Kindled Planning

06/23/2026

Big shoutout to the North Central Massachusetts Chamber of Commerce! They do an amazing job creating meaningful networking opportunities for local businesses. Kindled Planning is proud to support the North Central Golf Tour as a Hole Sponsor and invest in our local community!

06/22/2026

The summer solstice just passed, the longest day of the year.

More daylight is great. A surprise tax bill in April? Not so much.

The solstice is actually a perfect reminder that you're halfway through the tax year. Here's what to check right now:

✅ Are you withholding enough?
✅ Have you made your Q2 estimated payment?
✅ Did anything change this year, new job, equity vest, side income?

A 30-minute mid-year check today can save you thousands come April. The sun isn't slowing down, your tax planning shouldn't either.

05/31/2026

Excited to share something I have been working on, The Kindled Brief, a monthly newsletter from Kindled Planning focused on equity compensation and tax complexity. Whether you have RSUs, stock options, or a pending liquidity event, or you run a business and want to stay ahead of your tax situation year round, this was built for you. Think of it as an extension of what we do at Kindled Planning, practical planning insights to keep you informed all year, not just at tax time. Current clients are already subscribed and Issue 001 goes out tomorrow. If you want on the list visit

One email a month to help you keep more of what you earn.

05/27/2026

Kindled Planning is excited to be a sponsor of the 8th Annual Unified 5k, an inclusive road race and adaptive sports expo in Lancaster, MA this Saturday, May 30th. Participants can walk, run, or roll the 1 mile or 5k distance or join us for a kids fun run with the Railers and Woo Sox mascots. The event raises money for the AdaptX grant program that provides adaptive athletes with running prosthetics, sports wheelchairs, and the equipment that they need to accomplish their goals. We invite you to join us on Saturday at RFK Community Alliance in Lancaster for this impactful event.

04/24/2026

The most expensive phrase in the tax industry is "I wish I knew that sooner".

Ask any tax professional what they hear most often during the April filing deadline, and they’ll tell you it’s a version of that same sentiment. High-performing professionals and business owners often realize they left money on the table simply because they only looked at their taxes once a year.

The truth is, there is a fundamental difference between a Tax Preparer and a Tax Advisor:

📜 The Tax Preparer is the Historian. Their role is vital for compliance, they look in the rearview mirror to ensure your financial history is recorded accurately for the IRS. They are experts at documenting where you’ve already been.

👨‍✈️ The Tax Advisor is the Co-Pilot. We look through the windshield. Our job is to sit beside you during the calendar year, helping you "steer" toward savings opportunities and avoid tax turbulence before the window closes on December 31st.

Why having a Co-Pilot matters for your 2026 flight path:

🚀 For Business Owners: It’s the difference between losing money as a Sole Prop versus optimizing an S-Corp, or ensuring equipment purchases take advantage of 100% bonus depreciation rules.

📈 For Equity Holders: It’s about identifying "withholding gaps" on RSUs or AMT traps on ISOs before they turn into a massive April bill.

🏠 For Growing Families: Even if your situation feels standard, a co-pilot helps you maximize HSAs, time investments, and execute strategic charitable giving.

At Kindled Planning, we believe taxes are a year-round journey. Serving clients digitally across New England, we act as the co-pilot for the consistent check-ins that make a real impact. It’s not uncommon for these proactive strategies to save our clients tens of thousands of dollars over the long haul.

You don't need a "hack" in April; you need a Co-Pilot year-round.

04/23/2026

Sterling roots. Lancaster anchor. New England reach. 📍💻

If you recognize the name Nashoba, you know exactly where my heart is. I grew up in Sterling, went to middle school here in Lancaster, and spent my high school years just down the road in Bolton.

Opening an office in the heart of Central MA wasn't just a business move, it was a homecoming.

But I want to be clear about how we work: Kindled Planning is, and always will be, a digital-first practice. Our secure, paperless operations allow us to serve tech pros in Boston, founders across Massachusetts, and equity holders across all of New England with total efficiency.

So, why the office? Because some decisions are too big for a quick Zoom. I’ve reserved this space, The Strategy Hub, specifically for high-stakes, in-person deep dives:

🏢 Entrepreneurs: Mapping out a multi-year exit or S-Corp transition to save thousands in self-employment taxes.

📈 Equity Holders: Navigating the "Tax Traps" of a major RSU or ISO vest to avoid a massive April surprise.

We aren't a traditional "walk-in" tax shop. We fulfill your practice needs digitally by default, but we’re here in person when the strategy gets deep.

Virtual speed. Local roots.

04/22/2026

Emerging from the "Tax Fog" with a new perspective. 🌫️➡️☀️

It’s been a week since the filing deadline, and at Kindled Planning, we’ve finally caught our breath. Serving so many families and founders in our first full year was a marathon, and the feedback we’ve received has been incredible. Thank you to everyone who trusted us!

But as the dust settles, I want to share how we are evolving.
Most people see a tax pro as a historian, someone you hire once a year to report the past. That is a tax preparer. At Kindled Planning, we are Tax Advisors.

Why does this matter for you?
🚀 For Entrepreneurs: We focus on entity optimization and CFO-level strategy so you aren't losing money through inefficient structures.

📈 For Equity Comp Holders (RSUs/ISOs): We specialize in closing the withholding gap and managing the AMT traps that turn your hard-earned stock into a surprise bill.

💻 Digital-First | Locally Rooted: While we serve clients virtually from Connecticut to Maine, we’ve officially opened our office in Lancaster, MA for deep-dive strategy sessions.

The biggest savings don’t happen in April; they happen now, while we can still steer the ship.

Expect to hear from us daily this week as we share lessons learned from this past season to keep more money in your pocket.