Rumi was right.

Life is a balance between holding on and letting go.

Sometimes we need the courage to hold on.

Sometimes we need the courage to let go.

Sometimes we need the wisdom to tell which one we should choose.

Yes, our lives are impacted by our conditions…the families we’re born into, our sex, ethnicity, height, God-given gifts, etc.

But our lives are also determined by our decisions…what we eat, the profession we choose, who we associate with, how we spend our time, money and energy, etc.

Decisions shape our lives. They impact our relationships, careers, health, communities,, identities, pretty much everything.

Get one big decision right, and you set yourself up for many years to come.

Get one big decision wrong, and you spend years, sometimes decades, carrying weight that was never yours to carry.

Good decisions pay dividends. Bad decisions create debt.

Over the past 5 years I’ve spent a lot of time and energy thinking about this.

Here are three specific examples of how the courage to let go has shaped my life.

1. The City That Never Lived Up to Its Potential

In April of 2015, I moved to Oakland, CA.

I was a first time homeowner and was excited about life.

San Francisco’s tech-boom was in full-swing, and Oakland, just 20 mins away was benefitting from the spillover.

New events, venues, bars, restaurants, etc. were popping up left and right.

In case you’re not familiar with Oakland, it has a lot going for it:

It has excellent weather, geographic terrain, world class parks (like my favorite Joaquin Miller), a zoo, an airport, and a great food scene.

It has a beautiful, natural, saltwater lake, in the middle of the city.

It’s a port city, with the 5th busiest port in the US.

It has one of the most ethnically diverse populations of any city.

It was home to professional, championship winning teams in basketball, baseball and football.

I loved Oakland.

No, I hella loved Oakland. (IYKYK).

I acknowledged it had some shortcomings but focused on everything it could be.

I used to walk around thinking, "This is going to be one of the best cities in America. Just give it 5-10 years. It’s inevitable.”

But year after year, I watched the same patterns repeat. And get worse.

The potholes that never got fixed. The low standards that got lowered. The normalization of broken car windows when parking on the street in downtown. The corruption that everyone just accepted. The violent crime and homelessness that grew worse while politicians pointed fingers.

The feeling that incompetence, dysfunction and mediocrity weren’t just tolerated.

They were protected. Defended. Dare I say celebrated.

Can you name another city that’s had 10 police chiefs in 10 years?

Exactly. The dysfunction is undeniable.

Yet, I was in denial.

I kept making excuses.

“Every city has problems. If we just pay more in taxes things will get better. Maybe next year it will be different. Maybe I can be part of the change.”

But deep down, I knew the truth: I’d fallen in love with potential instead of reality. I was holding onto a vision of what Oakland could be instead of accepting what it actually was.

When In-N-Out, the Raiders, the A’s and the Warriors all decided it was time to leave, so did I.

It was time to let go.

I sold my place in January, 2024.

I’d had enough.

After 8 years 8 months, 21 days, I had the courage to let go.

3,186 days of denial.

I finally accepted the uncomfortable fact that: “if you only see the best in people, you’ll often miss the truth.”

You can't impose your standards on a place that has chosen different ones.
You can't elevate an environment that doesn't want to be elevated.
You can’t help people that don’t want to be helped.

After, I sold my place, I put my stuff in storage and moved to Latin America to learn Spanish and give myself the space to explore my entrepreneurial and creative ideas.

I achieved both goals and recently just moved into a new apartment in San Francisco.

As I've been unpacking my boxes, I came to the realization that most of the things I’d been paying to store, no longer serve me. I’m giving them away. It’s time for me to let go of them. They reflect a version of me who no longer exists. Most of my clothes, furniture, and kitchenware weren't intentional. They were accumulated, not curated. They reflected who I used to be, not who I'm becoming. The old me who accepted whatever came instead of choosing with purpose. The new me unapologetically sets higher standards that are aligned with the future I’m creating.

It’s time to put on Marie Kondo’s Tidying Up and part ways with them.

2. The Friendship That Never Was Mutual

Last year, I had to let go of a friendship; one I'd invested heavily in for over ten years.

It hurt a lot.

I gave it my best to someone I loved like a brother.

I knew for years—years—that I deserved better. But I didn't have the courage to stand up for myself. I allowed myself to listen to their words instead look at their actions. So I made excuses. I told myself that maybe I was expecting too much. I lowered my standards. I betrayed myself. I let fear prey on the threat of experiencing loneliness.

When it became impossible to ignore the truth any longer, I finally made the decision to let go.

It hurt. Deeply.

It hurt so much that it was hard for me to focus on my work.

Emotions would come up out of nowhere. In the middle of the day.

Anger. Disappointment. Disbelief. Frustration.

I felt it all.

I wasn't just losing a friend; I was losing the illusion of the friendship that I thought I had. I was forced to accept the reality that no matter how good of a friend you are to someone, people won’t necessarily treat you how you deserve to be treated.

It took intellectual courage to challenge my beliefs that not everyone operates from the Golden Rule that I was taught as a kid.

It got so bad that I hired a grief coach to help me process it.

Grieving is real. It’s messy. It hurts. It’s uncomfortable. It’s not linear.

One day you feel better and the next you feel worse.

She helped me lean into it.

It took courage to be vulnerable and open up.

It took courage to feel the emotional pain and not run from it.

I sat with it, reflected in and healed from it.

I made the right call. Their actions revealed it with 100% certainty.

Yes, I paid for it with loneliness. That was the price of letting go. And it's 100% worth paying.

I’m stronger, wiser and more discerning now.

I have bigger courage muscles now.

And since that event, the universe has brought new people into my life that have shown up for me in ways that I couldn’t have imagined.

3. The Community That No Longer Fit

Two days ago I submitted my request to cancel my membership in a mastermind group I've been part of for the last five years.

I’m grateful I joined the community. I got access to some good investments, made some genuine friendships, learned about things I otherwise wouldn’t have known.

It’s absolutely had a positive impact on my life.

But, at the same time, I have legitimate frustrations about leadership.

I no longer see the organization for the stated values on its website.

I see it for what it is, based on the actions leadership takes.

Once I realized I was more committed to the organization’s stated values than the leaders of the organization, my decision became clear.

I won’t try to fight it. I’ll accept it. It is what it is.

Yes, the community is “good enough” to justify staying in, but every hour I spend somewhere that's "good enough" is an hour I'm not spending somewhere that's "exactly right."

Every commitment I make out of obligation is a commitment I can't make out of alignment.

The courage to let go is really the courage to raise your standards.

It’ about having the courage to say:

This was good enough for who I was, but it's not good enough for who I'm becoming.

On February 17th, we’ll enter the Year of the Fire Horse.

It’s a remarkable event in the Chinese Zodiac. While the zodiac cycles every 12 years, the Fire Horse year appears just once every 60 years, making it especially rare.

The last time this occurred was 1966.

Right now, we're still in the Year of the Snake.

And snakes do something remarkable: they shed their skin. They physically cannot grow while wearing the old layer. What once protected them becomes a constraint. So they release it, leave it behind on the ground, translucent and empty, a ghost of who they used to be.

Here’s the point: you can’t run fast while carrying dead weight.

The snake must shed before the horse can sprint.

The Fire Horse represents unstoppable energy.

And I’m ready to gallop at full speed.

Are you?

Here's your reflection for the week:

What is ONE thing you've been holding onto that no longer serves who you're becoming? A habit. A belief. A possession. A place. A person. Name it. Write it down. Have the emotional courage to feel what comes up when you imagine releasing it.

Here's your challenge for the week:

Let go of ONE thing. It could be small: a piece of clothing, a contact in your phone, an account on social media you follow that no longer serves you. Or it could be big: the conversation you've been avoiding, the goodbye you've been postponing, the decision you've been delaying. Addition through subtraction. Make room for what's coming.

Be loyal to your future self, not your past self.

As always: Start where you are. Use what you have. Do what you can.

With courage,

Jonathan