Pursuing Fulfillment Over Finances

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Have you ever found yourself grinding endlessly, only to pause and think, “Is this really what I signed up for?” Maybe you started your business chasing freedom—only to end up feeling trapped by the very thing you built. It’s a common trap: the belief that working harder and enduring more pressure will eventually earn you the right to enjoy life after a big exit.

But as today’s guest discovered, you don’t need to wait 10 more years to start living. What you really need is a clearer why, a stronger structure, and the right people around you—people who understand your vision and support your growth.

Blake Denman is the president and founder of Rickety Roo, a remote agency specializing in SEO and paid search marketing. He’ll discuss his unconventional path into entrepreneurship, which was influenced by a personal injury, and the importance of designing your business and life around personal values, not just growth for growth’s sake. He also shares his time management strategies, how he uses AI for self-reflection, and his perspective on the mental load of entrepreneurship.

If you're an agency owner still doing everything—from ops to admin to taxes—you’ll relate to his story.

In this episode, we’ll discuss:

• Strategic hires that might results in your identity crisis.

• Designing your life before it designs you.

• Time audits, energy filters & the “$5K task” rule.

• Figuring out what you actually want.

• Do you thrive in chaos? Manufacture some healthy pressure.

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Sponsors and Resources

Wix: Today’s episode of the Smart Agency Masterclass is sponsored by Wix Studio, the all-in-one platform designed to help agencies scale without the headaches. With intuitive tools, robust native business solutions, and low maintenance, Wix Studio lets your team focus on what matters most—delivering exceptional value to your clients. Ready to take your agency to the next level? Visit wix.com/studio and discover how Wix Studio can transform your workflow, boost profits, and strengthen client relationships.

The Moment that Forced Him to Slow Down

Blake didn’t set out to build an agency. Like a lot of agency owners, he fell into it. What started as freelancing to pay the bills while he finished school and pursued a different career path took a hard left turn—literally—when a serious bike accident landed him with a traumatic brain injury.

That moment forced Blake to slow down. Rebuild. Rethink.

And when he got back into client work, he realized something: just because you can do it all doesn’t mean you should.

Like many agency owners, he hit the familiar ceiling of capacity. So he started hiring. First contractors. Then a coach in 2019. That’s when the game really changed.

The Pivot Point: Strategic Hires (and the Identity Crisis That Follows)

When you’ve built your agency from the ground up, letting go isn’t just hard—it can mess with your head.

One of the pivots that really made a difference in Blake’s agency was the strategic hires that required him to let go of some areas of the business. For instance, when he finally handed over operations. “I was like that John Travolta meme—just looking around wondering what to do with myself.”

And that’s the truth no one talks about: letting go of operations isn’t just a tactical decision. It’s emotional. You’ve tied your identity to being the guy who does everything. And suddenly… you're not.

That shift sparked something deeper—what Blake calls “identity paralysis.” Not a crisis, but a freeze. A moment of, “If I’m not the operator, who am I now?”

Spoiler: that question is the start of real CEO-level growth.

Designing Your Life (Before It Designs You)

Most agency owners plan every quarter like a military op: KPIs, OKRs, revenue targets.

But how many plan their life that way?

Blake started mapping his ideal year: the trips, the purchases, the experiences. Then he calculated what income he actually needed to live that life.

We’re mostly led to believe those goals are too far away, but the first time he did this he was just $1,500/month off.

So many agency owners think they need to sell their business to finally live the life they want. But often, you don’t need to sell—you just need to restructure. What if the business could serve your life now instead of being the thing you have to escape?

Time Audits, Energy Filters & the “$5K Task” Rule

Most people say they value their time but let it slip through their fingers, which is why you need a time tracking method that works for you.

After trying a few, Blake got a framework from one of his early coaches. He categorizes his weekly tasks into four buckets: $5, $50, $500, and $5,000/hour value.

If you think your time is worth $5,000 but the time audit shows its mostly spent in the $5 or $50 buckets, congrats—you’ve just diagnosed why your growth is stuck and your energy’s tanked. To his surprise, this is what happened to Blake, who was spending way more time than he thought on the $5 and $50 columns.

You don’t scale by doing more. You scale by doing less of the wrong things.

What Do You Actually Want?

If your agency isn't giving you time, freedom, and joy… what the hell are you building it for?

Blake now runs his agency with zero calls on Mondays. Focus time is blocked. The calendar is color-coded. And most importantly, the business doesn’t need him 60 hours a week to grow. He also has the whole team on Brain.fm, a tool that uses science-backed audio to get you in the zone faster.

Some would call that a lifestyle business, but so what? Lifestyle business can be extremely profitable too. Why not build your business around what you like and don’t like? People who  struggle for 20 years to then sell their agency find that after all their work they have maybe ten years left to do the things they want to do.

Lessons for the Owner-Operator Ready to Evolve

If you’re reading this and feeling that twinge—that mix of burnout and “I want more” clarity—take these cues from Blake:

-Let go of the identity that your agency is you. -Map your ideal life, then build your business to fund it. -Hire for elevation, not just delegation. -Your value isn’t in the tasks you do. It’s in the vision you hold.

From the Hustle Hamster Wheel to the Hedonic Treadmill

You want the 8-figure agency, right? So did Blake.

Until he realized that every time he hit a new goal, he’d feel good for a week… maybe five days. Then it was back to baseline. This is what’s called the Hedonic Treadmill—and agency owners live on it without realizing it.

We chase growth for growth’s sake. Or worse, for external validation—from peers, clients, even family.

Blake stopped to think about what was next after he had the money. Was he supposed to save it? Spend it? Did he even need that much? Define what you want your life to look like, and build your agency to support that. Don’t fall into the trap of chasing growth for validation more than for yourself.

If you let go of the idea of just hitting a number, surround yourself with the best team and clients, and set your priorities, you’ll be able to go after what you really want and live your best life.

Agency Owners & the Calm in the Chaos

Most agency owners have had the type of upbringing that’s them great under pressure. Calm in chaos. Laser-focused when everything’s on fire.

Of course, this can also become a trap if you start creating chaos just to feel normal. For instance, you may seek pressure to push you into action.

In his case, after years of needing the chaos, Blake turned to Claude to figure out a way to manufacture chaos without the disastrous consequences.

His AI coach creates a “painful penalty” for missing a goal. For instance, donate $1,000 to a political group you can’t stand if you miss a revenue target. That’ll light a fire.

Point is: for some people motivation isn’t just about dreaming big. If you need some added pressure to get working engineer consequences that make staying small more painful than pushing forward.

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