In my professional life, I’ve actively conditioned myself to tolerate and accept risks when necessary. Risk tolerance is something that can be learned and taught. But risk tolerance is fundamentally a contextual matter - two people with identical means and skills can have totally different reactions to the stressors risk presents.
There are people who will go skydiving but won’t ever, ever leave their stable corporate job that they hate because the alternatives terrify them. There are people like me who won’t jump out of a perfectly good plane, even at gunpoint, but feel totally comfortable entering work situations even with uncertain economic outcomes.
I’m generally confident and assertive, but my biggest regrets in life have come from situations where I failed to be either. In these moments I make a common mistake: when I weigh my choices, I invent additional possible negative outcomes that don’t actually exist.
Small, Safe Worlds
I have my insecurities. Most of them are artifacts of routine childhood slights, like being picked last for the pickup soccer games in fourth grade; I relive them every day as adult anxieties. You’d think after 30-something years I’d be seasoned enough to not be affected by these things. You’d be wrong.
When life presents us with possibilities and choices we view them through the lenses formed through our experiences over time. They shape the landscape in which we decide.
Ultimately these lenses distort reality into a funhouse mirror, tainting our judgment with shades of the past.
With negative experiences, we decline and avoid opportunities for connection, growth, and prosperity because we wish to avoid pain.
We preemptively discount ourselves because we’re afraid we’re not worth our asking price and that we’ll be exposed if we do.
We don’t ask for the promotion we earned. We don’t assert ourselves in situations where our boundaries are crossed. We don’t ask the single neighbor out for coffee. We don’t start that company. We don’t travel to exotic, unfamiliar places. We turn down invitations to make or grow relationships. We engage in safe, people-pleasing, small-ball behavior. We limit ourselves to a smaller, safer world filled with fewer possibilities and people. We retreat to our comfort zone.
Access to Possibility
Like our friend who makes the same mistakes because he or she can’t spot the warning signs, so too can we see that the friend who avoids opportunity does so for reasons that are absurd, childish, and mundane. Our own reasons for doing the same are equally weak, but they hide in our blind spots. Thus we carry on, carelessly closing off opportunity for a different, better, and richer world for ourselves every day.
And why? Because Mrs. Rutherford publicly humiliated us in front of our second grade class for having really shitty cursive handwriting. From that day onward we’ve spent our entire lives avoiding being the center of attention. We wonder why none of our ideas get picked up at work, why we don’t have the friends and relationships we want, and confine ourselves to gilded cages of our own making - all because of an overwrought childhood experience exercising its influence unchecked.
I worry about being liked and respected. Being an awkward, chubby, and nerdy kid made me an easy target for bullying. For a significant part of my childhood, I simply tried to avoid contact with people as best as I could and pursued my hobbies instead. I kept my circle of friends small. I avoided dating until I had women in college dropping atomic bomb-sized hints that they were interested in me. Asking customers for the order terrified me because I was worried my labor and products weren’t worth their true value. My primary social goal was to simply avoid embarrassment.
Change waited for me just around the corner.
During college I realized: I’m in control of what embarrasses me and what doesn’t. Embarrassment was my choice. Being lonely, unhappy, unsatisfied, slighted, and the entire spectrum of socially anxious behavior were outcomes I unconsciously chose all along.
So I made a promise: to reinvent myself as someone who doesn’t get stopped. Choice is my instrument. I made different ones. I’m twelve years in.
If you meet me in-person today, you won’t recognize the man I just described. I’m extroverted; I work the room; I speak in front of hundreds and thousands of people regularly; I assert my boundaries; and I ask for what I want, especially when it’s a big ask. I act with a degree of self-worth that was unavailable to me when I was nineteen years old.
I still get knots in my stomach when I don’t know anybody at a party and I have to mingle with strangers. I’m reluctant to reach out and form new friendships because I worry about looking like an incompetent manchild. I tense up when I’m about to send an email asking for a large order. There are lots of moments, every day and every week, when I fail to act with conviction; when I don’t ask for what I want; or when I fail to assert myself and my boundaries vigorously. I leave a breadcrumb trail of tiny, everyday regrets in my wake. But the upside is: I didn’t even have a wake before.
Like anything else worth doing, broadening our world and learning to say “yes” to the call of opportunity takes practice, repetition, and a generous helping of patience.
How to Get There
We view the “risk” in any given situation through the lenses of our past experience. In the realm of the interpersonal, I thumbed the “risky” side of the scale heavily because my lenses magnified the specter of embarrassment many times over. My imaginary threat often outweighed the real positive potential outcomes. I justified each act of self-disappointment with post-hoc rationalizations.
We all do this.
It’s when we realize that the threats aren’t real that we can make different, better choices. When we’re aware of how our past distorts our view of the present, we open ourselves up to possibility and opportunity.
The hard part is reconciling how we feel with what we should do. Our feelings are real sensations, but they aren’t reality itself. Our negative feelings are the machinery of the mind trying to protect us from aggravating the injuries of the past.
Every day I practice moving past how I feel and instead, learn to act in my own best interests. Do it often enough and it becomes automatic, unconscious, default behavior. Here’s how I do it:
“It’s just not a big deal.”
When I’m afraid to ask for what I want or to say “no” to a request I don’t want to entertain, this is what I remind myself.
If you conduct yourself with integrity there are very, very few situations where asking for anything or saying “no” will lessen other peoples’ opinions of you.
If someone asks you for $20 on the street you’d say “no” without thinking twice about it; so why feel differently when a friend asks you to help them out with a bill? It’s because you’re invested in the friendship and you worry, irrationally, that saying “no” will damage it. The truth is if your friendship is worth keeping then saying “no” has no impact.
Similarly, we don’t think less of the friend for asking in the first place. They needed help and turned to you.
It’s not a big deal they asked and not a big deal that you declined. Repeating this exercise allows us to stop seeing normal, everyday interactions as significant life or death decisions. It reduces the intensity of going about our daily lives. It deepens your power to choose your own boundaries, priorities, and preferences.
“You’ll be glad you did it.”
A phrase from my grandmother that has served me well over the years. When I’m afraid of putting myself in a situation where I feel vulnerable, I tell myself this and I move in that direction anyway.
Asking for an order, asking for a phone number, inviting people over for dinner, discussing an overdue raise with the boss, and millions of other situations that seemed risky in the past become opportunities instead.
When you ask for something you want, the worst that can happen is you’ll be told “no.” You’ll be in the same situation you’re in right now, but with certainty and satisfaction in knowing that you didn’t leave opportunity on the table.
The real power in doing this is the unlimited upside. While most people tremble at the thought of asking their boss for a raise, worried that the act of asking itself might result in a loss of face or favor, you can be the person who actually gets it. Maybe that customer will accept your face value price after all. Maybe that attractive co-worker really is interested in going out with you.
When you act despite your self-doubt and advance your best interests, you value yourself. You grow your access to opportunity. And you’ll be glad you did it either way. Each time you repeat this exercise you take a step closer towards being the person who takes shots on the goal.
Given enough practice, you can become the person who makes them.