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When my sister died, I focused on improving my work life. It helped me stay present and deal with my grief.

Jason Silver   

When my sister died, I focused on improving my work life. It helped me stay present and deal with my grief.
  • When my sister died of cancer, I struggled with my grief.
  • I turned to wellness hacks like cold plunges to try and move past the loss, but that didn't help.

I'm standing in the corner of the only unoccupied room in Sunnybrook Hospital's emergency center in Toronto, making a phone call. I'm about to say the hardest sentences of my life.

My dad picks up the line. I pause. I don't want my voice to crack, but it does, anyway. "Well, Dad, I have some hard news..."

Our call ends, and the weight of the day crashes down on me. I'm physically sick, but I make it to the bathroom before causing another issue for the busy medical staff to deal with.

I was calling to break the news to my parents that my sister, Rachel, had late-stage cancer, and they needed to get home fast. Less than a year later, Rachel lost her battle with cancer.

I struggled with the loss of my sister

I knew I wasn't coping well with my sister's death. And so, when a high-achieving friend pitched the idea of meditation, I listened. When a second and third friend brought up meditation, I gave it a go. I felt better. I felt in control.

Next came therapy and then reading. From here, I went full Tim Ferriss. I spent every free moment reading books on self-improvement. I tried several personal wellness experiments, such as intermittent fasting, polyphasic sleeping, and cold plunges. For months, I'd start my day in freezing cold water, often opting for a dip in a lake on the brink of a frigid Canadian winter.

At the beginning of my cycle of experimentation, I noticed leaps and bounds in the improvement of my mental health. But then it plateaued, and I had diminishing returns.

I realized that all of these experiments had a limit because I was ignoring my job. Back then, I was your typical Type-A, borderline workaholic (OK, total workaholic). I had founded multiple companies, been a relatively early employee at Airbnb, and was in the middle of building an AI company. I worked hard and told myself I'd be happy once I'd "made it."

When I stepped back, I realized I was over-invested in the future and under-invested in the moment.

I turned my grief toward work

To focus on the here and now, I applied a similar experimentation approach to my job. Instead of a therapist, I got a coach. I began meditating on the job and read dozens of workplace improvement books. I paid attention to my energy levels at work and how I approached tasks. I questioned everything that I thought I knew about productivity.

In my cycle of wellness experimenting, adding activities led to the most improvement. At work, it was the opposite. I always assumed that doing better at work meant adding a better project, a bigger promotion, or a brilliant new job entirely. In contrast, tactics that removed frustrations from the job improved my well-being at work the most.

For example, once I started paying attention to miscommunications, I noticed that I would regularly lose 15 minutes on Monday or half an hour on Tuesday. It turns out the average employee loses a full day of productivity every week due to miscommunications. That meant I could accomplish five days of work in four if I could stop miscommunications.

I spent weeks looking for a solution and found a simple one used by soldiers that works by repeating back your understanding. It's called a brief back, and all I had to do was take a tactic meant for the battlefield and adapt it to the boardroom.

Brief backs take less than 30 seconds and often save me weeks of wasted effort. Rather than assume alignment, I confirm it before a miscommunication occurs.

Focusing on the day-to-day problems at work helped me stay present in my life — better than any of my personal wellness experiments. I finally felt I had control again. Ultimately, it helped me heal the loss of my sister.

The experiments returned a sense of agency to me

What began as a search for anything that could help me cope with losing Rachel turned into a borderline obsession with emotion and wellness. I couldn't control that I lost Rachel to cancer, but I could control how I responded to the grief of losing her.

Although I plateaued with the life hacks, tweaking how I work day-to-day has led to endless gains. I still work hard, but now I work better. I feel better, too — and not just at work. The better I do at my job, the more joy I feel in my life overall. I'm less stressed, more driven, and more productive now than ever.

I'd trade everything I've learned to bring Rachel back if I could, but I can't. So, instead, I'm on a mission to share these lessons so you can have my gains without my grief.



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