Running a business means facing tough questions — and way too often, we face them alone.
Should I grow a team or stay solo?
How do I pick a niche when nothing feels like the one?
What kind of productized services actually sell?
Why do my clients disappear after paying a deposit?
For this month’s Happy Hour, we’re doing something a little different…
We collected real (anonymous) submissions from Barflies who are dealing with very real challenges in their business — and we’re bringing them to the group for live feedback, discussion, and support.
It’s a chance to hear how other agency owners are thinking through the same stuff you’re probably dealing with too — and share your own perspective along the way.
Join us for a collaborative session where we tackle some of the stickiest agency problems… together.
Questions We Tackled in This Call
- How to Choose a Niche (2min 20sec)
Emma got into web design because she loved building websites — but running a business has been a completely different challenge.
She’s spent years saying yes to whatever work comes her way (even if it’s not really what her business offers) because it’s hard to say no when someone wants to hand over money. She’s been hoping a niche would eventually reveal itself. But it hasn’t. The business side feels scattered, and with everything changing so fast, picking a clear direction feels risky. She’s stuck asking: Do I need a niche? And how do I choose one when nothing feels obvious? - Is Growing a Team Really Worth It? (23min 30sec)
Jordan runs a solo agency and is wrestling with the idea of growing a team.
He’s torn — because while building a team sounds like the next step, he’s not sure it’s what he really wants. He enjoys the creative work, and worries that growing would mean trading that in for project management and admin headaches.
And then there’s the money. He knows that hiring help would mean making less — at least for a while — and he’s unsure if the short-term sacrifice is worth the long-term gain. What would that financial dip look like in reality? And do people ever regret going the team route? - How Can You Market Your Agency When You Have a Full Time Job? (40min 40sec)
Chris has a full time job working 5 days a week (4 days in office with a 1-hour commute, and 1 day remote from home). That doesn’t leave him much time to work on his agency. He’s trying to get the word out about his services in his local area, but he’s tied up on his full-time job during working hours, which makes it hard to do any networking.
How can Chris get visibility locally if he only has limited time during non-standard working hours?
Here’s a look at some of the questions we’ll be tackling (depending on how many we can get to):
Emma got into web design because she loved building websites — but running a business has been a completely different challenge.
She’s spent years saying yes to whatever work comes her way (even if it’s not *really* what her business offers) because it’s hard to say no when someone wants to hand over money. She’s been hoping a niche would eventually reveal itself. But it hasn’t. The business side feels scattered, and with everything changing so fast, picking a clear direction feels risky. She’s stuck asking: *Do I need a niche? And how do I choose one when nothing feels obvious?*
Jordan runs a solo agency and is wrestling with the idea of growing a team.
He’s torn — because while building a team *sounds* like the next step, he’s not sure it’s what he really wants. He enjoys the creative work, and worries that growing would mean trading that in for project management and admin headaches.
And then there’s the money. He knows that hiring help would mean making less — at least for a while — and he’s unsure if the short-term sacrifice is worth the long-term gain. What would that financial dip look like in reality? And do people ever regret going the team route?
Alexa is trying to build a reliable bench of freelancers — but organizing it is a mess. She’s not sure how to keep track of who’s available, what they’re good at, and how much they charge so she can price, triage, and assign work easily. Her big question: What’s the best way to organize and manage a freelance database that actually works when you need it?
Morgan has built a thriving business by saying yes to everything — but now wants to scale without being the glue holding it all together. Over the years, they’ve offered everything from web design to newsletters, SEO, headshots, and marketing strategy — all tailored client-by-client. It’s working (over $10K in MRR!), but it’s hard to systemize when no two projects look the same. Morgan’s asking: How do you build systems and step back when your entire business is built on being a generalist?
Chris has a full time job working 5 days a week (4 days in office with a 1-hour commute, and 1 day remote from home). That doesn’t leave him much time to work on his agency. He’s trying to get the word out about his services in his local area, but he’s tied up on his full-time job during working hours, which makes it hard to do any networking.
How can Chris get visibility locally if he only has limited time during non-standard working hours?
Dana is exploring productized services, but she’s not sure what people actually want to buy. She’s considering things like “Get a brochure site in 48 hours” or “Flat-rate website audits,” but worries about putting in the effort to build packages that don’t sell. Her question: Which productized services actually work — and which ones are a waste of time?
Taylor’s biggest struggle is getting clients to follow through — with content and communication. Projects stall when clients drag their feet on delivering copy or disappear altogether after paying a deposit. Some jobs end up dragging on for months with no clear timeline. Taylor’s asking: How do you keep projects moving when clients won’t?