A Type-A Guide to Time Off

mollie chen
4 min readSep 1, 2016

This past June, I left the company I helped start and helped grow over six years, from pre-launch to a million plus customers. Rather than dive right into something new, I knew I needed a break, but I didn’t know what that meant — I’d never had mid-career time off before, and there was no helpful roadmap. (Seriously, one of the first Google results is, “Why Your Free Time is Boring.”)

To complicate matters, I’m pretty terrible at relaxing. I can’t sit still, and am constantly thinking of how to get more done. My idea of a lazy Sunday is a workout, farmer’s market trip, and avocado toast before 10. Given my history of ants-in-pants-ness, I knew it’d be a challenge to make the most of my mini sabbatical, and that I could easy get uncomfortable with the lack of momentum.

While I’ve read plenty of smart pieces about how to get, keep, or quit jobs, there’s surprisingly little about what to do with the in-between periods. As someone who just went through it and has probably spent too much time thinking about this, I’d like to share what I’ve learned.

Transitions are Hard (And You Can’t Predict What Type of Hard)

In the weeks before and after I left, very smart people told me the transition would be tough. I believed them, but didn’t know what flavor my hard would take. Turns out, the same emotion and energy I threw into my job could easily be transposed into anxiety about how to spend my newly unlocked free time. Where I’d previously puzzled over org design questions, I now puzzled over proper optimization of summer days; where I’d once stressed about marketing program ROI, I now stressed over whether I was relaxed enough. I wasn’t relaxed, if you were wondering.

Ask for Advice (But Only Take What You Need)

What I found very quickly is that everyone has advice about how to use time off. Some friends jealously suggested I buy a ticket and just go. Anywhere. Others told me to sign up for a month-long coding/photography/cooking course. The best advice came from those who had also been through a self-imposed and extended transition themselves, and was blessedly simple. Buy a notebook. Write down your feelings, ideally in the morning before you have a chance to pick them apart and judge them. Make personal goals, not professional ones so you can feel a sense of accomplishment. Even though you’re a nice person, it’s okay to say no to coffee meetings or “pick your brain” requests for a set amount of time. Give yourself a break. Eat ice cream.

Add Structure and Goals (But Not Too Many)

I spent a lot of time thinking about what I wanted to get out of my time off, besides a full eight hours a night. I made lists : how I wanted to feel, things I wanted to do, topics I wanted to explore. Setting goals for time off might sound counterintuitive but I found it was the only way for me to combat the incessant, “Is this the best way to spend my time?”

And it helped that many of my goals were fun. I needed to reset my brain, and remind it how to think outside of my all consuming six-year long job, so I weaned myself off my devices (though let’s be realistic, Snapchat and Instagram not included). I stopped reflexively checking email, and for the first time left my laptop unopened for days on end. I read the news instead of skimming it, and got deep into podcasts.

I also wanted to spend time on areas of my personal life that had been neglected because of 80-hour work weeks. I finally got through the pile of un-dealt-with mail on our dining room table, and Marie Kondo-ed my closet. I challenged myself to 30 days of yoga, Citibiked instead of Uber-ed, explored volunteering opportunities. I learned to garden, and now start my day by watering my tomato plants and checking my kale for marauding cabbage worms (terrors, I tell you).

Finally, I forced myself to slow down, to turn down the stream of coffee invites that came in once the news spread and spend long afternoons on my own. I said yes to things I might not have made time for otherwise: a week-long yoga retreat, a summer camp themed work-life conference, a last-minute trip with my best friend and my sister.

In Summary

If this sounds like a lot of navel-gazing over two months of vacation, perhaps it is. But it’s an incredible luxury to be able to take time off (financially and otherwise), and I don’t know when I’ll have the opportunity again. Now, as I shift into job-searching mode, I’m doing so from a place of confidence in what I want, rather than reflexively jumping into something just to fill the void.

So, for anyone who is thinking about, or going through a transition, my advice is simple. Know it’s going to be both scary and exciting. Listen to the smart people in your life, but follow your instincts. Set goals, but not too many. And then give yourself a break. You’ve earned it.

Next Chapter: How to Find the Job After Your Dream Job.



mollie chen

vp of brand and customer experience at hungryroot. birchbox cofounder.