If You Want to ‘Work Less, Earn More,’ Ask Yourself These Questions

Agency owners often get to a point where they become stuck. Maybe they’ve been growing for a while and they’ve hit a plateau. Maybe they’re still growing, but their day-to-day is out of control. Or as one of my clients said: “It’s hard to think about what you’ll cook for dinner when you’ve got a knife stuck in your leg.”

Founders usually start agencies because they’re good at the work. Maybe it was design, development, or strategy. Clients asked for more and more. You started hiring other people to help… and suddenly, you’ve got a business. The “accidental owner” is not an uncommon figure. 

But what do you do about it now? 

It starts by identifying your spot on the Agency Growth Style continuum: Do you lean towards running a Lifestyle agency (with above-market pay and a great quality of life)? Or are you trying to create an Equity agency, where the goal is to sell for a big payday?

If you want to sell your agency, you likely need to make some big changes. You’ll need to get out of sales, or managing everyone, or being the creative director for every decision. The sooner you start elevating current team members and hiring new people, you’re more likely to have an easier future transition, and higher odds of getting a better offer.

I also get clients who say, “Why would I sell? I would just go off and start a new agency.” For those lifestyle-oriented owners, my advice is this: Make sure you’re getting paid what you’re worth—or ideally more than you’re worth—to compensate for the risk of being a business owner. You don’t have to stop doing things you love doing; just make sure you reduce your day-to-day stress. 

But the “Lifestyle vs. Equity” continuum isn’t black and white. 

Most people are somewhere in the middle. They’re not 100% one way or the other, but it’s important to know which way you lean. If you want to work towards an exit, plan on several years of ramp-up to prepare the business, build succession planning, and make yourself as optional as possible. If you lean toward the lifestyle side of things, you can choose to be as “optional” as you want. 

How do you spend your day?

Once they know their growth goal, I ask new agency coaching clients how they spend their time. 

I want to know, on a day-to-day basis, “What do you love doing? What do you hate doing? What do you tolerate?” 

In agencies with multiple owners, each person will answer those questions separately. During my analysis, I compare who likes doing what, and look for ‘quick’ wins’ to get the disliked things off their plate. But I’m also looking for overlap—or a lack of overlap. 

For instance, I worked with an agency a few years ago where neither of the two owners liked sales. That’s okay but someone is going to have to do sales. It turned out that they disliked dealing with early-stage time-wasters. They didn’t like dealing with flakey people, but enjoyed doing later-stage consultation and closing conversations.  

I had a straightforward solution for them: Delegate initial screenings to a more junior team member, so that the owners only meet with pre-vetted prospects. Problem solved!

How did you spend a perfect day – five years from now?

I am a fan of working backwards from your goals. I’ll guide clients on creating what I call an Advance Retrospective—where you’re writing about your ideal future day as if it’s already happened, and then work to move closer. 

Consider looking five years into the future: “Today is December 31, <five years in the future>, and it’s a great day because…” 

Then keep going— write what happened in your ideal future, including the experience and outcomes you want. Then you can enlist your team to work out how to make it happen. For instance, maybe you wrote that you were on no client calls—but your team notes, “Well, right now you’re on half the client calls—so how can we help you shift that?” 

Your team wants to help‚ if only you ask them. But they also need to know where you want to go. 

When owners are unclear about what they want, it creates a ‘leadership vacuum’. The team steps in to fill the vacuum, but this can create new problems. And you won’t always get the results you want. 

That’s why I start with a top-down approach. You’ll find certain areas where you need to deconstruct the whole process—whether that’s your client onboarding process, your employee onboarding process, your sales process, or your internal strategy. When you work backwards from your goal, you can focus on your top priorities first.

What’s your version of ‘work less, earn more?’

It’s OK to change your mind. Sometimes, agency owners say they want to sell—but then we work together to make the agency more profitable. Now, they might not want to leave after all. And sometimes the opposite happens.

What’s the gap between where you are now and where you want to be? The more you can close the gap, the more options you’ll see. Things are less stressful when you have room to think.

Ultimately, the concept of “Work Less, Earn More” will be unique to you. But once you find your version, you can make it happen. Good luck!

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