Hello ambiguity!

Overcoming self-doubt and designing a fulfilling break

“I did one too and it was the best thing I ever did!”

“I’m so jealous. I wish I could do this as well.”

Those were the most common reactions when I told people I was taking a “career sabbatical”. I was surprised by how many people told me they wanted to take an extended break, and also by how many already had.

4M Americans quit their jobs in April so this is a clear trend (#greatresignation #life-is-too-short economy), and perhaps an easy decision for many. But for me, it was an incredibly hard decision. I’ve agonized over this for years. Even once I decided, it took me several weeks of negating every doubt, fear and excuse before I finally took the plunge. Doubts such as:

What if I don’t get my visa approved when I go back to work? What if the economy tanks and companies don’t want to sponsor H1Bs?

Will I stay relevant in 6-12 months? Will recruiters call me? Can I really get off this treadmill/escalator? What if I can’t find my next big thing and have to ‘settle’?

Friends and family familiar with the visa woes of immigrants asked very reasonable questions like:

Can’t you do these projects during nights and weekends like so many others do? Find your next gig and then take a vacation?

So what helped me overcome these fears?

I searched the web extensively for stories of people who had done this before. Not for stories of the soul searching gap year where you put on a backpack and travel the world to find yourself. Specifically, I sought people like me — immigrant, strivers, product managers.

Designer Stefan Sagmeister has influenced me since my wife introduced me to his work in 2009. He shuts down his New York studio every 7 years to take a year off. In his TED talk, he talks about the benefits of his sabbaticals. I’ve been fascinated by this concept ever since, even though I hadn’t kicked off my career yet.

A slide from Stefan Sagmeister on the impact of his sabbatical

Karan Bajaj is a management consultant turned entrepreneur. He has a 4+1 rule — 4 years of work followed by a year off to travel and write. Time off didn’t pause or reset his career — it accelerated his growth. He attributes this to the depth, dharma and intuition gained on these sabbaticals. Watch his talk to learn more.

I felt that my career would derail completely or flatten. But suddenly when I started doing sabbaticals, I came back and I just accelerated. First time, I thought I was lucky. But I was on an accelerated curve every time I’ve come back from a sabbatical.

This sentiment echoed within my own network. From early-career IC PMs to CEOs, from those dealing with grief to those reaping a financial windfall — extended time off was only additive to people’s personal and professional lives.

And finally, while driving down 101, Jim Collins helped me realize that it wasn’t risk I was uncomfortable with, but ambiguity.

And then it began to dawn on me. They’re taking on increased risk to reduce ambiguity. If you have a job, you know what you’re doing, right? It’s much less ambiguous. It’s the paint-by-numbers approach to life. Going out on your own is a blank canvas. It’s a lot more ambiguous. Where do I start? What colors do I use? What kind of painting do I want to make?

Designing a fulfilling break

What distinguishes a ‘sabbatical’ from a long vacation is intention. Unlike a vacation, sabbaticals typically have a goal or a vector of focus.

Over the years, I’ve accumulated a long list of personal goals, aspirations and new years resolutions that I ‘just didn’t have time for’. My goal is to dabble in all those interests and explore all those what-if scenarios.

To make the most out of this time, I sought wisdom from friends who had done it before. What makes it a fulfilling and joyful experience? Here are 5 pieces of advice that stood out.

Self-love

This is the most selfish gift you can give yourself. Cherish it. Follow your heart for an extended period and just do whatever comes to mind.

It takes 6 weeks to shake off the vestigial remains of your job and truly feel the break taking over. Don’t worry about productivity, job interviewing, etc.

I didn’t quite ‘get’ this before I started but I relate more to this every day. It feels great to let go of any desire for productivity and say ‘yes’ to whatever project or interest I feel like pursuing.

Say ‘yes’ to everything personal, say ‘no’ to everything job related.

Avoid the temptation to interview for roles, no matter how interesting they seem.

I’ve received inbound emails for roles with strong ‘dream job’ characteristics - both intrinsic (mission, impact) and extrinsic (title, prestige). I could feel my stress level rise whenever I started considering what my response should be. Drafting a canned “If you’re still looking in October, I’d love to talk” has been liberating.

How do I avoid the fear of missing out? I remind myself of hedge fund investor Robert F Smith’s epic quote — “Software companies taste like chicken. They’re selling different products, but 80% of what they do is pretty much the same.” That quickly deflates the any notion of missing out on a dream job.

Structure your days and structure your weeks

Across all types of sabbaticals, from travel to family oriented ones, people found it essential to create personal projects and structure their time around these. Without the structure imposed by a typical work schedule, it’s easy for weeks to fly by.

Now that I fully control my calendar, I’ve created a theme for each day of the week and a few categories of time for each day. I don’t follow it religiously (that’s the point), but the guardrails are helpful.

Unique Experiences with Unique people

Try to have unique experiences with people that you would not usually hang out with. You will share experiences with your wife and daughter for the rest of your life. But hang out with the cousin you never see, or a trip with the friend or aunt that may be impossible later.

I thought this was one of the most unique and non-obvious pieces of advice I received.

Don’t worry about the next big thing

Your next thing doesn’t have to be your big thing. After spending such a long time at a place, don’t put a lot of pressure on yourself. Do something that you get some value out of, and use it as a stepping function to whatever the big thing could be.

I originally planned for the top priority of my sabbatical to be ‘take the time to figure out my next big thing’. This advice resonated deeply. It helped me stop worrying and love the process — step back, relax, dabble and explore my curiosity fully.

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A few pictures from week 1 of my time off:

ALL the flavors at Philz Coffee! We talked the manager into doing a coffee tasting for my father-in-law who was leaving for India the next day

Go-karting Grand Prix for Father’s Day with 8 other dads on a Friday afternoon (I finished 2nd, by just 0.2 seconds)

Running into DJ DiDonna at a bar in SF. His article on sabbaticals was the catalyst that pushed me to start exploring it in earnest

Besides those already linked above, here are some useful resources:

• DJ DiDonna: TedX talk and The Sabbatical Project

• Take off your shoes by Ben Feder

• Transitions by William Bridges (I haven’t read this yet, but is widely recommended)

Thanks to my wife Sanyukta for proofreading and editing, and reminding me to use em dashes.