Letter 007 - Having Multiple Jobs (no, it doesn't have to be at multiple organizations)
How experiences outside of your core "day job" can actually make you way better at your day job.
For the last 4 or so years, I’ve largely avoided caffeine. I’ll share the story on why I shifted mostly to decaf coffee another time… But this past weekend, I YOLO’d. I had two cups of coffee over brunch with two of our friends here in ATL. It was 3pm. I thought I was safe. I wasn’t. Fast forward 12 hours, and I was still wide freaking awake.
As I lay awake, I played back the last decade of my life, honing in on the key decision points. During this moonlit exercise, I remembered the first time I got a competing job offer (about 1.5 years into my career). I remembered the excitement. I remembered the conviction that it was the right thing. And then I remembered the moment when I realized that it was absolutely not the right move to make. That realization forms the basis of point 1 of this week’s letter…
So what are we talkin’ about this week?
Experience & Learning are a form of compensation
Rate of Learning (RoL) is one of the most important factors at work
There is immense value in having “multiple jobs” (note: this can be at your current company)
1 | Experience & Learning are a form of compensation
The thing about work is that you are compensated in ways that go beyond near-immediate cash. I’d argue that how you feel at work (see last issue for a bit on this), and how much you’re experiencing+learning at work are also forms of compensation.
About 1.5 years into my career, I almost left consulting to join a large corporation. I was fortunate enough to get the job, where I would be doing one thing, and be paid 30% more than I was making at my consulting firm. This was a super wonderful opportunity on the cash vector, but I turned it down.
The reason I eventually turned down the job was because when I asked myself the below question, I couldn’t give a resounding YES.
“Is this new opportunity going to be a superior learning platform? Am I going to get a wider range of experiences there?”
The answer was no. The job was compensating me more on the cash vector, but asking me to take a cut on the experience + learning vector. A “cut” that I knew would damage my long-term optionality. I wasn’t about to take a bet against my future like that.
Over the next 5-6 years, I would get to know a bunch of different organizations who were almost always willing to pay more, but could not give me a “raise” in terms of experience + learning. I eventually did find this through joining a startup, and only then did I leave one platform to join another.
2 | Rate of Learning (RoL) is one of the most important factors at work
OK, so you finally find an opportunity where the economics make sense, you enjoy the culture, and you will have access to a range of experiences and the learnings that come from them. Great! But there’s one more thing that matters here… the rate of learning.
Remember that Rate = Distance / Time. Perhaps a platform can give you access to an astonishingly-wide range of opportunities, but it’s going to take you 30 years to experience said range. That would be a High Opportunity, Low Realization environment. I prefer High Opportunity, High Realization environments.
Put more plainly, it is oftentimes advantageous to seek out environments that will allow you to quickly gain access to a range of experiences. This speed has a compounding effect. Just like you can achieve substantial compounding benefits from maxing out a 401(k) early, the same applies to the range of experiences you’re getting at work in a timely manner.
(Note: I will write another letter in the near future on how to actually go about getting many different types of experiences without burning bridges… but one key spoiler alert note: not all bridges are meant to be maintained…sometimes the advice / energy being sent across the bridge, so to speak, are actually harmful).
3 | There is immense value in having “multiple jobs”
Disclaimer before I go any further: Energy Management (yes, another future issue) is an extremely important thing. The risk of burnout is real, and I think it essential for us to consider what we can reasonably balance before committing to additional responsibilities. With that said…
Having multiple jobs / roles can be incredibly valuable for making sure your Rate of Learning stays high over time. Here are some examples + anecdotes:
This oftentimes takes the form of having your core responsibility at work, and then having another “extra-curricular” (so to speak) role. One of my lifelong friends (I call her JC) has her core job and then simultaneously leads a badass Women’s Network at her company, where she has played a role across every aspect of the now-annual program — I think it’s now in its 7th year!
This can take the form of serving on a non-profit board. For many years, I served in leadership positions on non-profit boards, doing things like: recruiting, fundraising from people, helping to put on events, promoting these events, thinking about the branding + experience for the entire organization, thinking about pricing, thinking about stakeholder management, interfacing with the more senior board, considering how to grow in the marketttttt WAIT A MINUTE, aren’t these all things that most organizations have to do? Yes.
For those aspiring to general management positions, where you hold responsibility for an entire group/organization/company, you’ll likely have to do a wide variety of things every day that have overlap with some of what I just laid out from a not-for-profit context
For college students, this oftentimes looks like running a club, being president of an organization, etc. etc.
Trying to start a new product or business line at your company. I built on confidence gained from failing + succeeding in the non-profit space to pitch more holistic, well thought-out, realistic ideas to my past company. Sure, most of the ideas were turned down, but even trying to have them get sponsored led us to meet some interesting leaders (who then became mentors).
It’s no accident that many senior leaders and CxOs serve on the boards of other companies. They get to see the entire operations of another organization in real-time…learn about what is and what is not working, and then bring that elevated awareness and understanding back to their core responsibility as (insert executive title). Many of the founders and CEOs I know sit on at least one board or advisory committee of another organization, if not multiple
Today, I spend many of my early mornings, late nights, and weekend mornings working closely with startup founders / people building out young companies. Beyond the fact that I find it extremely fun + fulfilling + fascinating, I oftentimes discover a new way to think about or view a problem… ways that (I’m convinced) make me substantially more effective at my core day job. I will say that you need to manage this carefully with your core organization — in my case, I am unbelievably fortunate to work for a company (Ally.io!) that is supportive of this.
And again, I cannot emphasize this enough — you have to manage your energy. There are oftentimes weeks where I don’t have the bandwidth to do non-profit board work or VC stuff… And when those weeks happen, I am forthcoming about my situation. And there will again be phases of my life where I can’t sustain the pace on multiple fronts, and need to pull back. I’ve done it before, and I’ll do it again.
I also have a pretty brutal practice of basically turning off my phone for most of every weekend, because my brain needs a break on a regular basis. I find it very challenging to basically ignore e-mails / texts / calls for that duration of time, but it is honestly one of the only ways I show up with big energy almost every Monday morning
Pursuing your own hobby / project. One of my wonderful coworkers has written books + launched a whole platform on salary negotiation (link here), and I know the experience of doing this had positive “spillover effects” into his day job. He demonstrated incredible consistency in these pursuits, and continues to invest time into it!
I’ve framed the above conversation in the context of work, but I also want to take a step away from this thread of the convo to say that there’s a “role” or “job” that is missing from the above list, but that likely delivers some of the most badass learning + growth out there: Being a parent. A very close mentor of mine (Mom of two, global partner back at Deloitte) oftentimes would share stories about how being a parent made her a better leader, and I see examples every single day. My core manager at my core job (Ally) amazes me on a weekly basis with how she balances running an increasingly-complex organization with being a mother of three (yes, she is as badass as she sounds).
Which leads me to the closing point: who you work for matters. They in many ways can enable or destroy the potential for high rates learning. If you work for great leaders, they’ll work for you, too. They’ll constantly look out for ways you can grow, they’ll coach you as you pursue growth, and they can help you keep your rate of learning high, which can even mean helping you evolve into a different team/unit/company altogether).