Simplicity Scales

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Simplicity Scales

One of the best pieces of business advice I've ever received came from a short snip from Author Dan Sullivan:

Before you can get to the next level, you must simplify.

I’ll admit this sounds like a stupid way to frame this edition but stick with me here, this will make sense, particularly with everything going on in the world.

We tend to associate “scale” with sophistication, with more moving parts, more complexity, more strategy layered on top of strategy. But the older I get, the larger our business has gotten, the more complex my personal life has become, the more I’ve seen it with clients and their businesses, the more I believe it is one of the most important financial principles you can internalize right now.

I'm writing this overlooking Central Park, about to head into an industry conference focused on AI, the aging financial advisor and the state of the wealth management industry. New York is the most complicated city in the world. It is expensive, loud, and remarkable. And yet the irony of being here is hard to ignore, because for every entrepreneur who came to this city with a dream, they started with something remarkably simple. The complexity came later. The simple idea came first.

Simplicity precedes scale. And I think right now, given everything happening with AI and the geopolitical environment of the last few years, it's the right moment to look hard at your financial life through that lens.

Here's the idea I want you to sit with this week: complexity is not just inefficiency. Complexity is risk.

We've spent the last few weeks talking about how AI is reshaping career risk in ways that are genuinely new. There's more uncertainty in careers than there has been in decades, but also, for the people positioned correctly, the potential that the economics of five people could land on one set of shoulders. Think about that for a second.

Risk has shifted. And that shift in itself is a form of complexity that most financial plans haven't caught up to yet.

Sundar Pichai, Google’s CEO, said recently about AI potentially being able to replace his role at Google with relative ease. At first glance it sounds absurd. But he runs one of the most sophisticated technology companies on earth that will have an agentic level beneath every single employee. It will know everything about the company inputs and outputs in a way a person cannot. It makes sense if you think about it.

So if risk has shifted even for someone in that seat, it has shifted for all of us.

Complexity makes it hard to see what you need to fix. Complexity takes your eyes off the ball. It’s like playing a game of whack a mole that you can’t seem to win.

This is all about transition. Whether you are working or not, this new age will force transitions. Think about it like this, if you are moving to a new house, you have to take time, whether you pay movers or not, to go through your stuff and figure out what you want to keep, throw out, donate, or sell. It’s a process of simplification that then begets the move.

So what does simplicity actually look like? The same four quadrants we talked about last week give us the right framework here.

On income, if you are a business owner or in the later stages of your career, your ability to generate income and translate it into your balance sheet is itself a risk. The question worth asking honestly is how many years of meaningful income generation you have left, and whether your financial plan reflects that reality. Five years looks very different than fifteen. If the answer makes you uncomfortable, that discomfort is a signal worth acting on, not ignoring.

On spending, what makes financial lives complicated from a spending perspective is obligations. Contractual ones are the most dangerous because they dictate what your future self can and cannot do with money. I'm not saying mortgages are bad or that car payments are inherently wrong. But every obligation is a constraint on future flexibility, and the more of them you carry, the more pressure points you create that you may not be able to see until something external forces the issue.

On investing, balance sheets can become cumbersome as they scale, and there is a tendency to believe that complexity is a sign of sophistication. Think about what Steve Jobs built at Apple: a handful of products, refined relentlessly over decades, sold to as many people as possible. Radical simplicity producing extraordinary scale. The most sophisticated minds in business history keep choosing simplicity, and that is not a coincidence. Our most successful clients in retirement choose this same motto. Anytime our business is at an inflection point, my instinct is always – is this simpler? Anytime we’re dealing with a complicated client case, the best answer is most certainly the one laced in simplicity.

On risk, this is where the idea cuts hard. If you are $500,000 light in your financial plan, that is a risk. If your income runway is shorter than your plan assumes, that is a risk. Complexity obscures gaps. It creates noise that makes it harder to see clearly where you actually are and where you are actually going.

Dave Ramsey built an empire teaching millions of Americans to pay off debt and eliminate fixed costs. It worked because it was simple, and because simplicity relentlessly applied eliminates pressure points before they break. His approach was designed for people trying to get out of trouble. If you're sitting with a few million dollars looking toward retirement or a business exit, the same principle applies at a different scale. The complexity you've accumulated along the way, the obligations, the sprawling balance sheet, the financial life that has grown faster than the strategy behind it, that complexity is the thing standing between where you are and where you want to go.

Engineering simplicity into your strategy right now is the prerequisite for the next level, whatever that looks like for you.

The question worth asking this week is this: where is complexity creating risk in your financial life that you haven't fully looked at yet?

If you don't know where to start, start with your obligations. List every contractual commitment you carry and ask honestly whether each one is moving you toward the next level or anchoring you to the last one.

That answer is worth finding before something else finds it for you.

If you’d like to talk through how this applies to your own financial life, you can learn more about our work at Fjell Capital here.

And if you found this edition useful, let me in the poll below or reply with a quick note—I read every response.

More next week.