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Coaching With Jason (v2)

I serve as an executive coach to a small number of founders, leaders, and senior professionals and I consider it one of the greatest privileges of my life.

My typical client engagement falls into one of two varieties:

  • From setback to comeback
  • From burnout to breakthrough

Let me explain.

1. From Setback to Comeback

I coach clients seeking to bounce back from challenging periods of stress, adversity, and struggle and help them use failure and rejection as future for a glorious comeback. Does this sound like you?

  • You're leading a team that just went through a brutal reorg or set of layoffs
  • You're a founder whose product is getting crushed by the competition and you're thinking about pivoting
  • You're a veteran technologist who got screwed by corporate politics and was forced out

I feel your pain. I've been laid off, had doors shut in my face, sued, scammed, been denied promotions, and run entire companies into the ground. But every time, I've dusted myself off and found a way to turn the bitter taste of defeat into a new triumph.

Turning setbacks into comebacks is about learning how to act with resilience, to reflect on the lessons of the past, learn to embrace the struggle of the moment, and act decisively in a new direction. We'll work together to mourn your losses and craft a new path that's all your own, where you define what success looks like and work steadily to get there. Our goal is to get you to that next big win.

2. From Burnout to Breakthrough

I coach clients seeking to find new meaning and purpose after being dragged down by all the crap that school, work, and society through at you. We sometimes get into a rut with our lives and it's not easy to notice it until we're feeling pretty crummy. I liken it to trying to start a fire with wet wood—it's really hard to do alone and a lot better with help! Does this sound like you:

  • You've risen through the ranks in your company / industry but don't feel motivated about reaching the next level and you're not sure why
  • Your business, once a source of pride and fulfillment, feels just like a 9-5 corporate job—tedious and stressful
  • You've become a sought-after expert in your field and you're paid well for your time and knowledge, but it feels like every day is a repeat of the last

I know what it's like to be close to burnout from a corporate job at a big tech company: wall-to-wall meetings, constant sense of pressure and expectations. But I've also felt those feelings of inadequacy and incompentence while doing a startup or an independent venture. I even wrote about pandemic-related burnout for Fast Company.

Going from burnout to breakthrough is all about listening to yourself, clearing off some of your negative thinking patterns and habits, and creating space in your life to explore new opportunities. Our goal is to what's keeping down, find what lights you up and carve out path for a new life. Our goal to get you to a life where you wake up excited for the new day.

Why I Don't Work With Just One "Type" of Person

There are coaches out there who only work with certain types of clients: women, founders, CEO's, engineers, content creators, etc. While I respect that approach, I take a more diverse view on who my clients are. And that's because I've lived a lot of lives and I know that clients grow and change.

As we work together, you may decide this corporate job isn't for you and you want to become an entrepreneur, or that your zombie startup is needs new management and it's time for you to write a book.

Because I've lived many lives, founder, product manager, government tech fellow, freelancer, marketer, I have a special appreciation for how people evolve their interests and skillset as time goes on.

I believe a great coach supports their clients through that journey, focusing on the person, not the title.