Hiya friends!
Writing to you this week from NYC, where the city is exploding with fun summer activities, but it has also been 40+ degrees (that’s celsius, I will never accept another form of measurement), and incredibly humid and swampy… woof. It feels like summer goes by too quickly every year, but this year especially with the anxiety of “virus variants” and “virus breakthrough cases” looming over everyone, it feels like it has completely flown by. I hope you’ve managed to do it up well, and travelled and gathered, and hugged a lot of people anyway, just in case things are restricted again come fall.
A quick personal update - the nomadic life might be coming to an end soon! We signed a lease in San Francisco to start after Labour Day (also refusing to omit the ‘u's, shut up America). It’s been a very excellent adventure so far, (and thank you to so many friends and family members for hosting us), but it’s time to settle into a more permanent mailing address, hang up some clothes, and even repay the hosting favours! (ha.)
This week in the newsletter, we’re talking about taking time off in your career without another specific job opportunity lined up afterward. Not all gaps are the same, to be sure.
I want to distinguish between the different types of resume gaps vs the one we’re exploring in this newsletter. Which is different from:
Sabbaticals (which are breaks from a job that result in you returning back to that job)
Involuntary gaps (being laid off, or leaving a job where it wasn’t your choice to do so)
This week, we’re exploring the concept of quitting without a ‘safety net’ of another job lined up. I’ll explore those other concepts in future editions of the newsletter (including thoughts on how to explain some of those other kinds of gaps), but let’s start here. I think there are some concepts/pieces of advice that will translate from thinking about voluntary gaps to thinking about involuntary gaps.
Musings
I should caveat this issue of the newsletter by saying, I have no firsthand experience taking this kind of leap. I think that being a people pleaser, being a productivity fiend, and growing up with a parent that had a lot of involuntary gaps on their resume have always made me pretty nervous to take a big chunk of time off in between jobs.
Culturally, (both in terms of growing up in an immigrant Chinese-Canadian household, and also in terms of the culture of investment banking) taking a break from work was always somewhat frowned upon.
I can understand my parents’ hesitations, they could never imagine having the financial stability or marketability to just voluntarily stop working for a period of time.
In the investment banking world, the inherent culture of working all the time, and the badge of honour that goes with it, made taking a break seem impossible.
(As an aside, if you’ve ever wondered about the intensity of the culture at an investment bank, a group of first year analysts put together a “Working Conditions” survey and slide deck at GS earlier this year. The WSJ covered some highlights here.)
I do think the world is shifting though, even in the most demanding of workplaces. Years ago (when working conditions were even worse than they are now for investment banking analysts… i.e. no protected weekends), news outlets wouldn’t cover this type of overworking as a bad thing. The unspoken agreement was, you learn more and make more money in this grueling industry than you could otherwise in any other job, so you don’t have a right to complain.
Nowadays, taking entrepreneurial risk is much more highly regarded. Tech companies value their employee well-being (and compensate them well). Mental health is more comprehensively considered by employers across the board.
All this to say: conditioning early in life and early in my career have caused me to have some remnants of the belief that taking time off will be perceived as slacking off, or being lazy… so I was really curious to talk to folks in my network that had taken time off, and to discover how thoughtful they had been in making the decision, and ultimately how their time off was perceived when they went back to a new role.
More on that below!
Conversations
It turns out I actually have a ton of really smart, successful people in my network that have taken incredible, enriching breaks. I tried to solicit a number of different views:
Someone still in the middle of their break
Someone who is on the other side of taking a break
A professional recruiter, and how she assesses people who have taken a break
I’ll start with the major caveats and practicalities here. Two very important questions to start with, and are simple to answer quantitatively. (and therefore correctly, because math does not lie.)
Divide how long you plan to take a break for by the number of years you’ve been working. If you’re a first year associate somewhere, and you want to take a year off, at the end of the break, 1/3 of your entire working career to date will have been a ‘break’. This is likely to raise some eyebrows. There’s a tradeoff here, obviously - a break might be most valuable to you when you’re younger/earlier in your career/more able to explore, but if you’ve only worked a few years, you haven’t quite ‘earned’ the right to stop working for a long time.
Is a break financially feasible? Budget for the full time you plan to take off, and then add a 20-30% buffer (because my guess is, when you are on a work break and don’t have a tangible reason to say no to things like trips etc, you will need said buffer). Do you have the savings required to cover the time off comfortably? Can you pick up some work or projects during your time off to supplement your savings if needed?
Those two points above are very important to offset stupid applications of advice like “Just follow your passions! Live your best life!” Listen, I, too have a “passion” to live on a yacht and not work, but that is not realistic, and probably pretty damaging to my personal finances.
One more question, that is hard to quantify, but important to consider - assess how marketable you currently are. What is the macro environment? Are you working in an industry that is net growing or shrinking? Will there be similar jobs available in 6-12 months? For certain technical folks (software engineers, for example), job security is almost guaranteed, so taking time off is an easy decision. The tides rise and fall and job availability in certain industries change for reasons outside our control, but this is important when it comes to the timing of taking time off.
Ok. Onto the fun stuff. Actual thoughts and advice:
A friend who spent 5 years at an investment bank, then 5 years at a large tech firm, and is currently looking for the next thing:
“It wasn’t by accident that I chose to work at 2 of the largest brand name companies for the first part of my career. It’s my insurance policy - working for two great companies signals implicitly to all future employers or stakeholders that I’m credible and that taking a break was my choice.”
“In order to make the decision to take time off, I asked myself, “Is my toolbelt full?” Have I acquired the experiences and skills from these two jobs that I can now use those tools to iterate on what I want to do next, or is there an experience I’m missing that I need to do first? I checked in with myself a few times over the last 2 years of working for an employer - it wasn’t an impulse decision at all.”
“I knew I wanted to do something atypical next in my career (i.e. not corporate), but I couldn’t figure it out while working at my last job, and not just because it was demanding. More than that, I cared a lot about the last team I worked with and didn’t want to give them 50% of me while I started work on my own business idea.”
From a work contact who worked extremely hard, travelling everywhere in the first 10 year of her career, and then took time off to have children (twins!)
“I didn’t want to balance raising twins while flying everywhere, so I took a full step back for two years. Obviously no firm in finance can guarantee that I’d have a job after two years, but it was worth taking that risk for me. I had worked basically two jobs for 10 years, so in my head, I felt like I had earned the two years off, guilt-free.”
“I guess, in my own way, I hustled while taking the time off. I stayed extremely up to date on the private asset market. I had monthly check-ins with my former bosses at my last two funds. When my kids were a bit older, my former boss was leaving to start his own fund and invited me to join. ”
From a financial services recruiter who assesses resumes in their talent pipeline from associate up to partner-level candidates:
“It is still frowned upon for junior people (<5 years work experience) to take time off. There’s no way to sugarcoat that."
“Time off is contextual. What is the broader story of the candidate? How branded is their experience?”
“What are they using the time off to do? Are they working on specific skills, a specific startup idea? The more structured the story is, the more compelling it is to see the sabbatical as an experience as valuable as any other job.”
A contact who was a CTO at a mid sized tech startup who took a year off before starting his own company :
“I’m really fortunate, my profession (CTO) is very in demand and very well understood, so I probably didn’t have the same apprehensions of worrying about not being able to find a new opportunity.”
“I took time off because I wanted some inspiration and direction on what I wanted to build next. I was getting really good at building things for other people, and I was starting to lose sight of what I was personally interested in working on.”
“I spent the time travelling to different cities and reconnecting with a ton of friends to hear what they were working on and what energized them.”
“One of the most valuable things I did in my time off was build a non profit app - something that had only myself as a stakeholder, without the demands of others/board/investors. My aim wasn’t to make money with it at all, it was more to take an idea from conception to execution on my own terms for a cause I was passionate about. It turned out to be an incredible way to set myself up for what I did next: some of the technology I built ended up translating right over into my new company.”
In summary, some of their thoughts to leave you on:
Solve for fun and fulfillment: Everyone that I talked to about a career break, unanimously agreed that it was one of the best decisions they made. Lots of fun was had, lots of places were travelled to. Yes there’s some planning and foresight that goes into the break, but it’s most important to be present in your break, immerse yourself in whatever you spend your time on, and enjoy it!! You rarely get such undisturbed time to reflect and create.
Branding on your resume early on in your career matters: it points to a vetting process done by trusted, successful companies. It’s not the only thing that matters, but for reference, I spent ~15% of my career at Goldman Sachs, and many people in my industry still introduce me using that logo as one of my many jobs. Strong company brand initially buys you some flexibility for atypical choices down the road.
Goodwill with your previous employers and network pays dividends down the road: Those that have worked with you in the past and think you’re great won’t care that you’ve taken time off, and when you’re ready to go back, will likely have leads on the next thing (or welcome you back themselves). But you have to take action to in front of great people and great opportunities, and not expect things to come to you. When you’re out of the flow of an everyday job, you need to structure outreach or updates to connect with those people in your network.
Time off is a great opportunity to network in a smart way: I wrote about this concept a few months back and defined networking not as asking for things from others, but instead offering your services to others. When you aren’t working, you have tons of things to offer - your skills and time. Find people that are energized, or working on things that you’re curious about, and see how you can help - in return you’ll get some insight into what you want to do next and how you might approach it.
I’d love to hear from you if you’ve taken time off, or if you’re planning to take time off and what other advice/tips you’d give those that are thinking about it
Resources/Links
Cool Ladies Doing Cool Things: Forbes published their list of America’s Richest Self-Made Women there are so many badass women on this list spanning different industries. Very good inspiration! (One thing I do not understand is why people on the Forbes lists are asked to disclose marital status and number of kids, on one hand, it’s interesting to learn about their broader life, but on the other… is it relevant?) (Forbes)