The tendency to underestimate our own resourcefulness

My friend recently switched from a small nonprofit job to a corporate philanthropy position.

When asked what the biggest difference was, she said:

It’s so refreshing to actually have resources. At my last job, people would yell at me for printing something in color.

If you’ve ever worked for a startup before, you can relate. Words like scrappiness and ownership aren’t clichés, they’re necessities.

Because in any bootstrapped environment, you don’t really have a choice. Everybody has to do everything, whether they want to or not, whether they’re busy or not, whether they’re expert or not. Otherwise it won’t get done and then the whole team suffers.

But the upside to this ethos is, you learn how to do a lot with a little. Startups put a constant wall in front of you that only ingenuity will allow you to figure out how to get around it.

Belsky, who founded the world’s most successful online portfolio software for creative professionals, summarized it fittingly during a recent interview.

Resources are like carbs, but resourcefulness is like muscle. When you develop it, it actually stays with you and impacts everything you do going forward. If you’re forced to develop that muscle, that serves you forever.

And it’s not that we don’t long for the day when some organization gives us an unlimited budget to execute our work. Perhaps some of us will have the good fortune of such prosperity.

But let’s not hold our breath here.

In the meantime, it’s best that we focus on developing our muscles. It’s like the transition from street performing to studio performing. When artists get their start playing in public without a net and without amplification, by the time they can finally afford to plug into that twelve thousand dollar microphone, their songs sound that much better.

Don’t underestimate your resourcefulness. Trust that in any given startup situation, you and your team will figure out how to tame the beast before it triggers the collapse of the organization.

How are you getting in touch with your own resourcefulness?

Drag me out into sea like an abandoned raft

One of life’s great satisfactions is leaving.

Making the decision that you’ve done what you needed to do, feeling complete about an event or experience, and then just walking out the door.

Without justification, without guilt, and without the fear that somebody is going to call you out for leaving when you did.

It’s so empowering. Because the tendency to stay longer than you want to is quite strong. There are cultural norms and social pressures and power dynamics at work. And like an undertow, they can drag you out into sea like an abandoned raft.

This is a boundary issue. The skill of leaving stems from your ability to have a secure, worthy and confident self. Knowing that you are a valuable and whole person, no matter what time you choose exit. You’re a mature adult who has your own life and you can do whatever you want, and your leaving makes others uncomfortable, well, people’s expectations are their problem.

You are responsible for your boundaries, not their feelings in response to them.

Having a partner to join you in the satisfaction of leaving is the best part. My wife and I have a little ritual where, after a few hours during any given event, we reserve the right to walk up to each other, smile and embrace and ask, well, did we do it?

And then the other person will raise their hand, give a high five and say, we did it.

Then we leave. No questions asked. The team has made a decision and now it’s time go. Period.

Doesn’t that sound deeply satisfying? If you’re the kind of person who regrets staying at everything too long, merely floating through experiences driven by external forces, it’s time to maximize control of your life.

Notice when you surrender your future out of guilt, fear, unworthiness or ambivalence. Practice setting air tight boundaries and sticking to them, even if you need a partner for validation and accountability.

Otherwise that undertow will carry you out to sea.

Has someone usurped your control, or have you given it away?

You have to do whatever it takes to become who you are

Being ourselves is important.

We now live in a world that places a considerable burden on each of us as individuals to come up with some unique self to be and rewards us accordingly.

For the most part, that’s a useful thing. But at a certain point, that pressure of individuality can become an impediment to our growth. If we’re holding onto that identity ship with our fingernails, unable to let go and iterate into the next iteration of ourselves, then we can’t evolve into what we might become.

Switching careers is a common way people do this. It invites them to transcend the limits of their individuality.

My transition from all the time entrepreneur to full time employee comes to mind. Looking back, it’s not that that version of myself wasn’t working anymore, it’s that there was a newer, healthier, more robust, more valuable version of myself that needed to emerge, but there was simply no space for that process to occur.

Psychological dislocation was needed. Even if the process was uncomfortable and foreign to me, it had to be done.

My mentor told me that when you’re being called to something different, the urge to hang on is really strong. And the tendency to try and negotiate a deal, to replace one process for another, is seductive. When the only real solution is to let go of any process at all.

In short, you have to do whatever it takes to become who you are. Otherwise you won’t contribute to this world at your most meaningful level.

What identity are you gripping too tightly? Which part of you no longer needs to be the heart of you?

You could let go of everything that you’ve tried and built and accomplished, except the person you’ve become, and used that to fuel yourself to your next stage of evolution.

Look, part of our growth as humans is the willingness to move and transform to wherever that process of change takes us, without letting the fear of what we’re leaving behind prevent us from evolving into something new.

By all means, be yourself, but don’t be afraid to transcend the limits of your individuality. 

What if within you was a version of yourself waiting to be realized?

A most fascinating and illuminating adventure

There was a new guy at our office a few years ago, back when people still went to offices.

In our first interaction, he noticed my nametag and thanked me for wearing it, as he had about forty new coworkers to meet that day.

This is a common interaction in a group setting. People will assume my nametag is worn specifically to help them feel more welcome.

Which is isn’t untrue, however, once we get to the second or third or fourth day, people quickly discover that it’s not just for them. The nametag is not an isolated incident, there is clearly some story behind it, and by god, they’re going to find out what it is.

Back to the new guy at my office.

In our third or fourth interaction, his response evolved. Well, I’m guessing this nametag is like, your thing, huh?

And I replied, yeah, it never comes off.

He furrowed his brow, shifted his posture and asked, well then why don’t you just get them embroidered on your shirt?

I answered, yeah, the process of hand writing every nametag is important to me. It puts a little bit of humanity in each one.

He then asked, do you write a new one each morning?

No, they’re batched a dozen or so at a time, I said.

Then his eyes lit up and he argued, ah ha! But then you’re not really connecting with yourself each day.

And my response was, yeah, but myself is boring. Connecting with you is more interesting.

These small interactions are priceless to me. After twenty years and tens of thousands of conversations just like it, boredom still hasn’t set in.

Because it’s such a window into human behavior, personal motivation, group dynamics and interpersonal identity.

I’ve always said that my nametag is an inkblot test, both for self and other.

What social experiment could you run for the next thirty days?

High impact plus low downside

Happiness is overrated in the macro and underrated in the micro.

Because on a major scale, there are so many things in this life more important than being happy.

Happiness isn’t the target, it’s what we get for hitting it.

Personally, my target it fulfillment. Which comes from making meaning in line with my values. If that is intentionally achieved, my incidental reward is happiness.

On a minor scale, there are very few things more important than being happy.

Life is hard, and we do what we have to do, hour by hour, to survive.

One way to personify this is to consider the list of all those small and simple adjustments, additions and subtractions that have a disproportionate effect on overall happiness.

Like lowering the volume on my alarm clock so waking up in the morning is gentler and more gradual. Or pruning the excessive items from my keychain so it’s less awkward in my pocket. Or switching over to dark mode on my computer so the default color is softer on my eyes. Or keeping a pair of warm, cozy clogs at my office for when my commute shoes are wet and gross.

Or playing relaxing music while pooping to help ease my bathroom experience. Or turning on the inbox category tabs in my email so it’s seamless to delete junk. Or waiting sixty seconds after getting off the subway to let hundreds of frantic people rush past me so my walk up the stairs is safer and slower.

Each of these tools and moments are little things with high impact and low downside. They bring a disproportionate amount of happiness.

What things are on your list? How often will you permit yourself to have them?

It’s worth noticing, celebrating and ritualizing. We live in a world that mostly a major abstraction, riddled with a million vibrating variables we can’t control.

Any parcel of control and joy we can wrestle from the chaos is not an insignificant investment. 

Are you immersing yourself in small, personal pleasures whenever you like?

Saved from the endless and fruitless struggle to understand

Anyone can be mindful if things are going well. Meditating on a mountaintop doesn’t take a ton of skill.

The real question is, what is your default response to life’s difficult moments?

Stoic philosophers promote a life in harmony within the universe, over which one has no direct control. Frankl later coined a term for this called response flexibility. His research found that between the stimulus and response, there is a space, and in that space lies our freedom and power to choose our response.

Thinking back to several of my own low moments, here are some strategies that have been useful for me.

First, instead of demanding perfection, we apply resilience by having compassion for ourselves. Taking the hit, absorbing the energy, and reminding ourselves that whatever happened isn’t personal, permanent or pervasive.

Like when my company fired our entire department out of nowhere. That night on the commute home, the story echoing inside my head was, listen, your worthiness is solid, you are a welcome presence who creates value, and since you’re great, you can be great anywhere.

Second, instead of trying to control things, we make a plan for dealing with unexpected outcomes. Accepting small and sudden change, while still taking control of our life and finding alternative means, like water flowing around a rock.

Like when the power went out on our entire block. After ten minutes, we hopped in the car, made our way to the nearest coffee shop, flipped open our laptops and got back to work.

Third, instead of regretting our decisions, we do whatever we can to improve our circumstances. Staying future focused, optimizing whatever is already propelling us ahead, and trusting that the right path is the one we take.

Like when my first job out of college as a bartender fizzled after six weeks. My dad told me to take the day off and celebrate, then hit the ground running the very next morning and darken people’s doorsteps into somebody hired me again.

Fourth, instead of screaming up at the skies and asking why the universe is so bloody unfair, we take life giving action and keep moving our story forward.

Like when that client stiffed me for three grand despite multiple efforts to collect the money, and then disappeared off the face of the earth. My mentor reminded me that it’s part of being in business, a rite of passage for all entrepreneurs, and that the best thing to do was to raise my fee and go find three new clients who actually valued my work.

These four moments are response flexibility in action. And just like physical flexibility, say, doing the splits or touching your head to your knew, it takes practice and it can be quite frustrating.

But it’s certainly a better use of our energy than our endless and fruitless struggle to understand why difficult things happen to us.

Remember, the mysteries of this world can’t be resolved by our sheer desire to resolve them, but we can certainly lessen our suffering by shifting the way we talk to ourselves when they happen.

What is your default response to life’s difficult moments?

Opening our hearts to absorb new streams of living eater

Time can be the great thinner of things.

Especially when it comes to our cherished habits and beliefs. Because the older we get, and the smaller our ego and pride get, the more we engage our capacity to outgrow what’s no longer working for us.

And this process doesn’t have to be painstaking. It’s certainly a grieving process, as any change is. But the thinning is less about renouncing and quitting and more about surrendering and shedding.

It’s this organic, elegant, natural process. Over time, these things we used to hold so dear, these pegs we hung our identity hats on, they’re simply left behind.

And the best part is, there’s no need for hard feelings towards any particular habit or belief. We accept they’ve become less interesting to us, and get on with our lives.

Thinking back to my own beliefs, my own coveted opinions about myself and this world, it’s borderline embarrassing about what used to pass for important to me. Makes me want find anyone who knew me prior to age thirty and send them an apology fruit basket.

Still, there’s no use beating myself up. Because such is the nature of time. It slowly wrings the wrongness out of us, opening our hearts to absorb new streams of living water, quenching our newly evolved thirst.

These forces of nature compel us loosen our hold on that which is unhealthy and set the stage for real change.

It’s really quite beautiful. We discover that evolving isn’t about being some perfectly consistent living realization of our values and beliefs every goddamn minute of the day, it’s about our ability to shed our old beliefs and accept new paradigms and surrender to who we are becoming.

As the mystics say, we must die to our old ways, we must come to the end of self before we begin to live.

Do you know when your reality is outgrowing your current strategy for navigating it?

If you’re threat, you’ll always be a target for them

Sorkin’s monologue at the end of the most successful baseball movie in history makes a powerful point about evolution:

Every time you start threatening the way that people do things, every time that happens, whether it’s a government, a way of doing business, whatever, the people who are holding the reins, they have their hands on the switch, they go batshit crazy.

It’s tribalism at its most human. Because people within power structures, from ten people to ten thousand people, will do whatever it takes to keep the spirits happy, keep the tribe’s nest warm and safe and show allegiance to the clan.

The problem with this very human tendency is, eventually, organizations and the people within them become trapped by their own limited horizons. They start working ideologically instead of pragmatically, and they become entrenched. Unable to see views outside of their own.

And so, it’s no surprise that when some hotshot rebel comes along with their fancy and fresh ideas, some rogue nation who attempts to abandon their allegiance to these powers, it threatens the organization’s way of life. Calling onto their carpet their former understanding of survival.

Brand writes about this evolution from the addict’s perspective, but it’s fitting in the context of a larger group:

Your old way of life is with you still like a worn down coin in your pocket that you toy with from time to time. Like a madman you sometimes countenance going back, back into the burning past to snatch at some scorched pleasure.

Point being, all of us must address the degree to which our ideas are fringes and tassels to the institutions into which we are born.

If we are in denial about our own tribalism, then we become prone to being manipulated by institutional propaganda.

But don’t forget, if you’re willing to flip the middle finger at the status quo in support of our collective evolution, be ready. If you decide to go against the grain, your choice will probably not be exalted.

And if you become a threat, you will always be a target for them.

Will you keep your head down and keep out of the line of fire, or take a bullet to the shoulder to elevate the game of the entire team?

The squeeze isn’t worth the juice

Have you ever had a conversation with a chronic interrupter?

It’s infuriating. They insist on correcting your grammar and fact checking your arguments and poking holes in your stories.

The problem is, they’re not exactly wrong, it’s just that the small amount their interruptions actually help is outweighed by the massive amount of energy they destroy.

Congratulations on sticking a pin the inconsistencies of my story, asshole, but now you’ve taken the wind out of my sails, killed my momentum and made me want to abandon the conversation.

This interpersonal quirk is a perfect microcosm for how businesses give their mistakes way too much power in their lives.

Within most organizations, employees will hypnotize themselves with all these things, and they end up like a dog with a bone. Not unlike the chronic interrupter, companies are persistently insistent and unable to let imperfections go.

Not that the details aren’t important, but when you’re working over every last facet within an inch of its life, you start losing the plot. You allow a lot of small things to overwhelm a few really big things. The squeeze isn’t worth the juice.

Edelstein, the famous movie critic, summarized this aptly in his latest review:

Some of the film’s liberties are an injustice, but most are harmless, and overall, one hundred small things wrong barely matter when there are one or two big things right.

This is the premise more businesspeople need to understand. If you’re doing the right things, it doesn’t matter if you’re doing things right.

The best thing we can do for ourselves, and our companies, is to allow the imperfections and failures as a normal part of the process of running a business.

Remember, not only is everything easier when you’re not afraid of making mistakes, but also when you’re not obsessed with dwelling on those mistakes.

Focus on the big wins, and the small losses won’t matter. 

Are you celebrating hitting one or two walk off home runs, or whining about hitting a hundred foul balls?

Coming to terms with people and all their weird byways

The opposite of judgment isn’t compassion, it’s curiosity.

This is our natural human instinct. We are the only species capable of asking the question of why. And that question leads us to discover what lies underneath and beyond the obvious.

Specifically, in the interpersonal realm. Only through curiosity can we embrace other people by the whole of who they are, rather than judge them based on a few isolated incidents of what they say and do.

Reminds me of a childhood friend, whom my other childhood friends have always thought of as eccentric. Probably because he’s an artist who dresses strangely, waxes poetic about esoteric subjects and performs in independent movies.

But in my opinion, he’s a fascinating, insightful and enjoyable person to talk to. Even if there is a smidge of eccentricity that’s unsettling at the start of the conversation, staying with that feeling typically leads somewhere interesting.

Sometimes you just have to stick around and see where it goes.

Masters writes about this beautifully in his book about bringing shadows out of the dark:

Instead of giving your fear higher walls, give it bigger pastures. Because the more curious we are about something, the less we will mind it being there.

And so, it’s a time thing. Training ourselves not to bail on people before they get interesting. Seeing if we can outlive whatever discomfort we have around human strangeness and following that vibe to a new destination.

Isn’t that more exciting and less objectifying that rifling off someone’s list of quirks as reasons to avoid talking to them?

Besides, think of all the times people told us that who or how we are was wrong or deviant or weird. Every one of those digs puts a little dent in our soul, until one day we look down and realize that the accumulation of those cuts has created a massive dissonance in the depth of our being.

This is what happens when curiosity takes a back seat to judgment. w

Are you scolding people to rein in their weird ideas, or giving them a platform to express them?

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