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Advanced Goal Setting

You’ve probably heard of SMART goals. Setting a goal by this methodology helps to prevent some common missteps. However, there’s a widely unknown precursor to goal setting that is critical for bigger changes. That precursor is a vision.

I start every initiative with a vision:

  • A marketing campaign
  • Hiring someone
  • Building a product
  • Fixing systems
  • Etc.

SMART goals establish “what” and “when.” Visions lay the foundation by providing “how” and “why.”

They provide a contextual picture of how the world is different and from that you extract objectives.

I write visions from the stance of the future. If I’m setting annual objectives for 2023, I write the vision from my desk on December 31, 2023:

“It’s the last day of the year. I’m really pleased with how things have unfolded…”

When you integrate this layer, you can achieve your SMART objectives, but still fail in your vision. That’s important because you’re not ticking boxes, you’re trying to effect change.

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Dragged Behind The Horse

I ran into someone at a conference who had just exited his agency. We had a conversation that lasted less than a minute. In that minute, it confirmed a perspective that I have about growth.

After I congratulated him on his exit, I asked him what it took to grow it to the point where he could sell it?

He said, “You know, it’s funny. I didn’t do anything. I never had any intention of growing, but we couldn’t not grow. Work was piling up and so I kept hiring to accommodate it.”

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Art History & Short Stories

I recently finished a short story that I wrote as a final paper for an early medieval art and architecture art history class. It’s about a veteran who continually travels to avoid nightmares from a traumatic event in the Iraq War. On a red-eye flight, a fellow passenger gives him an ancient pilgrimage flask and tells him that, if he can fill it with what it’s designed to hold, his nightmares will go away.

I’m taking an art history class for the same reason that I decided to submit a short story rather than an essay for the final. That reason is strengths development.

As the business operator, you’re in a place of leverage that impacts the arc of the entire business. Because of this, developing your natural advantages has an outsized impact.

One of my recommendations from Strengths Finder is to take a university level class at least once each year (Learner.) And creative writing is an application of several of my strengths (Focus, Strategic, Intellection.)

I don’t know that I’ll ever pull some insight about Dicoletian’s Palace into a business deal or if I’ll write a clever allegory that serves as a lead magnet. That would be great, however I see it more like lifting weights. It’s the exercise of gifts that has a broad effect outside of the gym. At a minimum, it makes me happier and that is a worthwhile end in itself.

This time each year I reflect on my strengths. Here are five good resources that I’ve used over the past many years:

Applying the information from any of these will make you more productive and happy.

Another ritual I do each year that follows strengths exploration is an annual reflection. Last December, I ran it as a group activity with other business owners on a Zoom call. Reflection is a powerful tool to learn and adapt and last year’s group reflection changed my entire year for the better.

This year I’m partnering with Patrick Pitman from the Easier Business Podcast to roll it back. If you’re interested in participating, give me a shout out over email and I’ll keep you in the loop as we firm up the dates and times.


Featured image is “View of the Peristyle” in 1764, engraving by Robert Adam of Diocletian’s palace in Split, Croatia. If you’re ever in Croatia, it’s a fascinating place with restaurants and shops nestled in an ancient retirement home / fortress for an emperor. Used under public domain.

Telling Your Business’s Fortunes

One of the things that frustrated me for a long time about the agency business model, was that it wasn’t very predictable. Consider a business with:

  • Custom, variable priced products (projects.)
  • The kind of customer impacting the price and amount.
  • Smaller quantities (sell tens not thousands every year.)

Because of these factors, the income of creative agencies paints a jagged line of peaks and valleys.

What can an income statement tell you in that environment? Sure, last month was terrible, but a whale can swim into your office tomorrow and triple your revenue for the next six months.

The result of this is that many agency owners have a hard time investing in the business. You’re bursting at the seams with work right up to the moment that you’re dead as disco.

As time passed though, I noticed something odd: we hit a ceiling in revenue. Despite my efforts, every year we’d come in within a range that spanned around $30,000.

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2022 Gratitude

I enjoy traveling by plane because it provides quiet time to think. When I left for Thailand last month, I used that time to journal about how my year had gone. For the business, it was a mixed year where most of my initiatives had failed. It was depressing. Frustrating.

Holding those failures in my mind, I asked myself what I was grateful for?

I’m grateful for:

  • The opportunity to learn.
  • The humility and empathy that failure provides. This is foundational in helping others.
  • The things that are working and provide for me and my employees.

I had dinner with several entrepreneurs last week. One of them had closed their business because they felt like it wasn’t going anywhere. Now, he’s a well paid employee at a corporation. He has the financial security that his business lacked, but is dissatisfied with his comfortable life and is looking for his next business.

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Why Less KPI’s Matter

For the past couple of years I’ve tracked our business on a spreadsheet that I call, “OSTRUTA: One Spreadsheet To Rule Them All.” Beyond being a fun reference to Lord of the Rings, the spreadsheet ended up with grandiose acronym because it’s big. I’ve been tracking metrics from all the different functions of the business. But as time has passed, I’ve realized that it’s not helpful.

The two big problems it poses are:

  1. It requires work to update. It’s not all on my shoulders, our PM updates our operational scores, but with all the competing priorities on my plate I can fall behind and update it after the fact.
  2. Because I’m busy, I often get it up-to-date and leap on to something else without thinking much about it. It becomes a scorecard for what has happened, but doesn’t add value from a decision making capacity. Which is its highest potential value.

Right now, I’m leaning it down, making it easier to report on, and increasing our reporting tempo.

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Guillotines As Growth Opportunities

I used to train Brazilian Jui Jitsu. I remember a grappling match I had in the gym where I was going back and forth with this guy, attacking and defending. At one point, he popped up on his feet and in response I transitioned to a double leg takedown. Immediately, he sunk in a guillotine choke. What had been give and take suddenly became me struggling not to get choked out. Afterwards, when we were resting, I asked him, “Hey, remember when I tried to take you down and you guillotined me? What was I doing where you were able to sink in that choke so deep?”

He thought about it for a second and then said, “Your head was down. It was like a neon sign that said, ‘guillotine here.””

At some threshold in my training, I started to learn more from grappling than from the formal instruction of classes. Sometimes, I’d be stuck with an opponent and I’d learn by using principles and hypothesis to test tactics to break through that wall. Other times, I’d get caught and ask my opponent what they saw, like with the guillotine.

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Ignorance in Horizontal Positioning

As a freelancer, I positioned within the first two years to focus exclusively on development for a kind of website using a content management system called, “Joomla.” This helped me to double my earnings and grow a small team. However, Joomla declined and our robust lead flow dwindled away to nothing.

I decided to try and fix things and really understand how the agency business model worked. I networked more with other agency owners, attended conferences, worked with coaches, and studied agencies.

One of the things I learned was that most agencies had no lead generation plan and many did well despite this. They subsisted on a low, but fairly consistent flow, of word of mouth / referrals.

This mystified me because we received almost no referrals, despite doing great work and having happy clients. All of our leads came through SEO and directory marketing.

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Knowing Your Levers

In the reality TV show, The Profit, entrepreneur Marcus Lemonis turns around small businesses in exchange for equity. It’s entrepreneur porn, where situations are dramatized, rough edges are obscured, and complex choices simplified. With that caveat, it’s still fun and useful to watch another entrepreneur make choices in 40 minute case studies.

One of Lemonis’s go-to tasks is to seek out, “the numbers.” As in, revenue, profit, and expenses for the business. Then he drills down looking for opportunity in products that are highly profitable or expenses that don’t provide much value to the business.

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Close Out

Every six weeks, I set objectives to work on for the business. I create a vision for the period, line out SMART goals, and add in some meta questions to consider over the period (like how to practice a specific strength.) At the bottom of the document is a section I complete at the end of the cycle, named “Close Out.”

Close Out is a self debrief where I answer questions about what worked, what didn’t, patterns, and pain points. It’s where past John meets future John to close the circle on our ambition.

Invariably, something changes after that debrief. The objectives have passed, successful or not, but their full benefit isn’t realized until I debrief them.

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