadays have realized the value in providing generous leave (even paid leave!), flexible hours, and sometimes even on-site or reduced-cost childcare. Since it sounds like you’re planning pretty far ahead, you have time to be choosy about your next step. Best of luck, and congratulations!


Gina Helfrich


Dear Hoping To Be Three,


Babies come with a lot of surprises and there is no simple answer to your question. Of course, flexibility will be welcome over the next 18 years. But, getting married, starting a family and changing jobs may be more than you want to tackle at once. Some considerations…

If you are new to freelance, make sure you have a clear idea about how much time will be devoted to the paperwork of starting and running a business, not to mention drumming up clients! All in addition to the work you plan to offer.

On the other hand, you may want to weigh the benefits of paid sick time, health insurance, professional training and the relative security that a corporate job can provide. Have you explored whether your current employer will accommodate a switch to part-time or work-from-home?

Of course another surprise with babies is that they don’t always arrive when and how you expect them. I know many couples who ended up waiting years, not months, for that bundle of joy. So, as with everything baby-related, make good plans, but be ready to adjust!

Best of luck to you.

Sandra Kleinsasser


Dear Hoping To Be Three,

I strongly encourage you to tip your toe and the water and see what kinds of benefits are available for new parents at companies where you might be interested in working. In times of high employment, benefits become more competitive. There are options! If you don’t find a job you want with attractive benefits, you can always work for yourself and, I hope, get on your partner’s health plan.

Good luck!

Mary Ann Roser


Dear Hoping To Be Three,

The career-building you do in the right company will be foundational if and when you decide to freelance.


Karen Aroian