My Dream Job Ended Up Making Me Miserable — Here’s How I Coped

While the romance of landing a dream job can transpire with an exciting rush, if we don’t consider the nature of challenges objectively as they come up, they can easily become obstacles that lead to major suffering. We’re often too emotionally invested in our dream job: a sense of identity and identification with achievement. We believe our dream job is who we are. It’s hard to let go of a hard-won, long-dreamed of and ideal identity.

If our dream job turns into a nightmare, we think there’s something wrong with us, our abilities and our value. I know, because I’ve been there. A few years ago, as a young entrepreneur, I landed my “dream job” in a new industry with one of the first companies in the space. I was employee number one, and helped take the company from three  founders to a venture-backed firm of 40 people in two years. 

With carte blanche, budget zero and a tank full of ideas, I rode the wave of startup life. I was a pioneer, marketing executive, founder and leader. It was more than a dream job — it was my identity. 

My wave crashed when a team of older, "experienced" men (from the industry we were disrupting) was hired to run the company. Needless to say, there was a culture clash. Tension grew with new management, but I was fiercely attached to my dream job and career-identity; I was in denial and too proud to see the truth. Though I wanted to ‘stay for the team’ and be strong for others, I neglected myself. Emotional distress and anxiety led to depression and burn out just six months later. My dream job was making me miserable and I didn’t know what to do. I hit rock-bottom.

Initially, I “dealt” with the situation in less-than-optimal ways: 

1. I developed defensive tunnel-vision, seeing myself as a target and a victim. My pride and ego got in the way; I was focused on proving myself and defending my way of doing things. 

2. I went into mental overdrive: overthinking, overanalyzing and getting nowhere. I lost confidence in my abilities. My outlook became critical and negative as my self-esteem took a nose-dive.

3. I stopped exercising, socializing and doing things I enjoyed. Personal relationships suffered as I became cut-off, and emotionally unavailable. I felt alone and miserable, but I was too afraid to talk to anyone about it.

I didn’t realize it at the time, but it was all happening unconsciously. Back then, if you told me I was in denial or trying to save a sinking ship, I probably would have snapped at you. Emotional outbursts and ‘losing it’ over small things are clear signals that your unhappiness is running deep. 

It took objective and honest self-reflection to gain the perspective I needed to see things clearly — both at work and in myself — so I could take empowered action. How did I do that?

1. I had a talk with my ego. 

What was I so attached to? The role, the prestige, my reputation, my past successes? Or, what people thought of me? How important were these things, really? Did the external validation, labels and caché matter that much? 

2. I had a talk with my soul. 

Was my sense of self really this job? What was truly important to me? What were my values, dreams, aspirations and passions? What were my intentions for my career? What was my big WHY? 

3. I talked with key people. 

I opened up emotionally, asked for objective advice and constructive feedback from mentors, family and friends. I let myself be seen and supported. It felt good to know I wasn’t alone.

4. I flipped the mental script.

 I made a conscious effort to change my negative mindset (no more blaming or victim mentality) to a constructive mindset (seeing the lessons and opportunities for growth). I took responsibility and accountability for myself, while being grateful for everything in my life.

5. I accepted and let go. 

Life changes, people change and jobs change. I evaluated things realistically and objectively. I let go of my identity, ego-driven preferences, expectations and disappointments, and I welcomed new possibilities with confidence and inner strength.

The most important question I asked: how could I actualize myself and find alignment to my dreams and desires? 

Sometimes, truth leads to reconciliation and sometimes it leads to an ending. It always leads to clarity. When one door closes, we can choose to open another one. Trusting in myself, I negotiated an amicable exit with the company and moved into the next exciting chapter of my career. 

This experience taught me about attachment, mindset and letting go. It taught me to evaluate a job not as an identity, but as a choice to align a role with my values, aspirations and passions. 

I am not my job. You are not your job.Knowing our values, motivations and goals is vital to understanding whether a job is conducive to our dreams. 

With self-awareness we make better decisions in every moment, especially the most challenging ones. That self-awareness will be needed when you’re attached to a dream job.

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