Connect the dots

“Our website is an embarrassment.”

A recent prospect said that like a criminal confession.

I mean, yeah, the colors were dated. The layout screamed “2018 template” … because that’s (literally) what it WAS.

I felt their shame. Like being forced to revisit awkward yearbook photos. And honestly, I’ve been there too.

Our first logo was, ummmm … a lot. 

Purple and orange. With gradients, shadows, and bevels. Very MacWorld 2005.

But ya know what?

That old logo wasn’t a mistake. It was 100% right for who we were — at the time we launched it.

Just like your early website was right for where you started.

It did the job and told your story at that stage. And every lead, sale, and conversation it generated was one of the “dots” on the path to where you are today.

***

Branding, marketing, website, design … it can’t be a one-and-done effort.

It’s about evolving. 

The voice you found after years of client feedback …
You couldn’t have scripted that at the start.

The UX changes you made after tracking user behavior …
You couldn’t have predicted that in a wireframe.

When you look back, you can clearly see the stepping stones. All the strategic choices that make you a more confident businessperson today.

The key is viewing those milestones through an objective lens.

When you critique your branding, don’t just ask, “Do I still like it?” Instead, ask questions that connect past to present.

1. Does it tell the right story?
   Your visuals, tone, and content should reflect your business now, not what it was when you first launched.

2. Does it speak to your ideal audience? 
   If your clients have evolved, your brand message needs to address their current goals and needs.

3. Does it work in today’s landscape?
   Design trends, tech standards, and marketing channels change. Almost overnight. An outdated website that’s slow to load and lousy on mobile will definitely impact what people think about your business in 2025.

4. Does it feel consistent?
   Website, social, email, print — if they feel like distant cousins instead of family, it’s time for realignment.

5. Are you proud to share it?
   If you hesitate to hand out your business card or send someone to your website, that’s your gut telling you it’s time for an update.

You shouldn’t be embarrassed by the early version(s) of your brand. After all, it’s the reason you know enough to want something better.

The goal isn’t to pretend the early years didn’t happen.

It’s to make sure the dots you’re adding NOW enhance the big picture.

Power Prompt

AI is great at pattern-spotting; when you give it the right questions, it can help you see your brand from a fresh angle. This prompt uses the five re-evaluation questions from earlier to help you reflect without losing sight of your history.

PASTE THIS AI PROMPT:

You are a perceptive brand critic with a knack for spotting what works and what’s out of sync. I’ll share my current brand elements (logo, colors, website link, tagline, sample copy) and describe my ideal audience.

[ Share your reference ]

Using these five questions, evaluate my brand:

1. Does it tell the right story?

2. Does it speak to my ideal audience?

3. Does it work in today’s landscape?

4. Does it feel consistent?

5. Should I be proud to share it?

For each question, give me a short, constructive analysis.
 

Cold emails don’t have to feel gross.

Most people hear “cold email” and picture a sweaty handshake from a stranger on a city bus. [ You’re welcome. 😜 ]

But you’ve probably sent them without even realizing it …

That friendly DM to a podcaster? Cold email.

That intro request to a friend-of-a-friend? Cold email.

The problem isn’t cold emailing. It’s doing it badly.

Stiff, jargon-heavy, desperate messages are just awkward for everyone.

But what if your cold emails felt like handing a neighbor a plate of warm cookies? [ Uh, yes please! 🍪 ]

That’s what my friend Laura teaches in her Feel-Good Email Profit Kit. How to write messages people want to open (and actually respond to).

Lucky for you, I talked her into giving you free access. Thank me later. Preferably with cookies. [ 😉 ]

Grab Laura’s Feel-Good Email Profit Kit

If you’re ready, here’s a few ways we can work together:

Virtual Coffee

Want a website that converts casual browsers into clients? Let’s talk. In just 15 minutes, I’ll tell you exactly what’s holding your brand back — and how to fix it.

One-on-One Deep Dive

Ready for real transformation? Let's spend 60 minutes together, working on your biggest marketing challenges; complete with a customized, actionable roadmap for growth. Ideal for entrepreneurs who are done waiting on "perfect."

Booked by Design

Our 60-day, done-for-you branding & website program to attract high-value, ideal clients. No stress. No tech. No homework. Let us tackle the strategy, tools, and setup so you can focus on what you do best — running your business.