You're showing up, doing the work, leveling up in your business. But when you open your closet, nothing feels right. You know how you want to look but you can't seem to pull it off. And that gap between where you are and how you're showing up is taking up way more mental energy than it should.

Jessie Spressart was in that exact spot. She was already a highly visible leader, speaking and traveling and building Optia Consulting. But her style was stuck somewhere around 2018 and she kept thinking she should be able to figure this out herself. When she finally let go of that and asked for help, everything shifted.

In this episode of The Visibility Shift, Jessie shares what that dissonance actually felt like, why blending in felt safer than standing out, and what changed when she stopped trying to DIY her style. She also gets honest about body changes in midlife and why she decided she deserved to feel good in her clothes no matter what.

3:41 – The subtle exhaustion of feeling “almost there” every time Jessie got dressed

8:58 – How body changes became an invitation for Jessie to honor herself

12:13 – Why high-achieving women struggle to ask for help with something that feels vulnerable

15:37 – How Jessie knew we were on the right track (despite her nerves)

19:42 – The importance of doing the background work before the shopping begins

22:47 – The inherited rule Jessie carried regarding attracting attention

26:47 – How Jessie felt when she incorporated a bit more of herself into her style

29:35 – Why buying the “right” outfit is not the same as doing the internal work

33:24 – The energy cost of blending in and the unexpected ease that comes with congruence

35:04 – How “fake it till you make it” influences your energy when your style is authentic

39:45 – How Jessie caught herself slipping back into old thought patterns at a recent event

42:36 – Jessie’s final words if you’re feeling stuck or worried about making a change

Mentioned In How Jessie Spressart Went From Blending In to Being Herself

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You know something needs to change, but you don’t yet know what. It’s not dramatic. It doesn’t arrive with clarity, confidence, or a five-step plan. It arrives as restlessness, as friction, as the creeping sense that what used to work no longer does.

So you sit in that uncomfortable middle. Not at the beginning of a bold makeover and not at the triumphant reveal, but in the quieter moment where you’re resisting the urge to force momentum just to feel productive. And in a culture obsessed with reinvention narratives and overnight transformations, that in-between space can feel like failure.

In this episode of The Visibility Shift, I'm challenging the idea that change has to be fast, visible, or impressive to count. I make a case for something far less marketable and far more effective: small, intentional actions taken before clarity arrives. You’ll discover what it means to trust yourself when the vision hasn’t fully formed yet, why rushing to “figure it out” often leads you further from alignment, and how slowing down, asking better questions, and making subtle shifts can create more lasting transformation than any dramatic overhaul ever could.

2:04 – Why the pressure to have a “big plan” may be the very thing blocking your next move

4:57 – How trust is the real requirement for meaningful change

7:57 – The overlooked reason style change feels so overwhelming (and how to soften it)

13:27 – The first step you can take to start walking down a new path

17:15 – Subtle ways your closet reveals who you’re trying to be for others

19:51 – Small changes you can make today to start to course-correct

Mentioned In Why Small Steps Are Not Insignificant When You're Ready to Change

The Style Mindset Reset Free Download

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As a speaker, leader, or entrepreneur, your evolution doesn't happen behind the curtain. You don't get days off from showing up while you figure things out. But there's a phase of growth we don't talk about enough—when you know something is changing, when an old version of you has been left behind, but the new version hasn't fully taken shape yet.

The temptation during this time is to hide until everything is perfect. To wait until you have all the answers before you show up for that speaking gig, that client call, that public moment. But that waiting actually delays your progress and keeps you stuck.

In this episode of The Visibility Shift, I'm talking about the messy middle. Why it feels so uncomfortable when you're visible. And why showing up imperfectly through the transition is actually what gives you clarity.

1:51 – Quiet fears that surface when clarity is delayed and what they’re trying to protect

4:03 – The temptation to retreat into a style or persona that once worked but no longer fits

4:44 – The unfortunate truth about the transitional waiting period

6:22 – How I’m living in this in-between season and the biggest lesson learned from it

7:46 – Why your next-level self won’t arrive in a single leap

8:43 – The mindset shift to turn the messy middle from something you dread into something you value

10:33 – The role of style in supporting a deeper internal transition that goes beyond the visuals

Mentioned In When Your Style Is Changing But You Still Have to Be Visible

The Visibility Edit

Standout Style Kick-Starter

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