It’s Courageous Sunday! I’m here with your 4-part newsletter.

I just returned from a goal-setting retreat centered around Benjamin Hardy's work, Be Your Future Self Now. 

I expected to leave with a neat list of ambitious targets for 2026.

Instead, I left with a mirror.

Because before I could set new goals, I had to face an uncomfortable question: Why didn't I achieve the ones I set for 2025?

The answer wasn't lack of time. It wasn't a lack of resources. It wasn't bad luck.

It was fear.

Here's what I mean:

I didn't say no when I should have. Someone invited me to coffee, to an event, to a "quick call" and I said yes because I was afraid of disappointing them. Every yes to something misaligned was a no to my future self.

I didn't set hard limits. I let projects bleed past deadlines, let boundaries get pushed, let "just this once" become the norm, because holding the line felt uncomfortable.

I avoided hard conversations. There was a vendor relationship that wasn't working. I knew it. They knew it. But instead of raising the floor and demanding a higher standard, I tolerated mediocrity because confrontation felt risky.

Every one of those moments was driven by fear.

Fear was as disguised as being "nice", “reasonable” and “flexible.”

Not dramatic fear. Not obvious fear. Just the quiet, corrosive anticipation of an unwanted experience, someone being upset with me, a relationship getting awkward, a conversation going poorly.

That's all fear is: the anticipation of an unwanted experience or outcome.

All these things came at a cost, of time, energy, attention and money, that weren’t allocated towards my future self.

This is why the author, podcaster, and angel investor Timothy Ferris does quarterly fear-setting exercises. I highly recommend checking out his 13 minute Ted Talk where he shares his exact strategies.

The moral of the story is: I played to my current self's comfort level instead of my future self's capability due to fear. Full stop.

There’s simply no way around it. Becoming our future selves requires courage. Not just the courage to dream bigger, but the courage to disappoint people. The courage to hold standards. The courage to say no. The courage to have the conversation you've been avoiding.

Your future self isn't built on the goals you set.

It's built on the fear you’re willing to face.

As you look back on 2025 and ahead to 2026, and take time to actually consider

In what ways did fear impact your goals in 2025? 

Think about the goals you didn't hit, the boundaries you didn't set, the conversations you didn't have. Where were you avoiding the anticipation of an unwanted experience? What did that avoidance actually cost you? Don’t beat yourself up. Use this as leverage. 2026 is a new year. You have new information and resources to help make it your best year ever.

Where is fear most likely to stop you in 2026?

Your future self is waiting for you to show up at full capability, not someday, but now. What's the fear standing in the way? What's the unwanted experience you're anticipating that's keeping you playing small? Name it. Write it down. Take the smallest action towards it now.

That’s it for today.

Stay courageous!

— Jonathan