August 15, 2025

When Your Business Hits a Wall: How to Navigate Separation Season Like a Pro

Podcast Episode: Business Transformation: Embracing Change and Self-Trust

Let me ask you something: Who told you online business was easy? Because if someone did, they lied their ass off.

Right now, I’m in a place in my business where I’m reevaluating everything – my offer suite, my audience, my messaging, my marketing, my branding, my backend systems – all of it. And it’s a natural place to be for business owners, but that doesn’t make it any less overwhelming.

If you’re going through something similar, this episode is for you. We’re talking about what I call “separation season” and why these challenging times in your business aren’t a sign you’re failing – they’re a sign you’re growing.

What the Hell is Separation Season?

I first learned about separation season through Ed Mylett, and it’s become one of the most important concepts I share with entrepreneurs. Here’s the deal: everything in business (and life) goes through seasons.

There will be seasons of:

  • Growth and seasons of loss
  • Momentum and seasons of lull
  • Easy wins and seasons that try every fiber of your being

The “ebb” periods – the tough times – are what we call separation seasons. It’s when the universe separates the good from the great, the committed from the non-committed, the people who are in it to win it from those who just wanted a quick flash in the pan.

During separation season, people quit little by little, even though they’ve committed to building something meaningful. Why? Because they don’t know how to get through tough times in business.

Why Separation Season Will Try Your Soul

When you’re in a season of change, lack of momentum, or challenging decisions, it will push you to your absolute limit. It will:

  • Challenge who you believe you are
  • Test the tenacity you think you have
  • Make you question everything in your life up until this point
  • Force you to make decisions without knowing if they’re “right”

But here’s what nobody tells you: if you weren’t going through that, you’re not actually creating a real business.

Diamonds are created under pressure. I hate cliché platitudes, but this one’s actually true, especially in entrepreneurship.

My Personal Separation Season Story

Last night, I was on my couch in my usual position – feet on my husband Keith’s lap while he rubs them (our nightly ritual), laptop on my lap, working on backend systems and making constant business decisions.

Most people would think this sounds unappealing, but I have my eye on the prize: creating a business that’s automated on the backend while serving people I genuinely give a shit about.

But something was weighing on me, and I started crying. There I was, about to turn 41, sobbing to my husband about where I’m emotionally struggling in my business growth.

The Pivot That Changed Everything

Here’s what was eating at me: Up until now, my ideal client has been beginners – people entering the online world who need foundation skills for content creation, affiliate marketing, or digital products.

But what keeps slapping me in the face is this question: Is that who you really want to talk to in this current season of your business?

What keeps coming up for me is that I have a lot to offer intermediate people. The entrepreneurs who:

  • Have been online for 6 months to 2 years
  • Already know their niche and target audience
  • Understand what a sales funnel is
  • Have decided on the pieces but need to enhance them
  • Need help gluing everything together to make their business grow

When Self-Trust Becomes Your Superpower

As I was sobbing on the couch (shoutout to my husband Keith, who’s emotionally mature enough to sit with me in any state and is the number one fan in the Vicki fan club), he brought such clarity to my situation.

He said, “Vicki, it’s not black or white. You can still help beginners with your foundation education through your courses and self-led community. The people meant for business will move up with you, and those who aren’t will fade away – and that’s okay.”

This hit me like a lightning bolt: The people who are meant to go with you on your journey will. The people who aren’t, won’t. And all of that is perfect.

The Gray Area Where Growth Lives

My brain is so black and white sometimes – it’s yes or no, right or wrong. But Keith illuminated the gray area where I can:

  • Still serve beginners through static courses and community support
  • Light my soul on fire by working hands-on with intermediate entrepreneurs
  • Help people at different levels with different types of support

When it comes to growth, that single conversation was such a breakthrough. It gave me permission to step into a whole new power in my business.

Why Business Evolution Requires Extraordinary Self-Trust

Here’s the thing about entrepreneurship: The journey of business evolution requires an extraordinary level of self-trust. And self-trust is only built and strengthened in moments when you allow yourself to trust yourself.

When you’re going through separation season, you’ll be tempted to look outside yourself for answers. Random course coaches, other entrepreneurs, anyone who might have “the” answer.

But here’s what I’m practicing daily: checking back in and saying, “Vicki, Random Joe Schmo course coach doesn’t know that answer. You know that answer. Listen to your gut. Trust yourself more.”

If You’re Going Through This Right Now

Maybe you’re a beginner who hasn’t started yet, trying to glue the pieces together and create some foundation to move to that intermediate level. Or maybe you’re further along, facing your own business transformation decisions.

Just know this: If you’re going through something challenging in your business right now, you are exactly where you’re meant to be.

Without going through the trying emotional times, without the reevaluation of what you want your life and business to look like, your business will never grow.

Don’t Confuse Growing Pains with Failure

Don’t take tough times or emotional roads as an indication that:

  • You’re not in the right place
  • You’re not good at this
  • You’re not doing it well enough
  • You should quit

These challenges happen in every business. The question is: which side of the separation season spectrum are you going to fall on?

Are you going to be someone who gets weeded out, or someone who uses these moments to build extraordinary self-trust and create something meaningful?

The Bottom Line

Separation season will separate the self-motivated from the externally motivated, the internally disciplined from the flash-in-the-pan motivated. It’s the most exciting time for entrepreneurs, but it’s also the time that tries you every moment.

You’ll be left making decisions without knowing if they’re right. You’ll question everything. But this is where the magic happens – when you learn to trust yourself more than any external voice.

2025 is going to be fucking epic for those of us willing to do the work, make the hard decisions, and trust ourselves through the transformation.

So if you’re in separation season right now, know that you’re exactly where you’re supposed to be. Keep reminding yourself of that, and let’s see what side of the spectrum you choose.


Ready to dive deeper into building your digital empire? Subscribe to Beyond the BS and follow me on Instagram @the_no_bs_newyorker.


leave a comment!

Comments

Leave a Reply

Your email address will not be published. Required fields are marked *

Recently on the blog:

website design by SOULBRIGHT STUDIOS

legal pages

© 2025 Vicki Pollack, All Rights Reserved