When Success Isn’t Enough

With the right habits, productivity techniques, and focus, anything is possible! At least, that is the message we hear. But this message is missing a key piece. I found out the hard way. 

Since high school, I pushed myself to constantly improve. I read all I could about life, productivity, and leadership. Over several years, I built a consistent routine and fast-tracked my career in hospitality. I loved my job and even the most difficult guest didn’t scare me. I read one book a week and was writing a book about productivity. I did push-ups between focused writing sessions and went for a run every morning. I went hiking, journaled and drank tea. Even something as mundane as brushing my teeth was optimized by doing calf raises at the same time. Everything I did was focused on being the best I could be.  

When I was 24, a good friend of mine became the General Manager of an iconic hotel. I was thrilled when he asked me to apply as the Assistant General Manager. After several interviews with various levels of leadership, I got my dream job and the opportunity to work closely with a dear friend. The jump from a mid-level duty manager to a senior leader of an entire hotel was daunting. But I was sure my habits and checklists would help me excel as a leader. 

But life quickly fell apart. Instead of running every morning, I rolled out of bed, thankful I’m blond and could skip shaving for a day or two before it became noticeable. Instead of leading with humor and intention, I demanded perfection from my team and was critical of any failures. Instead of responding to guest complaints with empathy as I used to, I was snarky and cold. At night, I was crushed by anxiety about everything I had messed up, missed, or could have done better. 

No matter what I did, it never felt like enough. Maybe I felt underqualified because I was; I just needed to work harder to keep up. Maybe the reason I couldn’t focus was that I had gotten lazy; I just needed to double down and stick to my routines. Maybe I responded to my team poorly because I was a mean person and the power was going to my head; I just needed to try harder to be nice. So I tried harder, worked longer, and used every ounce of motivation and all my years of research to improve. But things got worse. 

By the end of summer, I had worked 16-hour days for most of the last five months and was sleeping in the hotel, answering phone calls and checking guests in overnight. Even though our guest satisfaction scores were 50% higher than the corporate goal, I felt like we were failing. I wasn’t journaling, I barely ran, and my mind buzzed constantly with ideas and tasks. At night, I often had panic attacks and worried about losing my friends and my job.

I felt like a lousy leader, a failing friend and a fraud in every area of life. I was doing everything I could, but it wasn’t enough. What was I missing? 

~ ~ ~

This question consumed me. After we closed the hotel for the season, I worked to identify what I had missed. 

On a two-week road trip, I thought of little else. I took a notebook and audio recorder on all of my hikes and made hundreds of observations and theories about why I had fallen apart. Did my routines fail me, or did I fail them? The hotel did well, so why did I feel like I had failed? Why did I feel like such a fraud? Everyone I talked with became a sounding board for my ideas (even a random guy I met on the bus). I was obsessed with finding the answers.

I read books, searched articles and listened to podcasts on everything from stoicism and productivity, to emotional intelligence and attachment theory. I scoured my mental catalog of research for anything helpful. 

Finally, a podcast between Brene Brown (a researcher on leadership and emotions) and James Clear (an expert on habits and entrepreneurship) combined the worlds of productivity and emotions and gave me the missing piece. 

They asked, “What is the unfulfilled need behind your desire to work so hard?”. I started to wonder whether the problem lay with my habits and routines, or with me… how I viewed myself and where I found my worth. I didn’t want to think about this; it was so painful.  

My unfulfilled needs were approval, acceptance and self-worth. All these years I had been working to be perfect. But no checklist or routine would make me feel like enough. This job was so big, with so much to learn, it was impossible to be perfect. I felt underqualified because the job was tough, so I worked harder. Because I worked harder, I stopped enjoying running and reading. Because I stopped enjoying life, I was tense. Because I was tense, I was critical of my team. Because I was critical of my team, I felt even worse as a leader and worked even harder. It all came to basing my self-worth on performance. Finally, I knew what I was missing. 

~ ~ ~

Identifying the missing piece was just the first part of the journey. Once I understood what caused my breakdown, I had to work to change my mindset. James Clear says “Every action you take is a vote for the person you wish to become.” Instead of getting worth from my perfect routines, I’ve used all my research and routines to help me build confidence in my self-worth. 

I want to feel good about who I am as a leader and become a great leader. So I’ve let the showy, performative work slide and now sort my schedule into “busy work” vs. “deep work”. Each time I take time to coach my team well, and each time I make a joke and a guest laughs, it’s making a vote to be the leader I want to be. 

I am running again. But this time, it’s not to maintain a perfect streak on Strava or earn approval. I run because it clears my mind and helps me stay balanced and healthy. Each time I run, it’s a vote for who I am.

Understanding who I am has also been a large part of becoming who I want to be. I have been going to counselling for several months to try to understand what I actually place value on and where I’ve learned to think like this. I’ve also been making a practice of journaling. Every day, I write out one thing I’m proud of and one thing I’m grateful for. These actions are votes to understand and affirm the best parts of myself.

I’m often unsure if I’m on the right path. Society seems focused on productivity. My own quick success shows just how powerful habits, productivity psychology, and focus can be in helping us achieve our goals. It’s risky to try something new. Habits and productivity should not be a goal unto themselves. They are designed to help us achieve our goals and become the people we want to be. My experience shows that no habit or checklist will ever be able to make us feel like enough. Something will always be missing. 

 Our value can’t come from achieving or chasing perfection. Something will always make us feel like we’re not enough. Poor self-worth will hijack our best intentions and ruin our happiness and connection. To engage with the world and others in a healthy way, we must have more than a solid routine, we must have a solid self-worth. Our self-worth is built the same way a routine or habit is built. One choice, one vote at a time.