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Your Side Hustle Failed: How to Start Over

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Hello, my beautiful sisters,

Let’s talk about something that doesn’t get enough love in the hustle culture—failure.

You had an idea. You put in the work. You had high hopes. But somewhere along the way, things didn’t go as planned.

The sales didn’t come in, the audience didn’t grow, or you ran out of time and energy to keep pushing forward.

And now? You’re left wondering: “What’s next?”

💭 Should I try again?
💭 Am I even cut out for this?
💭 What if I fail again?

Sis, let me tell you this right now: Failure is not the end. It’s the lesson before your next success.

You are not starting from scratch—you are starting from experience. And today, we’re going to talk about how to rebuild, re-strategize, and come back stronger.


Why This Hurts So Much

First, let’s acknowledge something important: this is painful. When a side hustle fails, it can feel personal—like you failed, not just the business.

That’s because your hustle wasn’t just about making money. It was about:
Proving something to yourself—that you could do this.
Gaining freedom—so you didn’t have to depend on a job you don’t love.
Building a dream—because you knew you were meant for more.

So when it doesn’t work out, it stings. But, sis, this is not your final chapter. Let’s talk about how to move forward.


Step #1: Take an Honest Look at What Went Wrong

It’s easy to say “I failed” and move on, but the real growth comes when you ask:

📌 What worked? (Even if it was small, something went right!)
📌 What didn’t work? (Were there warning signs you ignored?)
📌 What could I do differently? (If you started over today, what would you change?)

Action Step: Grab a notebook and write down your reflections. This is not about self-blame—it’s about learning from what happened so you don’t repeat the same mistakes.


Step #2: Shift Your Mindset from Failure to Pivoting

Failure is a label people put on things that didn’t go as planned. But in reality? You’re just pivoting.

Many successful people failed before they made it big:
💡 Oprah was told she wasn’t fit for television.
💡 Steve Jobs got fired from Apple before coming back and revolutionizing the industry.
💡 Tyler Perry had many failed plays before he became the powerhouse he is today.

Action Step: Change the language you use. Instead of saying “I failed,” say “I learned.” Instead of “I lost,” say “I grew.” This is part of the process.


Step #3: Find the Strength in Your Setback

Your first business didn’t work. So what? Now you have something most people don’t—experience.

You know what it’s like to put yourself out there.
You know what it takes to build something from nothing.
You know the challenges, and now, you can prepare better.

Action Step: Identify one skill or lesson you gained from your last hustle that you can use in your next one.

Maybe you learned:
📌 How to market yourself
📌 How to manage money better
📌 How to deal with customers
📌 What NOT to do next time

Sis, you are walking away with more knowledge than you had before. Use it.


Step #4: Decide if You’re Restarting or Reinventing

Now, ask yourself:
➡️ Do you want to try the same hustle again, but with a new strategy?
➡️ Or do you want to start something entirely different?

There is no shame in shifting to a new path if that feels right for you. Sometimes, failure is just a sign that you were meant for something better.

Action Step: Make a decision—are you refining your old hustle or exploring a new one?


Step #5: Start Small and Build Smart

When you start over, don’t make the mistake of going all in too fast. Instead, build in a way that protects your time, money, and energy.

Here’s how:
📌 Validate Your Idea First—Before you spend money on branding or websites, test if people actually want what you’re offering.
📌 Start as a Side Hustle Again—Give it time to grow before quitting your job or investing too much.
📌 Learn from Experts—Find free or affordable courses to strengthen your skills.
📌 Automate and Simplify—Use tools that make running your hustle easier so you don’t burn out.

Action Step: Write down ONE small step you can take today to start fresh. Maybe it’s researching a new business idea, reaching out to a mentor, or sketching a new plan.


Image from the Black Girl Heal website article: Your Side Hustle Failed: How to Start Over
Credit: Canva

You Are Not Defeated, You Are Being Redirected

Sis, listen to me: This was not the end of your success story.

💖 You are still capable.
💖 You are still talented.
💖 You still have something valuable to offer the world.

This experience? It’s just part of your journey. Some of the most successful people failed before they found their breakthrough—and you are no different.

The only way you truly fail is if you quit for good. But I know you’re not about to do that.


Uplifting Call to Action: Your Comeback Starts Now

Sis, this is your moment. Not to dwell on what went wrong, but to take ownership of what comes next.

🌱 Decide on your next move. Will you refine your old idea or explore something brand new? Choose one small action that moves you forward today.

📝 Write down your next step. Whether it’s brainstorming new ideas, researching a skill, or reaching out to a mentor—commit to just one step.

💬 Share your comeback plan. Drop a comment and tell me: What’s the first thing you’ll do to restart? Let’s build each other up!

👑 Affirm this: “This is not the end. I am learning, growing, and moving forward.” Say it out loud. Say it until you believe it.

Your success story is still unfolding, sis. Now go take the first step. 🚀✨

Author

  • Shelia Huggins Photo for Black Girl Heal Blog

    Shelia Huggins is a 20+ year attorney who has helped clients with their business and personal legal challenges. She blogs at Black Girl Heal to provide insight and practical strategies for those seeking to heal the struggles of their wallets, mindsets, and lives. Known as "Ms Legalista" on YouTube, she is passionate about helping people find their path and achieve the personal success they've been looking for.

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