She Was Ready to Grow, But Her Help Was Holding Her Back: A Real Conversation Every Entrepreneur Should Hear.
But like many solopreneurs, she hit a familiar wall: “I need help… but I don’t know who to trust to do the job right.”
The other day, I had a conversation with one of my clients—an ambitious, creative entrepreneur who’s been grinding hard, managing events, custom design orders, and juggling side jobs in between. She was at that stage where things were picking up, and fast. But like many solopreneurs, she hit a familiar wall: “I need help… but I don’t know who to trust to do the job right.”
Her daughter was pitching in, and her son too. But the real challenge came when she brought on a friend to help with design work. That’s when things started getting complicated.
The Hiring Dilemma: When Help Starts to Hurt
She explained how her friend (who was recovering from knee surgery) offered to design graduation stoles. At first, it was a blessing. Her friend was idle, and she had orders piling up. But when the orders picked up steam and prices started increasing (rush jobs, premium packaging, higher demand), so did her friend’s expectations.
“She started feeling like she should be getting more just because the prices were going up,” she told me.
Sound familiar?
What began as a good-faith arrangement turned into tension and confusion because nothing had been written down. No independent contractor agreement. No defined terms for compensation as volume or pricing increased. It was all verbal and all vague.
My First Piece of Advice? Always Be Hiring Like Starbucks
I asked her a simple question: “Have you ever walked into a Starbucks and noticed what the manager is doing?”
Most people don’t, but Starbucks managers are always interviewing. Even if the team looks full, they’re building a talent pipeline. Why? Because people leave. People move. People go through life. And as a business owner, you have to be ready before the problem shows up.
Lesson #1: Even if you don’t need help today, start meeting your future team now. Interview regularly. Build relationships before you need them. That way, when the demand spikes, you already have talent waiting in the wings.
Lesson #2: Protect Your Sanity. Document Everything
I told her, “You need independent contractor agreements, even with friends.”
Without a written agreement, expectations get blurry. Someone feels taken advantage of. Resentment creeps in. But with a contract, everything’s clear:
Base compensation
Upside opportunities (percentage of revenue, bonuses)
Who pays for what (materials, packaging, labor)
How decisions get made when prices or volume change
I shared how I structure similar relationships: when someone doesn’t have the upfront cash to pay me, I’ll charge a small fee, then tie the rest of my compensation to the revenue I help generate (on a case-by-case basis). That way, they’re not taking a big risk, but I’m still incentivized to help them win.
She instantly saw how that model could have avoided the tension with her friend.
Lesson #3: Incentivize Performance, Not Just Presence
I explained that if someone is helping her produce work—designs, packaging, pressing—then compensation should reflect contribution, not just hours worked.
She could pay a flat rate for basic design work plus a percentage of revenue from each item sold. And as materials or packaging costs go up (like switching from plastic to velvet bags), those costs should be factored in before splitting profits.
It clicked. She said, “That makes sense. I was doing more because she handled the design, but I was pressing, sourcing materials, delivering—and she still felt shortchanged.”
I told her, “It’s not your fault she didn’t see the long game. But now you know to set expectations from day one. And as you scale, consider offering performance bonuses or revenue shares to those who truly help move the business forward.”
Lesson #4: Your Time Is Your Most Valuable Asset. Guard It Ruthlessly
As the conversation wound down, we shifted gears to something just as critical: how she was managing her time.
She admitted mornings used to be structured because she had to get her daughter to school. But now that summer’s here, the discipline vanished. She was waking up late, missing calendar reminders, and not showing up for herself the way her business needed.
I told her flat out: “I time block my revenue-producing hours, and I’m unapologetic about it. Everyone around me—family, friends, clients—knows not to call or distract me during that time. That’s sacred. That’s what feeds the business.”
Lesson #4: Productivity isn’t about being busy. It’s about protecting the right activities on your calendar. You can’t scale if you don’t control your time.
Final Words: If You Want to Grow, You Have to Invest
At the end of the call, she said something that stuck with me:
“I think my success really is hinging on better organization and learning how to manage people better.”
She’s right.
As entrepreneurs, we want freedom. But freedom comes after systems. After delegation. After learning how to work on your business, not just in it.
And that means investing in help, in tools, in coaching, in yourself.
If someone can save you six months of trial and error… if someone can help you double your income or cut your labor in half… that’s not an expense. That’s a shortcut to success, and an invaluable investment.
So here's my challenge to you:
Don’t wait until you’re drowning to look for help.
Protect your business relationships with clear agreements.
Tie compensation to impact, not just hours.
Train your calendar to serve your goals.
And most of all, treat investment in yourself as mandatory, not optional.
That’s how you scale. That’s how you stop trading hours for dollars. And that’s how you build something worth handing off someday.
💼 Ready to Build the Business You Envision—with Systems, Strategy & the Right Support?
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