Written by Romi Wallach
When my son was choosing between colleges, I found myself standing at the threshold of an empty home and a new chapter of life I wasn’t quite prepared for. Looking back now, I can see how tightly I was gripping the steering wheel of his life, convinced I knew the exact route he should take. If I could go back and have a heart-to-heart with that anxious, well-meaning Jewish mother, here’s what I would say…
The Illusion of Knowing What’s Best
In those emotionally charged months before my son left home, I had created an elaborate vision of what his college experience should look like. I could see it with perfect clarity: a U.S. college with a vibrant sports culture (not something we grew up with in Canada) and active Greek life. This vision wasn’t just a preference—I believed with absolute certainty that any deviation from this path would be catastrophic for his future.
Now, I look back and recognize those thoughts as the ramblings of someone consumed by fear rather than wisdom. I was so convinced that if he didn’t follow the path I had mentally laid out for him, he would “ruin his life.” What an enormous burden to place on a single decision!
Where My Vision Came From
My idealized college scenario wasn’t random. It was deeply rooted in my own experiences—partly what I had enjoyed during my college years, and partly what I felt I had missed out on. Growing up in Canada, the college experience is quite different. And the dream was for my kids to experience American College life. I was unconsciously trying to ensure my son would have the “perfect” experience that existed only in my imagination.
I failed to see that I was projecting my desires onto his life. I wasn’t seeing him as a separate person with his own dreams, preferences, and path to forge.
The Turning Point: Letting Go
After doing some deep personal work, I came to a profound realization: his path was just that—his. My role as the primary decision-maker for his big life choices had fundamentally changed. Even if I was “right” about certain choices (which is debatable), he needed to learn and grow through his own experiences.
Just because his journey wouldn’t mirror my idealized version didn’t mean he was making a mistake. In fact, his choices might actually lead him to the life he was meant to live—one I couldn’t possibly map out for him.
Finding Peace in Trust
What ultimately brought me peace was learning to trust—trust in him and trust in the foundation we had built together. I had to remind myself that I had raised a son who could think critically, who was kind, compassionate, and an incredible human being. I had done my part.
It was now time for him to make his own decisions and for me to be present as little or as much as he needed. My new role was to help guide him when asked, but not to dictate his choices.
What I Would Do Differently
If I could go back, I would:
-Listen more, talk less. I would ask more questions about what he wanted and truly hear his answers without immediately filtering them through my own preferences.
-Recognize my fears for what they were. Much of my certainty about what was “best” came from anxiety, not wisdom.
-Give myself grace. The transition to an empty nest is emotionally complex, and it’s normal to struggle with letting go.
-Focus on our relationship rather than the specifics of his choices. What matters most isn’t which college he attended, but that we maintained our connection through this transition.
What I Would Keep the Same
Despite my overstepping, there are things I’m glad I did:
-Caring deeply. While I needed to adjust how I expressed it, the love and concern behind my actions came from a good place.
-Being engaged in the process. Even though I needed to step back from controlling it, being present and supportive during this transition was important.
-Eventually doing the inner work to understand my own reactions and find a healthier perspective.
The Wisdom I Found
The most valuable lesson I learned is that our children’s lives are their own. We can guide, support, and love them, but ultimately, they must choose their own adventures. And that’s exactly as it should be.
When I finally released my grip on that imagined future, I discovered something beautiful: watching my son make his own choices and forge his own path brings a joy I never could have anticipated. His life might not look exactly as I once pictured it, but it’s authentically his—and that’s what matters most.
So to my past self and to any parent facing an empty nest: Trust the work you’ve done. Trust the person you’ve raised. And know that whatever choice they make, it’s their choice, their life, and will ultimately help them discover who they’re meant to become.
About the Author
Romi Wallach began working in Financial Services in 2017. In early 2022 she joined NOW CFO as a Business Development Representative in the South Florida market. Romi’s background working with business owners and decision makers has allowed her to expand and provide even more resources and support to the large community of business owners and professionals that she has served over the years. In November of 2023 she became the Director of Business Development for ISA – an organization that provides innovative solutions to business owners looking to grow and scale their business by leveraging remote Global Talent.
In 2021, she co-founded The Daily Drip, a media platform providing content, resources, programming, and community to support South Florida businesswomen on their journey to maximum potential. The Daily Drip is a thought leadership platform amplifying the voices of the modern female business professional. From Palm Beach to South Beach, they are now a community of 4,000 and growing!
Romi serves as a member of the Joe DiMaggio Planned Giving committee, a Board Member for Piper’s Angels Foundation, a 3 x Crossing Crusader in the Crossing for CF, Mentor for the Crossing for CF, Core Committee Member for the Crossing for CF, member of Women Know Y, Club 211 Broward Lifetime member, Circle of Wise Women and Co-President for IBDPros.
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