How Founders Can Build a 2026 Schedule That Actually Works

Inside Startup Boston & City of Boston’s year-end planning panel

With just weeks left before the calendar turns over, Startup Boston and the City of Boston brought together three seasoned founders - each with wildly different entrepreneurial journeys - to tackle a deceptively simple question: How should founders actually plan their 2026 schedule?

Moderated by Startup Boston founder Stephanie Roulic, the conversation quickly moved beyond calendars and time-blocking. What unfolded was something closer to a founder survival guide—equal parts strategy, mindset, and honesty.

This year’s panel brought together three leaders whose experiences span hardware, deep tech, e-commerce, academia and advisory work:

Michelle Chao — Deep Tech Operator & Former Phoenix Tailings COO

Started in R&D at Markforged before helping scale the company from 70 to 400 employees. Later co-founded Phoenix Tailings, raising $70M+ and growing the team from four people to 40. Now advises early-stage founders.

Rabeeh Majidi — Engineer, Educator & Wearable Health Tech Founder

A PhD in electrical and computer engineering, Rabeeh has worked across academia, corporate innovation and startups. As CEO of OrthoKinetic Track, she’s building sensor-embedded garments that monitor joint injuries. She’s also a longtime Startup Boston volunteer with firsthand experience navigating accelerators, grants, and early-stage chaos.

Rebecca Moore — Early Dot-Com Founder, Advisor & Angel Investor

Launched MuseumShop.com during the dot-com boom, raising $10M and partnering with 70 museums. Today, she coaches women founders, helps startups become capital-ready, and has invested in 15+ companies.

Together, they delivered a candid, 360° look at what it really takes to build a sustainable founder schedule - and the missteps, burnout cycles and lessons learned along the way.

Before diving into the insights below, you can watch the full panel recording on YouTube, embedded right below:

Here’s what today’s founders are walking into 2026 with - and the systems that can keep them from burning out before Q2.

Start With the Big Vision—Then Be Brutally Realistic

Founders love big goals. But as Phoenix Tailings co-founder and former COO Michelle Chao reminded the audience, the first step isn’t deciding what you want to do, it’s deciding what actually matters.

At the end of each year, Chao boards a plane with no Wi-Fi and sits down with three lists: personal goals, professional goals, and business goals.  “I brain dump everything,” she said. “Then I look for the overarching theme: What’s the one thing I’ll be proud to have accomplished by the end of the year?”

For her, that high-level clarity becomes the anchor for everything else, down to the weekly OKRs her team set throughout their Techstars days.

For Rabeeh Majidi, founder and CEO of Ortho Kinetic Track, realism starts with the pitch deck. “You all have your milestones,” she said. “But I’d ask myself: Do I actually have the funding, the people, and the capacity to achieve the things I’m telling investors I’ll achieve this year?”

The answer, she admitted, changed almost quarterly.

The Power of Weekly Intentions (and Why Three Is the Magic Number)

If the panel agreed on anything, it was this: founders should stop worshipping the annual plan.

High-level plans matter, but according to Rebecca Moore, startup advisor, early internet entrepreneur and angel investor, real progress comes from the short cycle.  “You need your one-year horizon,” she said, “but you should be spending most of your time planning for the next 12 weeks. Every week is a month in startup time.”

Moore recommends choosing three weekly priorities. Not seven. Not twelve. “If you get those three done, you are moving the needle,” she said, likening the discipline to physical therapy: possible alone, but infinitely more effective with accountability.

And accountability, the group emphasized, is non-negotiable - especially for solo founders. “You need someone else to say your goals out loud to,” Chao added. “Even if it’s just emailing an advisor. It changes how you show up.”

Handling the Unexpected: Firefighting Without Losing Focus

Startups change fast, and the unexpected is unavoidable. The real question: How do you know when a surprise deserves your attention?

Chao offered the most tactical framework: urgency vs. importance. “There are things that are urgent but not important,” she said. “And things that are important but not urgent. You need to know the difference, fast.”

Moore distilled it further: “If it hits the bottom line, deal with it immediately.”

Majidi emphasized the role of mentorship - specifically the right mentors. “There are some mentors who always say, ‘You’re great, just keep going,’” she said. “And others who say, ‘I told you this would happen.’ You need someone who gives you grounded, balanced feedback.”

But ultimately?  “As CEO, you own the decision,” Moore said. “You need to develop your inner validation muscle.”

The Daily Grind: How Founders Actually Get Work Done

The audience lit up around the question every founder wrestles with: How am I supposed to get anything done between emails, pitches, meetings, emergencies, and life?

Moore again pointed to the top-three rule: return to your weekly intentions, every time you feel lost. “Your inbox will survive until after you finish the important things,” she said.

Chao takes a ruthless approach to context-switching: “If I’m interviewing, I block a full afternoon. If I’m doing investor updates, that’s all I’m doing. Don’t compromise once you’ve blocked the time.”

Majidi conducts her CEO planning on Sunday nights: “I look at my week and ask: Do I really need this meeting? Can I move it? Can I cancel it?” she said. “Then I rebuild the week based on what truly matters.”

The Topic Founders Hate Talking About: Time Off

Every founder knows they need rest. None want to take it.

Chao admitted she made it through an entire fundraising cycle without a single break. “I was running at maybe 40% efficiency,” she said. “When I finally took a real vacation - no phone, no investors - I had more clarity in eight hours than I had in months.”

Moore shared an even more stark story: During her first startup, she gave birth to her first child with her team working in the finished basement of her home. “I’d run upstairs, nurse, run downstairs,” she said. “Seven years of adrenaline. I do not recommend it.”

Majidi, too, worked through extreme personal moments, including submitting an SBIR grant with a five-day-old newborn at home. “Looking back, I ask myself: Why did I do this?” she said. “Nothing is more important than your health. You are the asset.”

Their message to founders was unanimous: If you burn out, your company burns with you. Build in rest intentionally - or pay for it later.

Tools That Actually Work

Despite the rise of founder-productivity apps, the panel stayed refreshingly grounded.

Chao: “Spreadsheets. Everyone knows how to open one. Everyone can update one. At the end of the day, it just works.”

Majidi uses a more experimental AI-driven incubator platform that scores startups and tracks risk over time—helpful, she said, but not necessary.

Roulic offered her own founder trick: turn your Google Calendar into a live to-do list.

Meanwhile, Moore tried nearly every tool on the market before reverting to the basics: “I found I was spending more time updating the tool than doing the work,” she said.

The One Piece of Advice They Want Founders to Carry Into 2026

As the conversation wrapped, each founder offered a “hot tip” for the year ahead:

Michelle Chao: “Focus. Pick your top three. And actually do them.”

Rabeeh Majidi:  “Don’t rush into building a business you’re not ready for. And don’t sacrifice your family - they matter as much as your company.”

Rebecca Moore:  “Build your kitchen-table crew - the people who will hold you accountable. And if something doesn’t get done, don’t beat yourself up. Revisit, reset, move forward.”

A 2026 Approach Rooted in Discipline, Boundaries, and Human Needs

If there was one thread running through the entire session, it was this: Founders don’t need a more complicated system. They need a more compassionate one.

One built on clarity of purpose. One that leaves room for course-correction. One that acknowledges founders as humans with bodies, families, limits and needs. And one where you don’t need to conquer the whole year at once - just the next three priorities.

Want to hear all the nuance, stories, and unscripted moments? Watch the full panel recording on YouTube, embedded at the top of this article.