Sometimes you just need a BREAK


If you're anything like me, Reader, then at some point in your life (maybe right now!) that desire to shut it all off can be very real.

If you're sitting here wondering, wait, who is this person in my inbox again? My name is Samantha Pillsbury. You may remember me from my coaching business helping high achieving women build more confidence in their personal, professional and dating lives. Well, after over two years of building and running that business, I decided to just stop and take a break.

This might sound glamorous (and on some level it is - I'm so grateful that I had the savings and flexibility to allow myself to truly stop working for a significant chunk of time, because I know that option isn't available to most people) but at a deeper level, it was really friggin' scary.

My whole life I've been an overachiever. The ambitious girl. Classic eldest daughter. The one who left her hometown to "make it in the big city." Even when I stepped away from Corporate America to start my own business, I was still trading one overachieving for another. I pivoted to #girlboss, "in my entrepreneur era," and all the uncertainty and hustle that comes with running your own business.

If I was doing something impressive, I got the compliments from my mom's friends at cocktail parties. My friend's questions at dinner about "how's work going?" were satisfied. My hours were filled with tasks (which conveniently kept the nagging thoughts at bay). Even when the doubt started to get loud enough that I realized I didn't love living in New York anymore and decided to work remotely while traveling Europe this spring, I still was keeping myself so full of stimulation that I didn't have to feel what was going on beneath.

It took being in some bucket list places in Europe and collapsing on the bathroom floor crying because I just wanted to STOP that it hit me that every time something felt off in my life, I just added a new thing to my to do list. Change an offer in my business. Leave New York. Try that new type of therapy. Post more on TikTok.

If the definition of insanity is doing the same thing over and over and expecting different results, I needed to do something different. I needed to stop.

So I flew home from Europe early and headed out to Nantucket for the summer (again, I'm fully aware how lucky I am that this is the place I can just decide to post up for a few months) and when I got to the island, I shut it all down. No work, no posting on social media for my business, no to do lists.

It was like the ambition had left my body. Burnout had set in deep. My logical brain and my emotional brain were at war. And it stayed that way for weeks.

It took until about my fifth week of doing relatively nothing for the fog to start to lift and until about ten weeks for me to really have the desire to do anything again. But by doing very little, I had turned off the drip of external approval and my only source of feedback was how I actually felt. JUST ME! And turns out, the ideas and projects that got me excited were not the ones that I had been chasing.

There is SO much more that came out of this time off but I am not going to monopolize your inbox further today (thank you for reading this far!), so let me conclude this email with the biggest updates from my time off:

  • I'm back to creating content on all things mindset, confidence, dating and money, especially for overachievers and eldest daughters (on Instagram, TikTok, and right here in your inbox) but I'm no longer coaching. You can consider me like an internet big sister, but I'm stepping out of the "expert" role and just sharing what I've learned as best I can!
  • I'm exploring other exciting areas in my career and allowing myself to not have all the answers and can't wait to share more about these changes to give you a real life example of what it looks like to design a career that feels right for me.
  • I'm kicking off my search for a new hometown because living at the beach all summer definitely solidified that leaving NYC was the right decision for me (which means there's lots more updates coming as I'm traveling this fall/spring to test out three new cities and I can't wait to bring you along with me on that adventure).

I hope you'll stay along for the ride, even though things might look a little different around here than they used to. I'm aiming to pop into your inbox a couple times a month with updates, stories and recommendations but we'll see how that timing feels as I get back in the swing of working and creating again. If this is doesn't sound like your speed though, no hard feelings if you decide to unsubscribe.

It's good to chat with you again :)

Samantha

P.S. I am doing a little challenge over on Instagram where I'm implementing a new habit each week of October and Friday kicks off Week 3. So if you're looking for a little accountability, definitely check out the highlight on my profile and you can jump in with me tomorrow!

Diaries of an Eldest Daughter ✨

Join 700+ other eldest daughters, overachievers, people pleasers, and "good girls" to all committed to breaking patterns and building fulfilling lives. Our founder, Samantha is sharing her real life experience as Chief Eldest Daughter in areas including confidence, dating, money and career + answers real questions from the community in "Ask a Big Sister" in this weekly newsletter every Thursday. Come get inspiration, advice and some Big Sister Energy from your internet big sis!

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