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Why Your Business Feels Heavier Than Your 9-5 (And the 3 Questions That Will Fix It) – The Fail To Win Podcast Episode 327
Home » Blog » Why Your Business Feels Heavier Than Your 9-5 (And the 3 Questions That Will Fix It) – The Fail To Win Podcast Episode 327

Why Your Business Feels Heavier Than Your 9-5 (And the 3 Questions That Will Fix It) – The Fail To Win Podcast Episode 327

February 17, 2026 By fastforwardamy Leave a Comment

You didn't start your business to feel trapped.

You started it for freedom. Flexibility. The ability to design your days around what matters to you. But if you're honest, you might have less freedom now than you did in your 9-5. Your calendar is full. Your to-do list never ends. And somewhere along the way, you stopped enjoying the business you built.

This is what I call the freedom drift. It's not your fault, and you didn't consciously choose it. But it happened by default. You said yes to clients because you wanted to help people. You added team members because you needed support. You filled your calendar because things needed to get done.

And now you wake up dreading your day because it's full of things you never wanted to do in the first place.

Listen to the full episode for the complete story.

The Freedom Drift: When Success Starts to Feel Like a Trap

More than 50% of businesses close in the first 5 years due to cashflow problems. But I haven't seen much research on how many people close their businesses because it doesn't feel aligned anymore.

I've been in business for 10 years, and I've watched this pattern play out over and over. Entrepreneurs build impressive businesses that look great on paper. The revenue is there. The clients are there. But the person running it is exhausted, overwhelmed, and wondering if they should just go back to working for someone else.

The truth is, your business doesn't magically evolve with you. As you grow and change, your business stays the same unless you intentionally redesign it. Maybe you became a mother. Maybe you discovered you're more introverted than you thought. Maybe the pace you were willing to maintain 3 years ago is destroying your health now.

Your business needs to know who you are today, not who you were when you started.

The 3 Questions That Reveal Where You've Drifted

Every quarter, I do a freedom audit. It takes 15 minutes, and it's the reason I can record this podcast while looking at palm trees and spend an hour on the beach afterward without guilt.

Here are the 3 questions I ask myself:

1. Who am I now?

Not who you were 2 years ago. Not who you think you should be. Who are you right now? What lifestyle do you want? What pace feels sustainable? What do you value most at this moment in your life?

When I started my business, I was in fitness. I had tons of energy. I wanted to see people all the time. But now I'm much more introverted. I've discovered I don't love working 1-on-1, but I thrive in group settings. I don't want to work evenings and weekends anymore. My relationship and my health matter more to me than another revenue milestone.

Your business can't adapt to who you are now if you never tell it.

2. What do I actually want?

Be honest here. Not what sounds good. Not what your coach told you. Not what will make your parents proud. What do you actually want your days to feel like?

Do you want deep work and silence? I love coaching, but if I'm surrounded by people every day with back-to-back calls, I can't hear my own voice anymore. I've learned I want a maximum of 2.5 days with people and 2.5 days alone for creative work.

Do you want to work with people or alone? Do you want a workspace or work from anywhere? How do you feel about 1-on-1 vs. group work? Do you want a small team or a big team?

3. Why did I start this?

This is the question most people avoid because the answer makes them uncomfortable. You started your business to spend more time with your kids, but you're missing bedtime every night. You started it for financial freedom, but you're working more hours than you did in your 9-5. You started it for flexibility, but your calendar is more rigid than ever.

Does your current reality reflect the reason you started? If not, your values are out of order.

The 5 Freedom Levers You Can Pull Right Now

When you identify the mismatch between who you are and what your business demands, you don't have to blow everything up. You just need to adjust one of these 5 freedom levers:

Offer Freedom: What you sell and how often you sell it

Delivery Freedom: How clients get results without you being available 24 hours

Calendar Freedom: How your week is structured and whether you're batching your time

Team Freedom: Who owns what so you stop being the human FAQ

Nervous System Freedom: Creating a business model you can sustain without burning out

Pick the biggest mismatch and fix that first. For me, it was batching. I could easily spend my entire week recording 1 podcast, doing 1 client check-in video, and managing my team. But when I batched all my podcast recordings into one day and all my team check-ins into 1-2 days per week, I got so much time back.

You don't need to change everything at once. Just start with the lever that will give you the most freedom in the next quarter.

Your 15-Minute Quarterly Reset

Here's your homework. Open your calendar. Look at the last 2 weeks. Answer these questions:

  • What gave you energy?
  • What drained you?
  • What are you doing that someone else could do?
  • What are you doing that you shouldn't be doing at all?
  • What one change would buy you the most freedom in the next quarter?

Make one decision. Put it in your calendar. Maybe it's blocking off Monday mornings. Maybe it's moving all your meetings from afternoon to morning. Whatever it is, design your freedom instead of hoping for it.

Download the free Ideal Week Template that includes a full ChatGPT prompt to help you build a schedule around your energy, your values, and the life you actually want: http://fastforwardamy.com/weekplanner

Download the Ideal Week Template
Listen to the full episode

Filed Under: Blog Tagged With: BLOG, BUSINESS, podcast

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