Why I’m starting The Jump

A weekly(ish) newsletter for Millennials in the midst of a career transition

The definition of career success has dramatically changed.

In the old world, our parents stayed in the same job for decades. That job gave them financial security so that they could provide food, shelter, and potentially a college education for you and your siblings. Our parents told us to pick a major in STEM or business so we could land a financially secure job. Once you have a jobby job, you’ve “made it.”

To build a successful career in the old world, we plan-and-execute. First, we need to figure out exactly what we want to do. We figure this out through endless self-reflection, introspection, and arbitrary personality tests. Then, we find a job that matches our knowledge of our personality, quirks, and skills. We make a plan to get that job and execute the plan ruthlessly.

As you figured out, the world has changed. Consider these data points:

  • Companies live shorter. The average lifespan of a company listed in the S&P 500 index of leading US companies has decreased by more than 50 years in the last century, from 67 years in the 1920s to just 15 years today.

  • People switch jobs more often. The average person switches jobs about 12 times in their life. The median amount of time a millennial spends at a job is 3.2 years.

  • Freelancing is more prevalent. 20-30% of the working-age population in the US and EU have done freelance work in some capacity. And one in five full-time freelancers earns >$100k/year.

Ask any millennial about what they want to do long-term and you’ll mostly hear this: 

“I don’t know.”


To build a successful career in today’s world, we test-and-learn. We learn about who we are through practice, not theory. We unravel true possibilities by trying new projects, reaching out to people we never thought we’d reach out to, reading about new fields/technologies/trends, and revising our narrative as we tell it to those around us.

Test-and-learn is the backbone of more modern ways of working, such as agile, lean, and design thinking.

Test-and-learn is how organizations succeed in rapidly changing world.

Test-and-learn is how people build fulfilling, wealthy, and joyful careers.

“Sure, you can test and learn. But the foundation of a fulfilling career starts with being clear about the problem you want to solve.”

Here’s the issue: not everyone knows the problem they want to solve. Some do, but most don’t. My friends know me as someone who was clear on what they wanted to do after undergrad (I want to help people harness the new paradigm of work). However, I discovered the problem I wanted to solve through reading, writing, and conversing—all forms of testing and learning.

If you don’t know the problem you want to solve, you identify it by testing out ideas for what you want to solve and learning from your experience.

The Jump

I’m still testing and learning today. 

In June 2016, I packed my bags and moved to NYC to start my dream job at The Ready. After three fulfilling years, I left to explore my next opportunity. I’m currently exploring opportunities from being an internal agile coach, to being a product manager for a company that makes collaboration tools, to being a consultant in the people analytics arm of a multibillion dollar tech company. I’ve taken on four freelance gigs (ranging from editing books about self-managing teams to facilitating a half-day work session for a major consulting firm) and have had more coffee meetups than I can count.

At the onset, I was filled with optimism. I gained a lot of valuable experiences, learned a lot from my colleagues and clients, and was psyched to make The Jump. Now, there are so many things I wish I knew before The Jump. I hear the same thing from my friends when I ask about their journeys: “There’s so much I wish I knew before starting out my career.”

(Side note: arriving at lessons you wish you knew is a sign that you’re testing and learning.)

The purpose of The Jump is to share what I learn with others making The Jump as I navigate my own transition. I’m no expert at career transitions, but I enjoy writing down what I learn and helping people harness the new paradigm of work.

Fair warning, I strongly despise overly simplified advice, so The Jump can veer towards sharing a ton of context and overusing inductive reasoning. Ultimately, I want The Jump to be wide-eyed to the new paradigm of work, yet useful to anyone testing and learning their way toward their next opportunity.

I plan to share a lil something with you every Wednesday morning, right in the middle of your week. And I hope what lands in your inbox is useful, practical, and if anything, thought-provoking.

Are you ready to take The Jump?