Hey everyone!

Whether it’s my coaching clients or people I interact with every day on LinkedIn, Reddit, or my online community, one of the biggest struggles people face when trying to start a side hustle or business is fear.

People are deathly afraid of stepping out of their comfort zone. They'll plan, research, think about, and even talk about what they're going to do, because that's safe.

Unfortunately, the comfort zone is where dreams go to die.

You can't build a successful side hustle or business without doing things you’re afraid of, like sharing your knowledge online, asking for the sale, and taking the time to learn new skills.

Small, repeated, daily acts of discomfort.

Here’s the thing. The fear never really goes away, but the more you practice overcoming it, the easier it becomes.

So, how do you build that courage muscle?

It’s not by making big, bold moves.

Don’t try to go from zero to 100. Instead, practice taking micro-actions that get you out of your comfort zone, just a little bit.

You can practice this through what I call The Courage Challenge.

Try one or two of the following activities per day this week in no particular order):

1. Ask for a discount at Starbucks (or anywhere).
2. Post a 30-second Instagram Reel or LinkedIn video introducing yourself.
3. Message a dream client or influencer and compliment their work.
4. Record yourself talking for 1 minute and post it — no overthinking.
5. Ask someone for feedback on your website, post, or offer
6. Join a new online community and make your first post.
7. Send a “cold” DM or email to someone you admire.
8. Share a personal story about a failure or a lesson learned.
9. Go live on Instagram, Facebook, or TikTok for 2 minutes.
10. Ask a friend or a stranger for a small favor (like help carrying something).
11. Pitch your service to a local business owner in person.
12. Attend a networking event or virtual meetup and introduce yourself first.
13. Offer a free audit or consultation to someone new.
14. Post something imperfect, like your messy desk, a blooper, or a rough draft.
15. Share your goals publicly (in a post, story, or group).
16. Ask for a testimonial or referral, even if it feels awkward.
17. Compliment a stranger.
18. Dance, sing, or do something silly on camera, and post it.
19. Tell someone “no” (to practice boundaries).
20. Apply for a gig or opportunity you think you’re not quite ready for.

Here are three bonus challenges 👇 😉

⭐️ Reply to this email at the end of the week, and let me know which challenges you tried and how they went!

⭐️ Join my Facebook Group, The 9-5 Escape Project!

⭐️ Jump on a free 30-minute call with me, and I'll help you figure out your next steps on your 9-5 escape!

It doesn't matter whether you succeed or fail. (In fact, you will fail at a few of them, and that's OK.) The important thing is to show up and do uncomfortable things. The more you do it, the easier it becomes!

And the more you grow, the faster you'll be living your dream life. The one with more freedom, purpose, and control over your time.

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Until next week,

Colin