Prepping Your Books for Tax Season is one of those topics that can make even the most organized, creative business owner want to close their laptop and pretend it’s not January.

So before we dive in, I want to say this gently: if you’re coming out of the holidays feeling behind, overstimulated, or like you need to “get your life together” overnight, you’re not alone. The first part of the year has this weird energy where everyone suddenly wants you to be refreshed, productive, and financially responsible… immediately.

But if tax season already feels heavy, you don’t need more pressure. You need a plan that feels calm, doable, and supportive.

That’s exactly why I recorded this episode and why I’m turning it into a long-form blog post. Because Prepping Your Books for Tax Season isn’t just a “numbers” task. It’s a clarity task. It’s a nervous system task. And honestly, it’s a confidence task, too.

I brought on my bookkeeper (and friend), Hailey Fernelius of Hailey Ann Co, because she’s one of the only people I know who can talk about QuickBooks and money mindset in the same breath and make it feel… grounding. She’s a former wedding planner, a numbers girl at heart, and now she also offers somatic money coaching, which is such a missing piece in the creative industry.

If you’ve ever felt like you’re doing everything “right” in your business, but you still don’t feel safe with money, you’re going to feel very seen in this conversation.

🎧 Listen to this episode on Spotify or Apple Podcasts or play it directly here.

Why Prepping Your Books for Tax Season matters more than you think

Let’s start here: most wedding and event pros don’t avoid bookkeeping because they’re lazy.

They avoid it because:

• It feels confusing
• It feels emotionally loaded
• It brings up fear (even when the numbers are fine)
• They’re scared of doing something wrong
• They’re worried they’ll discover a “problem” they can’t fix

And that’s what Hailey and I kept coming back to: you can’t build an elevated brand, make confident business decisions, or market sustainably if you’re disconnected from your numbers.

Because your numbers are not just your taxes. They’re also:

• your pricing strategy
• your profitability
• your capacity
• your hiring decisions
• your marketing budget
• your ability to grow without burning out

So yes, this is a tax-season conversation. But it’s also a business longevity conversation.

And if you’re someone who wants a more elevated brand, more consistent bookings, and more peace in your business, this matters.

Meet Hailey Ann Co: bookkeeping, but make it supportive

Hailey’s story is one I love because it’s so honest. She started in the wedding industry as a planner and realized pretty quickly what was and wasn’t her zone of genius. She loved the operational backend. Money management. Systems. Organization.

And she built Hailey Ann Co because she saw a gap: so many wedding pros are wildly talented at their craft, but they’re doing tasks that drain them and take way longer than they should.

Bookkeeping is one of those tasks.

As Hailey said in the episode, it’s not the kind of thing you can do with a TV show playing in the background. It requires full focus. And if it’s not your wheelhouse, it’s miserable.

But she loves it. And that matters. Because the best person to handle your finances is someone who genuinely enjoys the work and knows how to communicate it in a way that doesn’t make you feel stupid.

What I also love is that Hailey isn’t just a bookkeeper. She’s one of the only people I know who bridges the gap between:

• the logic of money (QuickBooks, reports, deductions, categories)
• and the emotional reality of money (fear, scarcity, avoidance, nervous system responses)

Because the truth is: most of us aren’t struggling with numbers alone. We’re struggling with what numbers represent.

The problem with “just manifest it” money advice

This came up in our conversation and I’m so glad it did.

There’s a lot of money mindset content online that sounds like:

• “Just raise your prices”
• “Charge your worth”
• “Act as if”
• “Repeat these affirmations and you’ll hit six figures”

And listen, I’m not anti-mindset work. I’ve done a ton of it myself.

But here’s the gap that Hailey named so clearly:

Some money coaches don’t actually know the numbers.

And some bookkeepers know the numbers, but don’t understand the emotional side of money at all.

So creatives are often stuck choosing between:

• logic without compassion
• or inspiration without strategy

And neither one actually serves you long-term.

Hailey’s approach is different because she’s not trying to hand you a “magic answer.” She said something I wish more educators would say:

“You don’t need me. I’m here if you want me. I’ll teach you. I want you to be able to do it yourself.”

That alone is a green flag, especially in an industry where so many people market themselves as the only solution.

Money stories: why two people can have the same numbers and feel totally different

One of my favorite parts of this episode is the conversation about money stories.

Because money is one of the most emotional things we deal with, and it’s rarely talked about honestly. You can have two people with the same:

• income
• debt
• savings
• revenue

…and one person feels calm while the other feels panicked.

That’s why I always say: you can’t assume someone’s financial reality based on numbers alone.

Hailey explained that these stories often start early, based on what you heard or witnessed growing up:

• “We can’t afford that.”
• “Money doesn’t grow on trees.”
• “We don’t have enough.”
• or the opposite: money was always available, spending was normalized, debt wasn’t scary

But what really matters is how your nervous system learned to respond. Because those stories don’t stay in your head. They show up in your behavior.

How money stories show up in your business decisions

Hailey shared a few ways this can look in real life, and I want you to reflect honestly here. No judgment.

You might be money-triggered if you:

• hold your breath when you hit “submit” on a purchase
• avoid looking at your bank account altogether
• over-research every investment to the point that you never decide
• delay booking support even when you know you need it
• feel guilty spending money on your business
• feel guilty charging what you need to be profitable
• swing between overspending and total restriction

None of this means you’re bad with money. It means your body is trying to keep you safe.

The nervous system archetypes: fight, flight, fawn, freeze

Hailey ties a lot of her work into nervous system responses, and she shared a framework that makes so much sense.

When it comes to money and business decisions, you might default to:

• Fight: spend quickly, move fast, invest impulsively, trust you’ll “figure it out”
• Freeze: research endlessly, wait until you’re “ready,” struggle to take action
• Flight: get close to action, then back out, avoid follow-through
• Fawn: ask for advice, buy the program, get the support… then don’t implement because you don’t want to be seen taking action

What I love about this is that it removes shame.

Instead of thinking “I’m just bad at money,” you can start thinking:
“What response is my nervous system in right now, and what would help me feel safer?”

Because that’s the real work.

And it’s also why cookie-cutter affirmations don’t always help. If your body doesn’t believe the story you’re repeating, your nervous system won’t integrate it.

What abundance actually means (and what it doesn’t)

I love the word abundance, but Hailey said something that I want to underline:

You can’t outsource your power.

If your relationship with abundance looks like:

• “This podcast will fix my life”
• “These affirmations have to work or I’m doomed”
• “If I don’t do this perfectly, I won’t be successful”

That’s not abundance. That’s pressure dressed up as self-help. Abundance is when you feel grounded enough to believe:

• you can handle money
• you can make decisions
• you can recover if something doesn’t work
• you can create safety and growth over time

And that takes both mindset and strategy, which brings us back to the practical side of this episode.

Prepping Your Books for Tax Season: what to do right now

If you’re reading this and thinking, “Okay, I get it. But what do I actually need to do?”

Here’s your starting point.

1. Look at your Profit & Loss report (P&L)

Your P&L tells you:

• what you earned
• what you spent
• what your profit actually was

This is the report most business owners avoid because it feels like a wall of numbers. But avoiding it doesn’t protect you, it just delays your clarity.

If you have a bookkeeper, ask them to send you a simplified summary (Hailey calls it the “Cliff Notes” version). If you don’t have a bookkeeper, set aside 30 minutes to pull it up and simply observe.

No spiraling. Just data.

2. Categorize your transactions

Hailey said this clearly: if your expenses are not categorized, you’re leaving money on the table.

Different expenses have different deduction rules. A meal is not the same as a laptop. Software is not the same as travel. Supplies are not the same as equipment.

If you’re not tracking properly, you may be:

• missing deductions
• overpaying taxes
• scrambling at the last minute
• or mixing personal + business in a way that creates confusion

3. Stop mixing personal and business spending

If you have business expenses coming out of personal accounts, it doesn’t mean you’re doomed. But it does mean tax prep gets messier.

If you’re early in business, this is a powerful “clean up” goal for this season:

• separate accounts
• separate cards
• clear labels
• consistent systems

The goal is to make your business feel like a business.

4. Don’t rely on “it’s a write-off” energy

This part made me laugh because it’s such a stereotype.

Not everything you buy is deductible just because you work near it.

No, your daily coffee shop latte isn’t a business expense just because you brought your laptop. DoorDash to your house isn’t a “business lunch” unless it’s truly business-related in a legitimate way. Dinner with your spouse every night is not a write-off because you talked about work.

Write-offs are real, but they are not a free-for-all.

The point is to track what’s legitimate, maximize what’s allowed, and stay clean.

5. Save on taxes by paying the right people, not overpaying the government

This was one of Hailey’s strongest points and I agree with it: don’t overpay taxes just because you didn’t track your expenses.

If you’re going to spend money anyway, I would rather you spend it on:

• a bookkeeper
• an accountant
• a financial pro who understands your industry

…than throwing extra money away because you didn’t want to deal with your books.

Not because taxes are bad, but because you get to choose where your dollars go when you run a business. And yes: always pay your taxes legally. Do not play games with that.

Common misconceptions wedding and event pros have about taxes

A few clarifying points that came up in the episode that I think are worth repeating:

Travel can be deductible if it’s truly business-related
If at least 50% of your trip is business-focused (conference, meetings, content creation, business activities), travel can be a legitimate business expense.

This is one of those areas where I strongly recommend talking to a pro, because the details matter.

Buying a car at the end of the year “for the write-off” is not always smart
This is such a common move, and Hailey said it plainly: if your business can’t comfortably handle the ongoing payments, you’re not saving money—you’re creating stress for future you.

Also, if you sell too quickly, you can create another tax issue. Again: strategy, not impulse.

Revenue is not profit
Please tattoo this on your brain.

If someone says they had a $500k year, you still don’t know:

• how much they spent
• what their take-home was
• whether they were profitable
• whether they were in debt
• whether that growth was sustainable

This is why comparing yourself to revenue numbers online is such a trap.

If you feel overwhelmed by your numbers, start here

This is the part I want to end with, because I know someone reading this is in the “avoidance spiral” and you’re hoping this blog will magically fix it.

If your books feel overwhelming:

• slow down
• notice what you feel in your body
• name what the fear is
• get support before it becomes an emergency

Because you’re not broken. You’re human. And if no one ever modeled business finances for you growing up, it makes sense that you feel unsure now.

A lot of creatives were not raised by women who were entrepreneurs. A lot of us don’t have examples in our immediate circle. That doesn’t mean you can’t do this. It just means you need systems and support that meet you where you are.

How to work with Hailey Ann Co

If you need help Prepping Your Books for Tax Season, Hailey can support you in a few different ways:

• book cleanup (getting your books current and categorized)
• ongoing bookkeeping
• teaching you how to manage your own books
• somatic money coaching (one session or multi-month support)
• combined packages (numbers + nervous system)

She also offers The Overflow Room, an online library of somatic routines and targeted exercises, plus guest expert sessions that help you learn while you move your body.

Prepping Your Books for Tax Season is not just a compliance task.

It’s a business maturity moment, it’s choosing to stop guessing, it’s choosing to stop paying and praying,
it’s choosing to build a business that feels stable, sustainable, and supportive of the life you want.

Because the truth is: you can’t build a brand you feel proud of if the money side of your business feels chaotic.

And you don’t have to do this alone.

Listen to the episode

You can listen to “Prepping Your Books for Tax Season with Hailey Ann” on Spotify or Apple Podcasts, or by pressing play here on the blog.