And we are winding down on wellness month. It was definitely extended, but that is totally fine because…LIFE. As I was thinking through my apporach and what I wanted to share with you all, I knew that we needed a little Regan Walsh action. Regan is an NYU-certified executive and life coach and all around girlboss who helps others girlbosses who are overprogrammed and underwhelmed to reclaim their lives, both personally and professionally. To put it simply, she’s a God send to many women…giving them permission to shed the shoulds!

I met Reagan through my work with Wardrobe Therapy. Regan is someone who believes in what we do as stylists and is always giving our team the love. And that feeling is definitely mutual, we love her mucho. About a year ago, Regan and I met for breakfast to chat about the influencer world and during that time, I got to learn so much about her. She’s curious, open, confident and wildly encouraging. Since that breakfast date, she’s been a true source of inspiration to me.  There are many instances I find myself thinking, “What would Regan do?” And nine times out of ten, a relevant post from Regan’s Instagram will pop up and speak to my soul.

One of Regan’s mantras that I really resonated with was, “shedding the shoulds.” Whew, those 3 words can preach all by themselves. Until recently, I was the gal who was majorly overcomitted socially and burned out because of it. Talk about tricky. As I began shedding the shoulds, declining events, being honest about what I could and could not do, keeping boundaries, I found much freedom. That FOMO left, because I found happiness in taking control of my life! So good and I owe a lot of that transformation to Regan and the information she so kindly shares with the world.

So for today’s post, here’s some honest insights from Regan Walsh on shedding your shoulds in terms of your social life. Enjoy!

Shed Your Shoulds: How to Avoid the “S” Word in Your Social Life By Regan Walsh

Why are we should-ing all over ourselves?

It’s a question Sex and the City’s Carrie Bradshaw couldn’t help but wonder. After observing herself and her friends battle myriad shoulds (relationships, honeymoons, babies), she mused, “I wondered if should was another disease plaguing women.”

She’s certainly not alone.

Commonly called the “s” word, “should” has become something of a profanity in the age of self-care and self-awareness. And yet, we still use it. A lot.

Our social lives in particular seem to be a breeding ground for shoulds. After all, it’s hard to make friends when you’re an adult, and we often feel obligated to say yes to everything. So here are three social shoulds and how you can set boundaries to shed them.

No. 1: “Let’s have coffee!”

 You get the text from an old colleague or a DM from an Instagram friend.

Coffee dates with each and every casual acquaintance can quickly become a distraction in an already jam-packed schedule. If you feel guilty about simply saying no, try suggesting a solution that feels better to you, like a co-play date with your kiddos.

As a career and life coach, I get these texts frequently, and I used to say yes to them all. We’d meet, and they’d chat about their current professional and personal obstacles. I’d offer advice, and they’d leave feeling energized. But I often felt cheated out of time with paying clients, so I set a boundary of kindly turning these down.

Recently, a former client asked me to lunch. I said no, but I recommended we take our kids for a walk in the park together instead.

“I like how you say what you will and won’t do,” she wrote back. “I need to work on that.”

  No. 2: Rubber Chicken Dinners

Philanthropy and nonprofit involvement can be incredibly rewarding, but it inevitably comes with a lot of invites for what I like to call Rubber Chicken Dinners.

It’s easy to feel the pressure of being seen at these types of events, especially if you’re hoping to expand your professional network. But if you dread them, politely decline—and consider alternative ways to make more meaningful connections.

Write a handwritten note to the colleague you would’ve likely seen for just five minutes at a luncheon. Or find a way to volunteer with an organization of your choosing, perhaps with a few of your friends or coworkers.

I recently declined an invite to my favorite nonprofit’s largest annual fundraiser with the intention of making an in-person visit so I can witness their mission in action. That way, I can stay connected in a way that feels authentic to me—no rubber chicken necessary.

No. 3: Brides and Babies

Much of our 20s and 30s could easily be spent on the bridal and baby shower circuit. The thing is, we tend to not enjoy them. Nothing says obligation like a gathering of people who barely know each other and are required to play games and make small talk while one person opens gifts.

If you don’t love showers, just RSVP no. Then find a more personal way to say “Congrats,” like dropping off a gift in person or sending a handwritten note with an invitation to lunch. It’s important to celebrate the big moments in the lives of our friends and family, but we can certainly decide ourselves how best to do that.

Ultimately, if the shoulds are plaguing your social life, listen to your gut, set boundaries and bow out honestly and gracefully.

What happens when we stop should-ing all over ourselves? Happiness.

Say no to shoulds so you can say yes to joy.


Regan Walsh is an NYU-certified executive and life coach who focuses on helping women who are overprogrammed and underwhelmed to reclaim their lives, both personally and professionally. She contributes to Harvard Business Review and Forbes, and has been featured in Fast Company,, Today, and Real Simple.
She has coached thousands of women through her one-on-one and group coaching programs, and she is regularly asked to give keynotes, facilitate workshops, and speak on panels for Fortune 500 companies, industry associations, and foundations. She has done so for clients like Nike, QuickBooks, and JPMorgan.
Regan is located in Columbus, Ohio, and coaches people from all over the world.


There is this unique relationship between confidence + dress. They truly compliment one another and as a direct result, one strengthens the other. As a society, we are learning that wellness is so much more than just exercise, but a true lifestyle. Your thought process, how you are fueling your mind, how you are caring for yourself, what you are projecting to the world. It’s truly a holistic concept. One of the things we have been developing at Wardorbe Therapy is offering our individual personal styling experiences on a corporate level, as part of the wellness opportunity these businesses can offer their employees. There are 3 different levels of services we can provide and would love to share more with those of you who might be interested. Feel free to shoot an email to for additional insights. I feel strongly that the power of dress is a part of the holistic wellness mindset, which is what I wanted to share. For the month of May, if all goes back to normal, I will be doing a big spotlight on PERSONAL STYLE. So stay tuned. Lots of good stuff to come.

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