To All the Jobs I've Loved Before

Thank U, Next

Hi friends,

Thanks for the feedback on last week’s post about getting back into a routine with the newsletter. You all have many stories about being perfectionists and experiencing the cognitive distortions of binary thinking, and I’m glad you found the post relatable. I also talked about seeking evidence to the contrary - and turns out, taking almost a month off of writing the newsletter did not render it obsolete. So thank you, dear readers. You are the best, and it’s a privilege to be in your inboxes 🤗.

We’re heading into Thanksgiving here in the US which in some ways is a bigger holiday than Christmas (not religiously linked, typically two guaranteed days off) which always signals to me the closing of the year. I’ve been in the US for almost ten years now, and being Canadian (and celebrating Thanksgiving at an earlier time of year, which makes perfect sense since it’s not smushed up against Christmas, but I guess you can’t really change the date of the Mayflower arriving in the US), I don’t have typical family obligations, and instead enjoy time in the city (previously New York and now San Francisco) when it’s quieter. I am looking forward to spending lots of time with friends who are also international in origin and therefore also Thanksgiving orphans.

This week’s subject line is a reference to the BEST MOVIE NETFLIX HAS EVER MADE:

Don’t you dare tell me otherwise. And don’t tell me this was made for tween girls. Or that YA fiction isn’t worthwhile reading. This trilogy was great, and Lana Condor is a real gem, and both my teenage and present-day heart runneth over with joy at this delightful Asian American representation in mainstream media.

The quick plot synopsis, is the main character, Lara Jean, writes letters to all the boys in her romantic past (she is like 16 in the movie, so it’s an appropriately short list) to get all her feelings off her chest, and one of the letters leads ultimately to an adorable love story.

If you know, you know 😍

Anyway. Over the next few weeks with the newsletter, I want to explore the topic of career switching! It’s a topic that I’ve spent a lot of time thinking about, and living through. If you’re new here or don’t recall my career background, it is a veritable mess of twists/turns and changes…

My version of this involved less going back to school, and more switching jobs every few years.

My LinkedIn makes it look slightly more streamlined, but the internal decision making progress, and the bouncing around has been anything but.

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I had a few encounters/reflections these past few months that made me think about my nonlinear career path in a new way.

1. First, I passed the second year anniversary of being at my current firm. If you scrutinize my LinkedIn or CV, you’ll see that my typical stint at a given role was around two years. It’s the first time in a while that I haven’t been in the middle of a job change or career shift (or even remotely thinking about it).

2. Second, as I gave my background/intro on a client call for the umpteenth time in my career (always a bit awkwardly, stumbling through my multiple experiences), the client responded succinctly with, “Oh so you’ve always been in these kinds of roles.” which I found surprising, because I’ve never thought about my mixed bag of experiences as really that cohesive.

3. Third, I was paired with a mentor through a conference that had an eerily similar background to mine (traditional financial services, asset management, business development, people, operations) and is now in a senior role at a global asset manager. It seemed like proof from the universe (don’t snort at my hippy dippyness pls) that despite the twists and turns, there was a viable and successful path analogous to where mine appears to be heading.

I used to be really self-conscious about moving from role to role, and in a short time frame. There’s always the cocked eyebrow from an interviewer, or the feedback from a recruiter (“You’re a bit of an atypical candidate”), or the long winded intro/explanation to give, compared to your colleague that summarizes “I was a banker for 4 years and I’ve been investing since.”

But I’ve noticed that increasingly (and especially in tech roles in the Bay Area, where I am based), people switch jobs more frequently. And the data supports this:

Over the last 20 years, the number of companies people worked for in the five years after they graduated has nearly doubled. People who graduated between 1986 and 1990 averaged more than 1.6 jobs, and people who graduated between 2006 and 2010 averaged nearly 2.85 jobs. (LinkedIn)

And while I have some amount of shame/self-consciousness around my career switching, I can’t help but feel like there are strong positives to the transitions that I’ve made to date, that might ultimately have resulted in my feeling more settled in my current role. While the external perception of career switching has improved, if it doesn’t lead to more internal satisfaction, then is bouncing around really a great move?

Get ready for the most eye-rolling, hippy-dippy comment ever, combined with (my favorite, a career + dating analogy)… but you know how in dating, every person you meet/date that isn’t “your person”, brings you closer to your ultimate person?

EVERYTHING HAPPENS FOR A REASON, FAM!! 🤩! 🤢?

I won’t lie, there have been roles and companies that I’ve been really ready to leave, but in retrospect, they’ve all provided valuable experiences, that have in small ways contributed to some element of self-discovery, and illumination of the things that I like to work on and am good at, and the things that I am not so good at, and should either learn to do, or outsource (revisit my post on weaknesses here).

And if you’re reading this newsletter on a precipice of wanting to make a career change, and feeling a bit overwhelmed… I think a good starting point is to take inventory of your past experiences to date. You can ask around externally for all the advice in the world, but you know yourself better than anyone else, and your own assessment of what has worked well for you in the past and what you’d look to replicate in the future is going to be a valuable starting point before getting external feedback. You can start to tease out the commonalities, the interests, the highs and the lows, without the noise of what you should do, or even what’s in the realm of possible.

So, in the vein of the POET Ariana Grande, shouting out her exes:

I thought I’d run down the list of my career experiences, and what they’ve contributed to my self-understanding and what I now seek in my day to day.

(PS. Are you wondering which one of my past jobs is the Pete Davidson (famous Ariana ex) of jobs? That job that most of your friends and family are like, “Girl why would you take that job? That’s a terrible life choice”, but one or two are like “Damn girl that’s so cool.”… Basically, Pete Davidson is a gig at a hot NFT startup.)

YES BUT WHY AM I (AND SO MANY OTHER SELF-RESPECTING WOMEN) SO ODDLY ATTRACTED TO YOU.

And in the vein of Thanksgiving, and expressing gratitude for past experiences, a shout out to things I’m grateful for with each experience and what I’ve learned. None of my earlier jobs probably would have been a good long-term fit, but with each role I got a bit ‘smarter’, or at least calibrated on what I was ultimately

• Bulge Bracket Financial Services Firm #1 and #2:

  Grateful for:

  • Doing things with precision and attention to detail. Even though it sucked checking every word and footnote (in a presentation it was unlikely people would fully read), it instilled a standard of quality work in me that would have been hard to replicate

  • Working with really smart people. People took pride in working for a big, well-respected firm, and that pride can elevate each other

  • Brand. This is a big one. To this day, almost a decade after my first finance job, I still reference these logos when introducing myself (even though I was a pretty lowly minion at both places). I’ve connected with people based purely on having both worked here, and it’s a starting point of credibility for those who value such things.

  Learnings:

  • Purpose. Working on high-paced deals is exciting, but at the end of the day, shuffling capital around didn’t really resonate with me.

  • Smart people aren’t always nice people. Some of the really smart people I worked with were wonderful, others had high egos in a culture that rewarded ‘stars’ vs collaboration

• Tiny Mess of a Startup #1

  Grateful for:

  • Learning how to managing chaos. I serviced loans out of a Google doc, and on any given day I knew how much was in our operating bank account to the penny. Putting systems and order around chaos gave me peace of mind

  • Excitement. This job felt unencumbered by rules (and in some ways reality, unfortunately), but it was extremely appealing to go straight-line from idea to launching something without a ton of bureaucracy

  Learnings:

  • People can be both not smart and not nice. Even more so than in a large corporation, the culture and ego of the people in a small company are critical, and I did not do enough diligence on this point before joining.

  • Results matter more than brand. This company had a fully retained PR firm before they had found product market fit which should have been red flag number 1 that this would not be a cultural fit.

  Emerging asset manager

  Grateful for:

  • Being valued for being a generalist and an empath. I had the opportunity to work cross-functionally, and fix some problems not only with processes and data, but with communication and empathy

  • A great passionate team. Very smart, very established people who were humble, kind and liked having fun together.

  Learnings

  • High growth can be too high. I liked being surrounded by optimistic, ambitious energy all the time and feeling like everyone was making great strides in building something, but as the business grew, I started growing horizontally, not vertically. i.e. I was spreading out doing the same things multiplied over numerous business lines as we grew, vs learning more skills and feeling upward momentum.

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Across all my job experiences, a few foundational things stuck out to me that weren’t necessarily tied to any specific skills:

• People really matter to me, humility in particular is important to me

• I like roles where I can play different roles and wear different hats

• I like the rigor of finance and data, but I like creating a story around it more than being mired in the details of it

• I want to build something that has a net positive impact on the world but am willing to be very open minded about what that means

And when I cross check with my values (see my post on values-based goals here): positivity, efficiency, reliability… it all kind of checks out.

Things I did not want to take into future roles with me:

• Large egos. No matter how smart, how accomplished, how high-growth, how sexy the company or role is, this is non-negotiable

• When chaos is too much chaos. I love solving ambiguous problems and putting order around things, but feeling like I was drowning in uncertainty and not making forward progress was and is very challenging for me

This isn’t to say I have it all figured out, and I’m certain my criteria will continue to evolve and change, but taking inventory and drawing out some specific, recurring themes helped me feel more intentional in my career and closer to obtaining a sense of satisfaction.

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Resources/Links

• When thinking about career changes, start here: Look at the side of the list that describes Internal Qualities…What things are you good at that transcend actual job structure? (Top Resume)

• Common Myths of Career Switching: Spoiler: you don’t need to massively blow your life up. (Intercoast.edu).

• Cool Ladies Doing Cool Things: “25 Famous Women on Starting Over in a New Career” (Vulture) Did you know? Ina Garten (host of Food Network’s “Barefoot Contessa” and food diva/personality extraordinaire) previously worked in nuclear energy policy! Elizabeth Warren was a teacher! Dream big, ladies.