Lukewarm Coffee and Major Mistakes: My Sensitive Striving Story

One summer Saturday night, sitting at a half-empty Starbucks in NYC, I realized how much my addiction to achievement had taken from my life.

That evening was rare in New York City—it was the perfect weather to walk in Central Park or have drinks on a rooftop with friends.

Instead of having fun, I was sitting by myself nursing a lukewarm latte and realizing that I had made a terrible mistake.

I had just bailed last minute on a close friend’s wedding weekend. My hotel was paid for, travel arrangements were made, and I was excited to see all of my friends from college in one place.

But the anticipation was always accompanied by guilt. I couldn’t shake the constant reminders from my inner critic:

“You have work to do. Who do you think you are taking an entire weekend off? What about your career? Everyone is going to think you’re lazy.”

At the time I was working in a high-pressure job as a researcher. When I wasn’t running around frantically trying to accomplish everything on my never-ending to-do list, I was squished between Wall Street bankers on a bus heading into or out of New York City at rush hour, with a two-hour commute ahead. Every day, I’d wake up at dawn and go non-stop until I fell asleep with my computer on the bed. Then I’d do it all again the next day. 

From the outside, it looked like I had it all. I’d followed society’s recipe for success. I was highly accomplished, landed a great job in the city, and was on a stable and steady career path. I’d entered this career thinking I was doing what I was supposed to do. I’d always been diligent and responsible; I made good grades, graduated at the top of my college class, and got a job that, from all appearances, would deem me successful.

But on the inside, I was a mess. I was frazzled, restless, and emotionally depleted. I’d done everything I was supposed to do… but all I’d really done was build a life that didn’t feel like mine.

Rather than seeing my emotional state for what it was—a sign that I was living an unsustainable lifestyle—I internalized my sadness and frustration. I assumed I wasn’t good enough for the job. I had tried so hard and had done everything “right,” and yet I still wasn’t happy. Perhaps I was simply a failure.

This lack of confidence is common in Sensitive Strivers who are so attuned to what is going on both within and around them that it is difficult, if not impossible, to focus on their own well-being and personal goals.

They’re worried about what others think and so influenced by society’s definition of success that they don’t know how to direct their energy toward what they really want—an accomplished life coupled with a sense of inner confidence and control.

They’ve been taught that “success” means having a lucrative job that’s approved of by parents and peers, and climbing to the top of a career ladder. If, even after attaining this so-called “success,” they still feel unfulfilled or like they’re struggling to keep up with the pressure to do even more, they assume the problem lies with them–they’re too sensitive; they need to suck it up or work harder—instead of considering that, perhaps, their emotions are telling them they need to approach their career (and their relationship with themselves) in a new way.

In my case, instead of listening to my intuition saying something was off, I ignored it. I worked harder and longer to compensate for my insecurity until the stress broke me. I spent weekends in bed because I was too drained to do anything else. I had heart palpitations and nightmares. I felt like a shell of a person. The thoughtful, compassionate self I knew was MIA.

Just three years into working a job I thought I’d have until I retired, I quit out of necessity.

When my health forced me to step back, I realized that the problem wasn’t that I was failing at my job. The problem was that I had allowed other people’s expectations to consume me. I was doing work I felt I should be doing without ever pausing to consider if it was bringing me closer to my goals.

That realization helped me transform my burnout into a new beginning and open my career coaching practice. I knew other women were struggling similarly, and I wanted to help. At first, I didn’t have a name for this group of women, but after hearing their stories and learning how they operate, I realized that their challenges go beyond what traditional career advice offers and requires an understanding of their built-in sensitivities. My coaching work still took a tremendous amount of time, energy, and focus, just like my previous job. But coaching fulfilled me in a way my previous career hadn’t and allowed me to build the life I wanted.

Yes, removing myself from an intense work environment was a boon to my wellbeing, but it also helped me craft a career aligned with my values – one based on independence, flexibility, and helping others. For years I had followed what society defined as a “good job” and the picture of success, all the while ignoring my intuition, which kept telling me something was “off.” Coaching gave me the opportunity to use my creative strengths and passion in new and productive ways.

As my confidence grew, so did my business. My inclination for discipline, dedication, and hard work perfectly positioned me to lead clients through their own journeys. Now, I can channel my sensitivity in a way that satisfies me and also moves my clients forward. Starting my business allowed me to see I could trust myself to do what was right for me versus what others expected.

Let me be clear… I’m not advocating that you leave your job as I did. Changing careers is what felt right for me personally. Truth be told, every day isn’t perfect. In fact, entrepreneurship has presented new challenges to managing my ambition and sensitivity (comparing myself to other business owners and managing my tendency to overwork, to name a few).

But I am advocating that you step back to consider whether the ladder to success that you’re climbing is leaned against the right wall and if your habits are sustainable.

So today I want to encourage you to take stock to examine your own behavior, expectations, and definition of success.

Ask yourself:

  • Is how I spend my time a reflection of my values and the life I want to create? 
  • By what (or whom’s) metrics am I measuring my success by?
  • How will I tell when I’ve “made” it or feel like I’m done enough?

The answers may surprise and enlighten you.

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