Too much information, too many choices, not enough time... that is where good intentions go to die and where real planning begins.
It was the summer of 2014, and everything in life was changing at once. My wife and I had just sold our first condo in River North after spending six months hunting for the right place to start a family in a market with very little inventory. We finally landed on a vintage condo on Lake Shore Drive in Lakeview, inside a 1927 building with a storied history, tucked beside a beautiful synagogue and looking out over Lake Michigan. The unit was a three bedroom, three bath home - about 700 square feet larger than anything else we could find - and roughly $250,000 less than comparable places. The catch: it needed a lot of work.
We bought it at an estate sale. The prior owner had lived there for 55 years, and we would be only the third family to call it home. At closing, we met her daughter and listened to stories of her childhood in the unit. The finishes were a mix of timeless craftsmanship - handmade wood arches, a fullsize dining room with an artdeco chandelier - and a very retro but not in a good way 1980s kitchen. The attraction was simple: this was a blank canvas, a chance to make the space our own before our first child arrived that October.
It became obvious almost immediately there was no way we could manage the renovation on our own. The project was too complex, with too many moving parts, too many decisions, and not enough time in our already full lives. So we did something no one in our family or friend group had done before: we hired a designer, Alison Besikof, along with a general contractor she recommended and a few trusted specialists tailored to the job. The plan was to remodel the kitchen, two bathrooms, and more, without losing our minds or our budget in the process.
One of the first stops with Alison was a tile showroom. If you have never walked into a tile store with a remodel on the line and a baby on the way, picture this: thousands of options stacked to the ceiling. Different colors. Different textures. Different sizes. Natural stone and manmade materials. Subway tile, hex tile, patterns you never knew existed. Everything was technically available to us, but nothing was obviously right for us.
Alison greeted us calmly and said, “Take your time. Walk around.” We had already sent her dozens of photos from Pinterest and Instagram, hoping our “research” would make us prepared. We were not. Within minutes it hit me: I had no process for thinking about what I was seeing.
Every question mattered. None of the answers were obvious. And there was no chance to learn it all from scratch while still being present for work, family, and a baby on the way. Any lingering doubt about the value of hiring Alison evaporated right there between the sample boards.
Left to our own devices, we were headed down one of two paths: either spend far too many nights and weekends obsessing over tile we were not qualified to evaluate, or make rushed, random choices we would later regret and pay to fix. Neither path made sense. Alison, on the other hand, already knew how the pieces fit together. She knew which materials would age well, which combinations worked, how the total cost stacked across the entire project, and where it was worth splurging or saving.
After about 30 minutes, she brought us three tile options she had preselected in the style we had in mind. She explained where each would go, how they worked together, and the pros and cons of each choice. The tile looked incredible, and we most likely would never have found it on our own - in some cases because there were eight nearly identical versions, and she knew which specific one belonged in our home. We did not just hire a designer; we bought back our time, our sanity, and a much higher probability of a good outcome. Throughout the remodel, Alison kept turning overwhelming questions into just a few clear choices, moving us from 3,000 options down to 3.
Every one of these is a “tile.” Each website, podcast, TikTok, or blog adds ten more sample boards to your cart of options to evaluate. And just like that tile store, the real problem is not a lack of options.
Human brains are built to keep us alive in the wild, not to optimize complex financial systems over the next 12 months to 12 years. Faced with too many choices and not enough time, even high income, highly intelligent people tend to default to one of three moves:
That tile store embodied all three tendencies. So does the modern financial internet for most firsttime wealthy professionals.
In that showroom, more information would not have helped. Reading every label, comparing every spec sheet, binging remodel videos - it all would have increased the illusion of control without meaningfully improving the final result. What helped was our guide.
In the tile store, the cost of Alison’s fee was tiny compared with the cost of bad decisions, wasted weekends, and living every day in a home that never quite felt right. In your financial life, the same equation applies—only with more zeros, more years, and far more at stake than the tiles beneath your feet.