Welcome back, friend! This episode meant a lot to me. We talked about delegating, hustle culture, burnout, hiring your first team member, and what it really takes to delegate well (hint: it’s not just sending a Loom and hoping for the best). Whether you’re a solopreneur or ready to grow your team, I think you’ll find some real encouragement here.
Why I Invited Anna on the Show
Anna Solo is a talented editorial and wedding photographer based in Portsmouth, New Hampshire. She has a background in photojournalism and TV production, and she made the rare decision to hire a full-time employee before it felt “safe”—and well before she felt “ready.”
Most creatives start with contractors or VAs. Anna took a different route, and in this episode, we talk about how and why that decision paid off, even when it felt like a risk.
Anti-Hustle and Redefining Balance
Anna and I are totally aligned on this: hustle culture is not the vibe.
She shared how she keeps routines in her life—even during busy seasons—like making time for coffee, reading, or movement. These aren’t luxuries, they’re necessities for mental health and sustainability. I couldn’t agree more. When I started my business, it was to have freedom and flexibility. But for a while, I didn’t feel like I had either. If I created a job for myself that felt stressful and rigid, what was the point?
Delegation became one of the most important tools to restore balance and joy in my own work. And it turns out it was essential for Anna, too.
How Delegating Helped Anna (and Me)
Anna reminded me that even when you’re anti-hustle, it’s hard to let go. There’s a deeply rooted belief that if you want something done right, you have to do it yourself. But that belief kept her—and honestly, kept me—from seeing the bigger picture.
She realized she couldn’t be excellent at everything. (Who can?) And even now, she sometimes forgets she can delegate because she was so used to doing it all.
The real shift? Letting go of control, allowing space for mistakes, and seeing delegation not as a loss—but as a path to growth.
Why She Hired a Full-Time Team Member
This part of the episode really stood out. Anna didn’t start with a VA. She hired Brittany—a photojournalist friend from college—as a full-time team member.
They’d second shot weddings together and worked seamlessly as a team. For a year, they talked about what it would look like to go all-in. It felt like a massive risk. Brittany was leaving a steady job. Anna was taking on a big financial commitment. But they knew it was the next right step.
Anna was stuck in maintenance mode—shooting, editing, emailing, managing clients. There wasn’t space to grow. And she knew she needed more than piecemeal help—she needed someone fully invested.
What Happened Next: The Learning Curve
I loved Anna’s honesty here: it got harder before it got easier.
There was a steep learning curve—for both of them. She had to train Brittany on editing style, workflow, client communication, even brand tone. It took time. More time than Anna expected. And yes, there was a little burnout.
But once they pushed through that season, everything began to shift. Their roles became clearer and their processes smoother. And that’s when the real growth started.
I’ve experienced the same in my business. You can’t just drop someone into your systems and expect magic. Relationships take intention. And delegation takes time to get right.
Tangible Wins from Delegating
With Brittany in place, Anna got time back. Real time.
She now has space to:
- Plan social media
- Blog consistently
- Network with planners and vendors
- Join industry organizations
- Refine client experience
Brittany handles albums, editing, and culling—and often does it better and faster than Anna did alone. I’ve seen this in my own business too. Delegation unlocks creativity and momentum in ways that solo hustle never could.
The Money Talk: How She Made It Work
Let’s talk real numbers.
Anna shared that:
- She lives in a dual-income household with no kids
- Her wedding bookings were predictable
- She chose to take a personal pay cut for over a year
That part might surprise you—but I related so much. When I hired my first full-time team member, I had savings from a good year and support from my husband. I was able to take a pay cut too, knowing it was an investment in the business.
Not everyone can do that. But if you’re considering hiring, here’s what I recommend:
- Be honest about your finances
- Build a cushion before you commit
- Know what runway you have and plan accordingly
Pricing and Growth
Interestingly, Anna didn’t raise her prices right away. She wanted to ensure the value was there first. Over time, as their systems improved and client experience became stronger, they naturally increased their rates.
Avoiding Micromanagement
We talked about one of the biggest mindset shifts: not micromanaging.
Anna said she reminds herself how she felt when someone hovered over her shoulder. And she wants her team to feel confident and trusted. Even when Brittany makes a mistake (and we all do!), they address it with grace and transparency.
I’ve had to learn this too. Leading with trust creates a healthy work environment—and often brings better results. Sometimes your team will find a better, more efficient way than you ever could. That’s a gift, not a threat.
If You’re on the Fence About Delegating…
If you’re feeling the burnout and wondering if delegation is worth it, here’s what Anna would say (and I agree):
You can’t do everything. And you shouldn’t do everything.
Start with the things you don’t enjoy or aren’t great at. Editing, bookkeeping, inbox management—whatever eats up your time and drains your creativity. Delegating those opens up time for strategy, rest, or higher-value work.
Anna reminded us that leaving room to breathe is also leaving room to grow.
Connect with Anna
Website: annasolo.com
Instagram: @annasolophotos
Want More Support Like This?
Check out past Dream Biz Podcast episodes by searching “delegating” in your podcast player. And if you loved this conversation, let me know over on Instagram @christijohnsoncreative or keep listening to more podcast episodes here!
