LSW#30 📜A Manifesto for Thinking Differently about Careers
35 unconventional career frameworks
The standard way of thinking about careers is analytical. It’s the classic weighing of pros and cons, and thinking with a “cool head”. Except when it comes to truly life-changing decisions, all logic goes out the window. The decision-making becomes more existential, rather than logical.
In 2021, I walked away from a successful 20-year career in engineering and management. Unlike what’s commonly portrayed, it wasn’t an epiphany that “struck” me, but rather an accumulation of realizations.
Thinking clearly became a premium because of the high-stakes involved. Over time, I collected a range of frameworks that helped to cut through the Gordian knot of my own thinking.
I’ve written a long-form article capturing these ideas. I also created a downloadable resource (links at bottom of this post). Below is a synopsis of that piece.
Go for options that enlarge you, rather than those you think will make you “happy”. We are bad forecasters. Often, happy equates to safety within known limits, which also means a lack of growth.
What might be optimal today, is sub-optimal when taking the long-view. Choose trajectory over optimization.
We forget that foresight is limited, but we have unlimited hindsight. This means we try to figure out everything upfront, and beat ourselves up for mistakes in the past. Remembering the asymmetry between foresight and hindsight is useful.
You are contemplating a significant decision. It’s causing a lot of anxiety, even ambivalence. It’s not clear-cut. Most important decisions never are. The mistake is to use the anxiety and ambivalence as criteria to dismiss options.
Writing your obituary might sound morbid, but is a useful exercise for gaining perspective. Morbidity is the point.
Maximizing chances of success often conflicts with minimizing regrets. The safe option might guarantee success, but it doesn’t mean you won’t regret not taking that speculative shot. Regrets start looming larger with passing time.
Buridan’s ass died from indecision between a pale of water and a pile of hay. The status quo is a decision in itself.
Most of us have an “inner ring” we are chasing, including yours truly. Each time we go one level deeper, we find the next one. We are always the outsider. The inner ring is a hoax.
Is your decision reversible or irreversible? It’s what Jeff Bezos calls two-way vs one-way door decision types.
For too long, I was chasing guarantees. There aren’t any. The sooner we realize that, the faster we can move. We want to go to heaven without having to die.
Ben Franklin got many things right. But from the perspective of careers, he got it all wrong. Time is NOT money. They are fundamentally non-interchangeable.
We want freedom, but not the discomfort and insecurity that comes packaged along.
Obliquity as a strategy has been forgotten in modern culture. We chase happiness and success, only to find them fleeting. You can only achieve them indirectly.
Thinking about decisions is not decision-making. Taking some action, even suboptimal ones, is true decision-making.
What’s gotten you excited today, might not do so in a year, let alone 5 years. Ambitions are like fruit. They rot if not acted upon soon enough.
Hollywood and culture romanticize big decisions and giant leaps. They hide the “figuring out” of things. What’s often more practical and effective is small steps.
We look for the “right path”, not realizing that it becomes “the path” only in hindsight.
Money dominates our thinking, especially in careers. What’s forgotten are the more important criteria of : Identity, Energy, and Time.
The notion of “looking for” purpose is misguided. It puts agency outside of us, and elsewhere. It’s our job to “create” it.
Often things get murky because we are trying to thread the needle. What do the extreme options look like? That can create some clarity.
It’s easy to buy into the “tyranny of the OR”. The “genius of the AND” might be hard to pull off, but it’s doable. BENTO is one way to think about this.
Culture programs us to maximize everything. What’s often more effective is Herbert Simon’s notion of “satisficing”.
We confuse risk with uncertainty. One can be minimized, almost eliminated. But the latter is ever present and not going anywhere.
Planning is a helpful notion when operating in known domains. But in uncertain territory it becomes an impediment and excuse for inaction. “Crafting” is a better construct.
Another confusion that trips us up is not differentiating between objective risk and subjective risk. One can kill you, while the other is more psychological.
Not knowing “how” is ok. Don’t let that stop you. Knowing why is the more important piece.
Going after what you care about is not necessarily “normal”. It’s in the interest of society for you to act and behave a certain way.
Upside usually comes packaged with the downside. You cannot just sign up for one and not the other.
What might look the safest, can also be the riskiest.
Society programs us for “having” and “seeming”. What gets forgotten is who we are “being”, or who we are “becoming”, in getting there.
There are 4 primary human drives. Often frustration in careers happens because one of these drives is not being addressed, or in conflict with each other.
Sunk costs have kept more folks in unfulfilling careers than probably any other factor. Don’t jeopardize your future to respect the past.
We all have a story. It’s mostly hidden. Bringing it out, and making it an object, that then can be subjected to revision and different interpretations, can help immensely.
Same for assumptions that are hidden but restrict us regardless.
Decision-making is put on a pedestal. But for many scenarios in life and work, it’s mostly useless. What’s actually useful is sense-making.
I realize this list is unconventional, even non-actionable. There are no step-by-step instructions or “guaranteed” formulas. Some points might need more context. You can find them in the main article (link below).
For them to work, you need to sit with them and grapple with the ideas. Working with a peer/mentor/coach, or even your manager, can be super useful. The frameworks can guide and anchor your conversation.
Leader’s Library
Here’s the link to the full article with a full reference list:
I made a quick reference pdf with all the frameworks that you can download:
That does it for this edition. Have a great week ahead!
P.S. I am out for the next couple of weeks for a summer break. Will be back in your inbox, the week of July 4th.