Is This Really That Hard… Or Are You Just Guessing?
I used to stare at projects thinking, “There’s no way I can do that.” Until one day, someone said something that changed everything:
“The only way to find out if the work is simple or doable… is to do it.”
So I did.
And you know what? 7 out of 10 times, the task wasn’t just doable—it was easier than I’d built up in my head.
Whether you’re a first-time entrepreneur, a mid-level professional tackling your first major leadership role, or someone switching industries, overthinking is costing you momentum. You’re Googling: • “Is project management hard to learn?” • “How to know if I’m qualified for a leadership position?” • “Can I run a business without experience?”
If that’s you, this post is your sign to stop asking and start testing.
Here’s the 3-step truth I discovered: 1. Start before you’re ready. You’ll never feel ready, and “ready” is often a disguise for fear. 2. Break it down. What looks hard in whole often becomes manageable in parts. 3. Reframe failure. It’s not failure. It’s data. Data you can only get by doing.
When I transitioned from banking operations to leading an entire nonprofit’s financial strategy, I didn’t know every answer. But by diving in, asking better questions, and learning as I went, we improved operational efficiency by 38% in under 6 months.
If you’re someone who… • Is launching something new (career, role, idea) • Wants to grow as a leader but feels stuck • Overthinks and second-guesses their own capability
Then this is for you.
In the next 24 hours, pick one thing you’ve been putting off—big or small. Don’t plan it. Start it. See if it’s actually hard… or just unfamiliar.
Trust this: You’ll never know what’s doable until you do it.
Let me know what you choose—I’ll cheer you on. Or better yet, share your first 3 steps in the comments to inspire someone else.
♻️ I hope you found this valuable, please share with your network.
Matt Gillis
Is This Really That Hard… Or Are You Just Guessing?
I used to stare at projects thinking, “There’s no way I can do that.” Until one day, someone said something that changed everything:
“The only way to find out if the work is simple or doable… is to do it.”
So I did.
And you know what? 7 out of 10 times, the task wasn’t just doable—it was easier than I’d built up in my head.
Whether you’re a first-time entrepreneur, a mid-level professional tackling your first major leadership role, or someone switching industries, overthinking is costing you momentum. You’re Googling:
• “Is project management hard to learn?”
• “How to know if I’m qualified for a leadership position?”
• “Can I run a business without experience?”
If that’s you, this post is your sign to stop asking and start testing.
Here’s the 3-step truth I discovered:
1. Start before you’re ready. You’ll never feel ready, and “ready” is often a disguise for fear.
2. Break it down. What looks hard in whole often becomes manageable in parts.
3. Reframe failure. It’s not failure. It’s data. Data you can only get by doing.
When I transitioned from banking operations to leading an entire nonprofit’s financial strategy, I didn’t know every answer. But by diving in, asking better questions, and learning as I went, we improved operational efficiency by 38% in under 6 months.
If you’re someone who…
• Is launching something new (career, role, idea)
• Wants to grow as a leader but feels stuck
• Overthinks and second-guesses their own capability
Then this is for you.
In the next 24 hours, pick one thing you’ve been putting off—big or small. Don’t plan it. Start it. See if it’s actually hard… or just unfamiliar.
Trust this: You’ll never know what’s doable until you do it.
Let me know what you choose—I’ll cheer you on. Or better yet, share your first 3 steps in the comments to inspire someone else.
♻️ I hope you found this valuable, please share with your network.
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