Back to School, Back to School
Back to School, Back to School
G'bye Summer!
Hi all!
Suddenly we’re in the first few weeks of September, on the other side of Labour Day… summer is definitively coming to a close. I know this for a fact, because when walking through the airport last week, I was accosted by signage reminding me that Starbucks has officially started pimping its annual array of holiday themed beverages.
(FYI, v important news, there is a threat to the reign of of the PSL - something called the Apple Crisp Macchiato? Sounds kinda gross, but… I’d try it.)
Even though I am not personally in school, nor do I have children that are back in school, September always has connotations of a fresh start. It will not surprise you to know that growing up, I loved everything about back to school season - especially back to school shopping…(for new school supplies, not clothes).
It’s always around this time of year that I feel like I want to learn something new, or set new goals at work, or shift into a higher productivity mindset. I don’t think people are meant to work at the same intensity every single day of the year, and similar to physical fitness, there should be guilt-free seasons of resting more vs. seasons of working harder.
Maybe your summer was full of wrangling kids into various summer activities, maybe your summer was full of reuniting with friends and dipping a toe back into travelling and vacation, and now you too have the same nerdy excitement about September and fall goals.
I, for one, have been woefully inconsistent in writing the newsletter over the summer, and September feels like a good time to recommit to writing on a weekly basis.
So, let’s get into broader thoughts on goal setting! I will try to avoid cliches, like this one:
My personal approach to goal setting used to be very tactical.
If you know me, you know I am a life admin maniac. When I wake up in the morning, I reach for my phone and immediately start answering messages, booking appointments, ordering multivitamins on Amazon… in a weird way, I find checking tasks off a list oddly soothing.
My goals list would often look like this:
Train for a 10k race
Get promoted in x months
Take a writing course
And every few months, I’d check in on progress. I’d feel guilty or anxious if my goals weren’t met, and I’d likely replace the list of goals with new, refreshed ones. I’d adjust the timeline, or the specifics, but the list of goals kind of felt like an ongoing to-do list.
As I’ve done research for this newsletter and met various successful, productive people, I’ve come across different frameworks for goals that go a level deeper than my own tactical approach. As I dug into them a bit, I realized that even though my list of goals continued to grow, they always felt a bit aimless. My goals were tactical, with not much deeper meaning.
In the nomenclature of the first framework below (Simon Sinek’s “Start With Why”), my goals were all ‘whats’. Conspicuously missing from my goal setting exercises was the backdrop of why.
And in the nomenclature of the second framework below (Angela Duckworth’s “Hierarchy of Goals” ), I was mired in the short term action goals, vs. the overarching visionary goals.
I’ll explain a bit more below, and then offer an approach to goal setting that marries tactical goal setting with the broader why. If you find this kind of stuff helpful, let me know!
The “Why”, First
We start with what Simon Sinek calls, “The Golden Circle”.
Simon Sinek’s speech here:
The cliff notes version:
Most companies and people who believe themselves to be successful have no problem explaining what they do:
“I work for a top tier investment bank”
“I code software for consumer tech company”
“I’m an MBA student”
And some people can tell you how they do what they do: their differentiators, their competitive advantages etc.
Fewer people are in touch with the ‘why’. And Simek’s philosophy is that the why is all that matters.
Goals, since they are abstract and aspirational are similar. Many people can tell you what they want to accomplish, and even how they want to accomplish these things, while the why is unknown or secondary.
The same is true of companies. When I joined my fund, our mission statement described what we did: provide capital to transformative innovations in healthcare. Not a bad mission statement, but it lacked something broader.
As a team, we collaborated on reworking our mission statement according to Simek’s principles. After watching the speech, our team started digging into our individual ‘why’ statements. It turned out that there was a high degree of overlap in everyone’s ‘why’s. A lot of the team started working in healthcare to improve patient outcomes or quality of life. Many members of the team were motivated by having broad impact.
The next level down, the ‘how’. The team delved into our best practices, or fondest experiences of working on a team, regardless of what the team was working on. A few common themes emerged: working with high-integrity people. Working with smart people. Feeling respected.
We spent the better part of an hour identifying these themes before tying it back into ‘what’ we actually do… which happens to be investing in healthcare. It turns out, the ‘what’ was pretty minor in comparison to the ‘why’, and even the ‘how’.
If members of the team were forced to change their ‘what’, for example, (i.e. didn’t work for a healthcare fund), they likely would have found different ways to work with high integrity people to create positive impact through health outcomes, and still felt largely fulfilled.
Some would have been physicians, others would have operated a healthcare company, and others would have volunteered for a health focused non-profit in their spare time.
Simek uses the framework to describe Apple, and other incredibly successful, innovative companies:
“Remember, people don’t buy WHAT you do, they buy WHY you do it. If a company does not have a clear sense of WHY then it is impossible for the outside world to perceive anything more than WHAT the company does.”
I think the same reasoning can be applied to individual goal setting and conviction. Most of us aren’t purely motivated by the what and the how, it’s the why that we connect with, that drives us to action.
Furthermore, the what is subject to change. What Apple is, has morphed and shifted over time - computer manufacturer, consumer electronics manufacturer, smartphone pioneer, streaming services… but why they exist, to continuously think outside the box has never wavered.
The Hierarchy of Goals
In my newsletter on the meaning of grit, I talked about what Angela Duckworth, psychiatrist and author of the book, Grit, describes as a “hierarchy of goals”, that successful, ‘gritty’ people live by. There are short term, tactical goals that underlie medium term goals, that underlie overarching ideological goals.
Duckworth maintains that this model of pursuing success never loses sight of one’s overarching ideological goals, but allows for plenty of flexibility in deviating from lower level/tactical goals in the short term as means of finding different paths to the longer term goals. In other words, we might not always relentlessly achieve the short term tactics, but that isn’t a failure. If we maintain focus on the overarching, ideological goals and utilize flexibility and agility in finding different paths towards that same vision (which implies abandoning some previous paths), we are actually exemplifying grittiness.
Duckworth’s personal top-level goal is “to increase psychological literacy”, which she has contributed to through all means of research, writing and teaching. She discusses with Steven Levitt (the author of Freakonomics and the host of the Freakonomics podcast) his abandonment of academia to produce the podcast, which he initially views as potentially an abandonment of his original goal. Through their discussion, he reframes it, realizing that his top-level goal isn’t necessarily success in academia, but it’s to evaluate complex problems from various angles and reach a wide audience with his insights.
Listen to the podcast here: https://freakonomics.com/podcast/goal-hierarchy/
Putting it into action
Before you write down any singular goal, start with the why.
On a piece of paper, or in your phone’s Notes app, write down 5-7 of what you believe your values to be. Maybe you’re not like Angela Duckworth who has a succinct mission statement as your arching goal yet, but chances are you have a pretty good sense of your core values.
(By the way, it’s completely normal to not know these off the top of your head. I definitely started by Googling “Core Values” as inspiration.)
Check these out: https://scottjeffrey.com/core-values-list/
As you read through this list… chances are a lot of them are going to sound pretty resonant… but be brutally picky, you can only choose 5-7. If any one sounds more specific or appealing than another, pick it and move on. You might write down 10-15 to start, but then as you keep reading through, asterisk the ones that really resonate with you. I’ve done this exercise with friends and colleagues (aka people that I think myself to be similar to), and it always surprises me how different our shortlists end up being.
This list may change over time, but I think it’s a pretty good framework to save in an easy-to-access location, and check in with from time to time.
Step #2:
For each of the 5-7 values, give yourself a rating from 1-10 of how aligned you feel like your life currently is with each of these values. It doesn’t need to be scientific, just an overall feeling of how much you feel like this value is being lived in your life.
Step #3:
For each of the 5-7 values, draw two columns, and assess:
Where is this value strongly showing up in my life?
Where is this value underrepresented (or worse, being violated) in my life?
I’ll pause here to give you an example from my own list/goal setting exercise.
One of my core values is: Positivity. I admire this trait in others, it is a preexisting condition to productivity, it’s something I think others value in me, and is correlated with other core values of mine (e.g. empowerment, connection).
This value shows up in my personal life: I hope that I serve this value in my friendships, with my colleagues
This value shows up in my professional life - often in teams, or with external stakeholders, I am tasked with developing positive relationships between people, seeking alignment and compromise.
Step #4:
Reaffirming goals
In areas where you’ve given yourself a high rating, in areas where the value is strongly showing up in your life, keep investing. These are where you are most strongly aligned and what is reaping success in your life.
For me, my value of positivity (the why) shows up in writing this newsletter (the how). I love putting something out in the world that people can relate to, or can help reframe something. The what, or the goal itself, is committing to writing the newsletter more frequently, and to focus on specific topics that you’d all find helpful.
Improvement goals
Look at the areas where you’ve given yourself a low rating. If this is a value that’s important to you, where are you falling short of living in alignment with this value? What can you do to close the gap a bit?
My value of positivity (again, the why) is currently hindered by my general energy level (traveling, seeing friends, eating and drinking all the things, sleeping poorly). I’m my most upbeat, productive and positive when I’m in better physical shape, so I’d like to focus the next month on eating and sleeping better.
The ‘what’ of eating healthy has been on my goals list in some way shape or form for the better part of my adult life, but the framing it in context of the why/my values will almost certainly keep me more motivated
Resources/Links
The cliff notes version of Simon Sinek’s “Start with Why” (Medium)
Cool Ladies Doing Cool Things: Annie Vang is a Hmong woman building an app to preserve her cultural history and language (Elle)