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Small Gigs, Big Wins: Rebuilding Confidence (and Cash) One Step at a Time

Inside this issue

• Side hustle vs. Freelancing: Where (and How) to Start
• How to Showcase Hustles and Freelance Work
• Time to Sprint: Brainstorm 3 Side Hustle/Freelance Ideas
• Weird/ unexpected side hustles
• The Last Laugh: When dad puts you to work
• But before we get to all that, here’s what’s…

On My Mind

The first paycheck after a career gap isn’t always a 9-to-5 salary. And that’s not failure… it’s freedom.

I’ve used side hustles and freelancing as my personal sandbox. They became a low-pressure place to test new ideas, practice the things I enjoy doing, and earn a bit, or even a lot, along the way. I found it liberating to set my own schedule and create new opportunities for myself, especially after being away from traditional work.

Side hustles let me try out new projects, discover what energizes me, and build my skills through small wins. Freelancing helped me put my strengths to work for clients who valued what I had to offer, all at a pace that fit my real life.

Here’s what I learned: gigs aren’t detours, they’re bridges. Every small win, every client, and every “I did that” moment helped me rebuild my portfolio, boost my confidence, and open up new possibilities. Sometimes the best next step is the one you create for yourself.

Side Hustle vs. Freelancing: Where (and How) to Start

Why it Matters

This isn’t just about cash; it’s also about traction. Picking the right path helps you build momentum when time, energy, and confidence are limited.

What to Pick

When choosing a side hustle or freelance path, start with what you enjoy. If you only have a handful of kid-free hours per week, spend them on something that feels playful or gives you energy, not extra stress.

Side hustles: Think flexible, passion-driven projects like stuff you want to explore, hobbies you enjoy, curiosities that energize you. Baking, tutoring, coaching, crafting, reselling kids’ clothes… if it’s fun and fits you, it works.

Freelancing: Use your veteran skills for someone else’s gain on your terms. Maybe it’s writing, consulting, web design, or even tech support. Tap past work experience and market it to neighbors, friends, or on platforms like Upwork or Fiverr.

How to Start

Follow these five steps to get started today.

1. Pick Your Fit: Ask, "If I only had 2 hours this week, what gig would I genuinely look forward to?"
2. Get Specific: Write down one service or product you can offer right now (no endless research, just a first draft).
3. Name Your Price: Decide what your time or product is worth. Start simple, even if it feels low.
4. Get Visible: Tell your immediate network (“I’m offering this!”) or post on social/LinkedIn. For freelancing, list your service on 1-2 free platforms or offer it directly to people you already know.
5. Take the First Step: Schedule one real session, delivery, or meeting. The goal is action, not perfection.

Remember: Progress beats perfect. Any first step, however small, is better than ideas stuck in your head.

How to Showcase Hustles and Freelance Work

Why it Works

Hiring managers care about proof of skills, not just job titles. Your projects, clients, or even micro-businesses can count as career currency.

How to Showcase

• Add a “Freelance + Projects” section on your resume.
• Write bullets the same way you’d list a job: action verb + outcome.
  • Example: “Developed social media strategy for small business, boosting follower growth by 30% in 2 months.”
• On LinkedIn:
  • Add your services to your profile
  • Post once about your gig (yes, it’s nerve-wracking, but it signals you’re back in action).

Pro Move

Don’t downplay small hustles. A weekend tutoring business demonstrates real leadership, initiative, and marketable skill.

Time to Sprint: Brainstorm 3 Side Hustle/Freelance Ideas

Why it Matters

Action > theory. Getting three ideas on paper flips you from thinking about “someday” to seeing “this week” opportunities. Even if they go nowhere, it builds creative momentum.

What to Do Right Now

• Minutes 0–5: Write one skills-based idea (something you’re already good at like tutoring, design, writing, tech).
• Minutes 5–10: Write one hobby-based idea (something you enjoy like cooking, fitness, crafts, photography).
• Minutes 10–15: Write one service-based idea (something simple like dog walking, handyman work, driving, helping local businesses).
• Bonus (next 10 minutes): Pick the most realistic one. Circle it. Name your price. Tell someone about it. That’s your experimental “next step” gig.

Your Move

What’s the weirdest or most unexpected side hustle you’ve ever tried (or thought about trying)? Hit reply and let me know. I read every response.

The Last Laugh

When dad puts you to work…