What if the reason your business feels stressful isn’t more work, it’s how you’re handling your money?

In this episode, Megan Schwan pulls back the curtain on the financial mistakes almost every solopreneur makes (especially early on) and how to fix them without becoming a numbers nerd.

We’re talking pricing mistakes, scope creep, avoiding your books, fearing taxes, and why most solopreneurs are unknowingly treating themselves like underpaid employees. Megan breaks down bookkeeping systems, tax strategies, and the Profit First method in a way that actually makes sense, and helps you step fully into the CEO role.

If you’ve ever said, “I’ll look at my numbers next month,” this episode is for you.

Episode FAQs

What bookkeeping systems do solopreneurs really need to stay organized?

You don’t need complicated spreadsheets or expensive tools, but you do need structure. Megan recommends:

• A real accounting software (like Wave, QuickBooks Online, Zoho Books, or Xero)
• A mileage and receipt tracking system to capture deductions
• A cash flow management system like Profit First to prioritize paying yourself, saving for taxes, and stabilizing cash flow

These systems help you treat your business like a business, not a side project.

What’s the first step if finances feel overwhelming or intimidating?

Start doing your bookkeeping consistently. Megan emphasizes scheduling regular time to work on your business, not just in it. Reviewing your reports and understanding where your money is going builds confidence, clarity, and better decision-making. Avoiding the numbers only makes problems bigger later.

How can solopreneurs become more recession-proof?

Two big moves:

• Create a budget so you have a plan for your money and can ask smarter questions when numbers don’t match expectations.
• Save for taxes proactively (about 8–15% of sales) so tax bills don’t derail your cash flow or peace of mind.

Megan also explains how Profit First helps solopreneurs build “real profit” and spot issues before they become emergencies.

🌟 Featured Resource: LifeStarr Intro for Solopreneurs

Are you building a business on your own and feeling like you’re going it alone? That stops today. LifeStarr Intro is a free, forever membership built especially for solopreneurs who want real support, real resources, and real community.

When you join LifeStarr Intro, you unlock:

• A vibrant community of like-minded solopreneurs for feedback, encouragement, and connection
• The LifeStarr productivity app (coming soon), built to support your workflow using GTD principles (that’s Tasks, Projects, Inbox that works)
• Live problem-solving meetups, expert sessions and strategies...and you don’t pay a thing

Total value: $65/month. Your cost? Zero.

👉 Ready to stop struggling solo and build a business that works for you?

Join LifeStarr Intro for Free

If the holidays feel like a chaotic mash-up of family gatherings, last-minute tasks, and pressure to magically “figure out next year,” this episode is your breath of fresh air.

Carly and Joe break down why December is actually the perfect time to prep your business, without overhauling your life, and how reconnecting with your why can completely change the way you enter 2026. They’ll walk you through mini-detox habits that clear mental clutter, lifestyle-first planning that puts joy back on the calendar, and small routines you can start now to build real momentum before January even arrives.

FAQs From The Episode

How early should I start planning for the new year?

Earlier than you think, but not in an overwhelming way. December is a great month to ease into planning by reconnecting with your personal and professional “why,” cleaning up digital clutter, and building tiny habits you want to bring into 2026. You don’t need a full-year plan, focus on your first 90 days, because it’s specific enough to take action but flexible enough to pivot as things change.

What should I prioritize during a December “business detox”?

Stick to high-impact clean-ups that reduce mental load: unsubscribe from emails you never read, unfollow accounts that drain your energy, organize your workspace, clear your desktop, and gather scattered to-dos into one place. These small resets set the stage for clearer thinking and a calmer January, without requiring hours of work.

How do I build new habits for 2026 without burning out before the year even starts?

Start practicing them now in micro-form. If you want to wake up earlier, try doing it one or two days a week in December. If you want to spend 10 minutes engaging on LinkedIn every morning, start this week. If you want to guard your deep-work hours, experiment with checking email later in the day. You’re not aiming for perfection, just building familiarity so January doesn’t feel like a hard reset.

🌟 Featured Resource: LifeStarr Intro for Solopreneurs

Are you building a business on your own and feeling like you’re going it alone? That stops today. LifeStarr Intro is a free, forever membership built especially for solopreneurs who want real support, real resources, and real community.

When you join LifeStarr Intro, you unlock:

• A vibrant community of like-minded solopreneurs for feedback, encouragement, and connection
• The LifeStarr productivity app (coming soon), built to support your workflow using GTD principles (that’s Tasks, Projects, Inbox that works)
• Live problem-solving meetups, expert sessions and strategies...and you don’t pay a thing

Total value: $65/month. Your cost? Zero.

👉 Ready to stop struggling solo and build a business that works for you?

Join LifeStarr Intro for Free

In this episode, Will Simpson gets honest about the moment he realized he didn’t want a boss. He breaks down the identity crisis that hit after leaving decades of COO/CTO life, the surprising advantage founders over 40 actually have, why solopreneurs must unlearn corporate thinking, and how embracing “good enough” is the key to launching anything.

If you’ve ever wondered whether you’re too late, too structured, too corporate, or too unsure to build something of your own…this conversation is the permission slip you’ve been waiting for.

FAQs From The Episode

What makes this episode valuable for solopreneurs who come from the corporate world?

Will explains exactly why corporate experience does translate, just not in the ways you think. He talks through the mindset traps, the “ambient stress” you leave behind, and how to rewire yourself for small-ball thinking, fast execution, and building something that actually energizes you.

Does Will think it’s harder to become a founder after 40?

Not at all, he argues the opposite. According to Will, founders over 40 bring unmatched domain expertise, resilience, and clarity. The data supports it, and he shares why experience gives mid-career professionals an overlooked edge that younger founders simply can’t replicate.

What’s Will’s top advice for solopreneurs who want to use AI or no-code tools?

He stresses that AI can help you build prototypes fast, but not without structure, constraints, and actual expertise guiding it. He breaks down why you can’t “speak” a fully functional app into existence, how to think like a builder instead of a coder, and why you should ship an MVP that’s slightly embarrassing.

🌟 Featured Resource: LifeStarr Intro for Solopreneurs

Are you building a business on your own and feeling like you’re going it alone? That stops today. LifeStarr Intro is a free, forever membership built especially for solopreneurs who want real support, real resources, and real community.

When you join LifeStarr Intro, you unlock:

• A vibrant community of like-minded solopreneurs for feedback, encouragement, and connection
• The LifeStarr productivity app (coming soon), built to support your workflow using GTD principles (that’s Tasks, Projects, Inbox that works)
• Live problem-solving meetups, expert sessions and strategies...and you don’t pay a thing

Total value: $65/month. Your cost? Zero.

👉 Ready to stop struggling solo and build a business that works for you?

Join LifeStarr Intro for Free