Have you ever spent a quarter in the thick of your business? At the end, you finally pick your head up and ask yourself: Did we even move the needle in the right direction?

There’s usually a lot to unpack at this point, but two things worth highlighting:

I recently partnered with a business owner in this exact spot.

Successful business, outpacing the prior year, and yet the thread had been lost between the long-term vision and the work being executed in real-time.

Instead of immediately focusing on the next 90 days to course correct, we instead zoomed way out first.

We started with: What does this business look like 10 years from now?

So, instead of: What do I need to do next quarter?

We shifted to: What needs to be true in the next quarter to ensure the 10-year version of this business exists?

A quarterly plan is useless if there’s no connection to the broader long-term strategy.

Today, I’m breaking down how we walked this entire journey, from 2036 back to the next quarter in hopes it helps you the next time your team loses the plot.

If you’re familiar with EOS, this cadence is similar. What I’ll walk through is how using this structure actually played out with the business owner I mentioned above.

Before vision casting and then working our way back to the next 90 days, we first grounded ourselves in the present reality:

That framing helped us envision the future through a more informed lens. We focused on four layers, in the following order:

10 years - unconstrained, thinking big about “we made it” looks like, professionally and personally.

3 years - what needed to be in place structurally within this timeframe for the 10-year vision to manifest.

1 year - the concrete, focused goals over the next 12 months that move the needle meaningfully in the 3-year direction.

90 days - immediate execution and what needs to track for the 1-year plan to hit.

This way, at every move inward, we had our eye on the long-term North Star and aligned back to it at each layer.

We didn’t build a laundry list of tasks. We dug deep, got everything on the table and then I probed until we narrowed in on what really mattered. Less is more, and focus plus specificity wins in this type of exercise.

For example, you should have a single guiding statement for clarity on the 10-year vision. Three years out, you should know the 3-5 core things that need to be true and what your business will look like if it’s on track to achieving that vision. And so on.

This business owner has a plan and is bringing the team along the journey.

What do I suggest for you if you make it to this point?

Once you, and your core leadership team (if you’re at this stage), take the time away from the business to run through this, make sure the outputs are synthesized, documented and can be understood by all.

Then, it’s about communication and cascading messages. Think about how you’ll present the vision to the team. Discuss how the work you’re asking them to do in the nearer-term ladders up. The more they feel like part of the plan and can visualize their impact, the more buy-in you’ll see.

Reinforce an operating rhythm. Build the weekly, monthly, quarterly and annual rituals that enable monitoring, reporting, strategic discussions and changing course if needed.

None of this is particularly complicated. However, it takes discipline and building the right conditions for progress and accountability.

With this business owner, the outcomes were clarity and momentum. I checked in recently, and was pleased to hear at least one of the 90-day milestones had already been hit.

Let’s ask the question from the beginning again:

Did we even move the needle in the right direction?

If you do the work, you’ll have the answer way before the end of the next quarter.

Oply is a home management platform built to take the guesswork out of caring for your biggest asset. By combining smart tools with on-demand services, Oply makes it easier to track, maintain, and protect your home, all in one place.

Q: When did you know you were destined to build a business?
A: “I think I always had the entrepreneurial itch, but I knew I was destined to build a business when I watched my husband Gabe start, scale, and sell a home services business. I loved the challenges entrepreneurs face every day, the constant problem-solving, the ownership, the freedom to build something from nothing. Harvard Business School gave me the early-stage tools and frameworks to feel confident enough that I could actually do it myself, and we launched Oply out of Harvard's Innovation Lab. Looking back, the path makes sense. West Point taught me how to lead under pressure and trust my own judgment when the stakes were high. Flying Little Birds with the 160th SOAR taught me that the people who get things done are the ones willing to do the hard thing first and figure it out as they go. Gabe's operational background in home restoration gave us a real, lived understanding of where the home services industry was broken. And Harvard gave me the language, the network, and the playbook to translate all of that into a venture. By the time we launched out of the i-lab, building Oply did not feel like a leap. It felt like the natural next mission.“

Q: What’s the most unexpected thing (+/-) that’s happened along your entrepreneurial journey?
A: “The most unexpected thing has been the people who believed in us and what we were building. When you start a company, you brace yourself for a lot of doors closing. What I did not expect was which doors would open. We have Bill Ackman on our cap table, who is famously selective about where he puts his name and his capital. The Kraft Family, the owners of the New England Patriots, also believed in us early. These are not investors who write checks lightly, and having both on the same cap table still feels surreal some days. I have had the chance to pitch Kevin O'Leary, and Reese Witherspoon has personally mentored me through some of the most pivotal moments of building Oply.“

Q: When did you hit your first scaling challenge, and how did you overcome it?
A: “We are actually right in the middle of our first real scaling challenge. We spent the early days proving that homeowners genuinely want what we are building, and the organic traction we saw earlier this year told us the product was resonating. The challenge now is moving from organic momentum to a real growth engine, and doing it fast. A few things are converging at once. We just hired our first Lead of Consumer Growth to put fuel on the fire we already started, building out paid programs, lifecycle, attribution, and the full growth function from the ground up. At the same time, we are in late-stage conversations with a major warranty company where the incentives align almost perfectly with ours, which would unlock distribution in a way that is hard to replicate. And underneath all of it, we are getting the house in order operationally so we can move quickly heading into our Series A. The way we are overcoming it is the way we have overcome everything so far: hire people who are better than us in their lane, make sharp decisions with the information we have, and stay close to the customer so we never lose the thread of why we exist. The next chapter is about scaling without losing the soul of what made the early product work, and that is the challenge I am most excited to take on.“

Q: If you were starting all over, what’s one piece of advice you would give yourself?
A: “If I were starting all over, I would tell myself a few things. First, be bold. Get rid of the impostor syndrome early because it will cost you more time and more opportunities than any actual mistake ever will. Trust your judgment. Your gut is usually right, and the moments I have second-guessed mine are almost always the moments I wish I had moved faster. Second, do not get seduced by shiny resumes. The pedigree on paper rarely correlates with the grit you actually need in a startup. The best people I have hired are the ones who run toward hard problems, not the ones with the most impressive logos behind them. And finally, hire slow, fire fast. Every founder hears this and almost no one actually does it. The cost of holding on to the wrong person is always higher than the discomfort of making the change. Protect the team you are building, because in the early days, the team is the company.“

Q: Do you have one ask or offer you would like to share with the Empower community?
A: “Yes, and it is a simple one. Use the app. Download Oply from any app store, try it out, and put it through its paces. If you love it, leave us a 5 star review in the app store because it genuinely helps us with reach. Share it with your neighbors, your family, the friend who is always texting you about a leaky faucet or a contractor they cannot get to call them back. Most importantly, tell me what you think. I want the good feedback and the bad feedback, especially the bad. Every honest piece of input makes the product sharper and gets us closer to the home management experience homeowners actually deserve.”

Q: A fun one, what’s your all-time favorite restaurant and where is it located?
A: “My all-time favorite restaurant is my dad's kitchen. He is a phenomenal cook, and he and my mom make such a great team in the kitchen. Every Sunday, the whole family in Nashville gets together at their house for dinner, including my daughter, their first granddaughter, and the meals are always more thoughtful and better prepared than anything you would find at a restaurant. His killer filet mignon with lobster mac and cheese is genuinely to die for.“

As Lindsey said, download the Oply app and check it out for yourself!