“Hopefully Soon" Is Killing Your Dreams: How to Start When Life Feels Too Messy

 

This week's article is a common thread I enjoy writing about: "How to simply start!" It stemmed from a recent conversation I had with someone dear to me. The talk started with laughter, little life updates, and that warm feeling you get when you're with someone you love.

So somewhere between her telling me about work chaos and a hilarious puppy mishap, I asked what felt like an innocent question:

"Hey… whatever happened to that side project you were excited about?"

There was a pause, just long enough for my gut to realize something deeper had been touched. Then she exhaled and said, almost casually:

"I don't want to make a fool of myself. And besides, life is hectic right now. Hopefully soon."

As she said it, she laughed and gestured at the half-unpacked boxes and messy desk behind her; they'd just moved. The visible chaos became Exhibit A in the case against starting anything new.

My smile stayed on my face, but inside, it hurt to hear.

Here was someone smart, creative, kind, and a person whose talent I would bet money on, quietly telling me she'd rather abandon something meaningful than risk looking foolish.

All I could say was:

"Start. Start messy. Start small. But start."

I don't know if I convinced her. But maybe it moved the needle one millimeter closer to "I'm doing this."  

Why Starting Feels So Hard (Even for Smart People)

Later that night, I captured the moment in my journal, Socratic-style, question, answer, follow-up question. Here I am, tinkering with Sumerian, launching AI systems, maintaining an old ERP, building web apps, running this blog, juggling a small circus of "Why did I say yes to all this?" projects… and yet some of the people I love most are still standing at the edge of the pool, toes in the water, unable to jump.

Different lives, different pressures, same standstill.

Why does it feel relatively easy for me to start new things and so brutally hard for others?

Here's the honest part: It wasn't always easy.

I used to live in that "hopefully soon" space, too:

• "Hopefully, soon I'll have more time."
• "Hopefully, soon I'll feel ready."
• "Hopefully, soon I'll know what I'm doing."

Spoiler: "Hopefully soon" is just a poetic way of saying "Not today."

The difference now isn't that I'm braver or more disciplined by nature. It's that, over time, I've broken the fear often enough that my brain has updated its internal script.

The Seneca gap: imagination vs. reality

The Stoic philosopher Seneca nailed this almost two thousand years ago:

"There are more things, Lucilius, likely to frighten us than there are to crush us; we suffer more often in imagination than in reality."

When my friend said, "I don't want to make a fool of myself," what she really meant was: "In my mind, the pain of trying and failing feels bigger than the pain of never trying at all."

That's the quiet math most of us are doing without realizing it.

Here's the secret: I had to learn the hard way: The only way out is through action, not more thinking.

Every time I launch a new project now -whether it's an AI experiment, a web app, or a post like this- I still feel that little spike of "Who do you think you are?" It hasn't disappeared. It's just lost its authority.

Case in point: as I'm writing this, my mind is quietly whispering, "Don't write that! You're not a professional psychologist!" "Your writing style sounds like a robot mixed with a TV game show host!" I've learned how to ignore it and proceed because here's what actually happens when you start:

• The first version will be bad. That's okay. It's a start.
• You'll get comments, looks, and criticisms that resemble that voice in your mind. That's fine too, because you'll quickly realize it's not that big of a deal as you imagined.

We overestimate the social humiliation. We underestimate the cost of staying stuck.

The result is a particular flavor of paralysis you might recognize:

• You care deeply about something
• You think about it all the time
• You might even talk about it. Plan it. Outline it.
• But you don't start.

You're not lazy. You're not broken. You're trapped in that Seneca gap between imagination and reality. 

Enjoying the journey so far?
If you like deep dives into creative chaos, productivity under pressure, and nerdy lessons from real-life experiments, subscribe to get future posts delivered right to your inbox. Subscribe Now 

The "Hopefully Soon" Lie

"Hopefully soon" sounds gentle. Responsible, even. But it usually hides one of three stories:

1. "I need the perfect conditions first."
   When I'm less tired, less busy, more organized, more inspired… then I'll begin.
2. "I need to be a different person first." More disciplined, more confident, more skilled, less anxious.
3. "I don't trust myself to follow through." So I'd rather not start than disappoint myself again.

None of those things magically arrive. Conditions rarely become perfect. Confidence doesn't appear out of thin air. And you can't rebuild trust in yourself without a track record of actually doing things.

"Hopefully soon" keeps you in the waiting room of your own life.

Tiny Starts: How to Move When You're Overwhelmed

If your brain is screaming "TOO MUCH," the answer is seldom "TRY HARDER." The answer is "MAKE IT SMALLER."

The 10-Minute Contract

Promise yourself 10 minutes, nothing more. When the timer ends, you can stop. Either you'll stop but feel integrity ("I showed up"), or you'll keep going because starting was the hardest part. Both are wins.

The "Ugly First Version" Rule

Make it a rule that the first version must be bad. This removes the notion that says, "I'm only allowed to start if I can also guarantee that it will be good."

You're allowed to start because you're human, curious, and alive. Quality is something we negotiate with reality over time.

One Question in the Journal

Try this Socratic prompt at the end of the day:

• "What tiny thing did I avoid today because I was afraid of looking foolish?"
• "What's the smallest version of that thing I could try tomorrow?"

Write the answers down. Don't try to be wise. Just be honest.

Shrink the Project Until It Fits Your Current Life

Side projects often live in fantasy land. Try this instead:

• Instead of "launch a YouTube channel" –>"film a 30-second short on my phone and publish it."
• From "build a full SaaS" –> "hack together a mock UI or POC and show it to one person."
• From "write a book" –> "write one scene that nobody has to see."

Your life might be chaotic right now. Don't build a project that requires a version of you that doesn't exist.

Build a tiny thing that fits the real you, in this real season. 

The Messy Room, Revisited

Going back to that conversation, my friend's explanation wasn't just about time or fear. It was woven into the environment: "Look at this place," she joked, panning her camera over the half-unpacked boxes. "I can't start anything serious like this."

And honestly? I understand. When your space is a mess, your brain feels like my browser with 43 tabs open and can't find the one playing music.

But here's the part I wish I'd said out loud:

No one whose opinion truly matters is keeping score of how quickly you unpack before you dare to write a poem, record a song, or build an app.

The people who care about you are just glad you're still here, still trying.
The rest are too busy worrying about their own mess.

Sometimes the most radical thing you can do is start despite the mess:

• Write the first paragraph with boxes still in the hallway
• Sketch the first idea on a sticky note taped to a dusty monitor
• Record the first episode with a laundry basket just out of frame

Future you will care deeply that you started.

The mess doesn't disqualify you. It makes you human.

Stay curious. Stay nerdy. Start anyway.

If you like deep dives into creative chaos, productivity under pressure, and nerdy lessons from real-life experiments, subscribe to get future posts delivered right to your inbox. Subscribe Now 

Note: This article details my personal journey with procrastination, doubt, and finding momentum. The strategies and insights are based on my own experiences and the research that guided me. They are not a one-size-fits-all solution or a substitute for professional advice. If you are facing significant challenges related to mental well-being, chronic stress, or making major life decisions, please seek guidance from a qualified professional. My only goal is to encourage that first small, sustainable step forward, whatever that looks like within the beautiful, complicated reality of your life.