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The 3 big “Wish I would Have Knowns” all working moms need to know

By Janet Winkler

On our journey to create Hacking Sophia, a digital platform designed to deliver career and life wisdom and solutions to time-starved working moms, we heard dozens of “I Wish I Would Have Knowns” from the more than 150 in-depth interviews we conducted with working moms. 

Things like: “I wish I would have known that despite all the little screw-ups, all the moments of self-doubt, all the times I asked myself if I was doing the right thing, my kids were going to turn out ok, because they did.”

This lesson, like all the rest, was unfortunately learned in hindsight. 

I too wish I had known them. There were too many nights that I laid in bed, after keeping it together for my kids, admitting to my husband “I don’t think I can do this anymore.” I had founded my own business, grown it to a company that serviced global clients with a best-in-industry reputation, worked with an incredible group of inspiring, committed, brilliant women and men — and I also had 3 children, a husband, and in time, a dog. I often felt like I was busting at the seams.

I knew all too well the challenge of being a working mom and navigating two competing time-consuming worlds — work and family. For my next chapter, I was determined to help all women, but with an emphasis on working moms living in, what we call, the Cram it all in Years, the years where career acceleration and babies and young children collide. 

Out of all the “I Wish I Would Have Knowns” that inspired the wisdom we share with the Hacking Sophia community, three big jewels emerged consistently as the foundations to prioritize, to help the shift from ‘post-baby just hanging on’ to living life more fully. Most of our Sophia Contributors learned these through challenges, often (also) experiencing a “can’t do this anymore” moment and wishing they would have known and acted on these pieces of wisdom earlier. Personally, I really wish I would have known and acted on these three early on. I know I would have saved myself a lot of hardship. 

1) Define Your What Matters (and you’re ‘not so much anymore’).

“It took me until my second child to really think through what mattered most to me. It was my immediate family, my career and my well-being. Full stop. The rest of the shit I was doing, that I thought was really important or gave me joy, just couldn’t fit anymore.” — A Sophia Contributor

Early on, everything that used to matter is still there plus add in a baby, then maybe children, and things quickly get overwhelming. Deciding what you really care about as it relates to baby/children/family, life and work in your new reality is essential. If how you spend your time doesn’t align with the core of what you really care about, your world is out of sync and you’re left feeling frustrated and certainly exhausted. Here’s how:

  • Define the big categories of things that matter most to you. Think about where you want to spend your energy, and in the Cram it all in Years think in shorter windows, like a 6-month horizon. Categories could include: immediate family, career, self-care, social time, creative outlets, etc. Just jot them down.
  • Distill your big categories of “what matters most now” list down to a top 5 and identify and define what doesn’t matter so much to you anymore. Choose your top 5, and by default, deprioritize what is less important to you. It can help to assign a value, a simple 1 – 10, to force choice.
  • List your Supposed To’s: Get these off your chest, your mind, your conscience! We’re overloaded with “I’m supposed to’s” whether it’s from social media, assumptions about what others think you should be or do, or other expectations that you accumulate. List your supposed to’s so you make the invisible visible, eliminate what doesn’t serve you and hold onto what’s important to you. Examples include: being my extended family’s ‘go to’ for advice, serving homecooked meals to my family, returning to my pre-baby fitness level, and more.
  • Write your clarity statements: For your top 5 categories, assisted by your list of ‘supposed to’s,’ add in your “why” these matter as a reinforcement and a check that you’re prioritizing for the right reasons (for you, for your family) and what you want to achieve (how). Here are some examples:

(What) Spending time with my immediate family is important to me (why) because one of my greatest joys comes from being a mom (how) so I’m going to make sure I invest quality time with them when I can be most present.

(What) Advancing career is a priority for me (why) because I enjoy the stimulation that comes from applying my skills and I want to continue to advance upwards (how) so I’m going to make sure I focus on what is going to drive my career forward, minimizing ‘other distractions” while I’m working. 

“There were too many nights that I laid in bed, after keeping it together for my kids, admitting to my husband “I don’t think I can do this anymore.” … I often felt like I was busting at the seams.”

2) Fierce Prioritization and Ruthless Boundaries.

You’ve done the hard part — the choices around how you spend your time and energy. Turn these “top 5 matters” into activities and actions, assigning time and get them in your calendar. This is what you fiercely protect and communicate to others, unapologetically. Continuing with the above two examples:

Immediate Family:

  • Spend quality time with my family: 
    • Be home by 6:30 pm 3 nights a week to bath and put my baby/kids to bed. 
    • Be fully present with them during that time; no emails, texts during that time.
    • And, relax my ‘supposed to’s’ around homecooked meals.


  • Advance my career:  
    • Ruthless focus on career advancing priorities by defining the 3 business critical priorities that will demonstrate success in my role. 
    • Defining the associated action steps to make that happen, the resources/support required, determining what to delegate and what to eliminate that doesn’t fit.

3) Assemble Your Team (Personal & Professional)

I wish I had leaned on my tribe more. You need an outlet of realness. You need a friend who you can call and say anything to without judgement. — A Sophia Contributor

We can’t and shouldn’t do it alone. Action it. Start by choosing which people are most critical to you and give yourself time to find them. It’s not a race!

Here are some examples that emerged as the early important ones:

Life: Childcare Team, 911 Friends, Trusted Advisors, Moms who have your back,
Work: Got Your Back Peers, Advocates, Mentors, Investors

Remember, as you consider the above, perfection is the enemy of done! Get started so you make choices. 

While I wish I would have known that despite the many screw-ups and agonizing periods of self-doubt of whether I was a good mom and business leader, I’m happy to report that I have three amazing adult children, each accomplished in their careers, each in healthy relationships, the same loving husband and a career that I can honestly say, “Wow, I got to do that!”

Janet Winkler

Janet Winkler

Janet is an experienced leader, entrepreneur and marketing specialist. Janet founded in-sync, an insights-based brand consultancy which was acquired by Publicis Groupe where she was appointed Group President, Publicis Health. Following her retirement from Publicis, Janet became a Senior Advisor at McKinsey & Company. However, Hacking Sophia was calling. It was born out of a desire to help working moms thrive in personal and professional lives.