The Optimization Toolbox with Jenna Redfield

The Optimization Toolbox with Jenna Redfield VIP Video Day. Notion Education & Resources. Follow me on substack
https://jennaredfield.substack.com

Digital Marketing Strategist and Coach
www.jennaredfield.com & Twin Cities Collective

05/28/2026

I built my own Spotify Wrapped inside Notion using Claude Code — and it actually works 🎵✨

No more waiting until December to see your top artists and songs. With the Spotify API + Notion, you can check your listening stats ANY time of year.

This was my first time using Claude Code and I just asked it what to do step by step. Honestly so much easier than I expected.

What you can do with this setup:
🔁 Auto-update your stats monthly
🎧 See your top artists + songs on demand
📊 Keep your listening data inside your Notion dashboard
🤖 Use AI to build integrations you never thought possible

If you love finding tools that actually make your life easier, you’ll love my free weekly newsletter The Optimization Toolbox — I share the best AI, Notion, and productivity finds every week. Link in bio to subscribe 👇

jennaredfield.substack.com

Genuinely cannot tell you how many networking events I have left thinking — I remember zero names and I talked to like 1...
05/25/2026

Genuinely cannot tell you how many networking events I have left thinking — I remember zero names and I talked to like 15 people.

So when I found out had a whole system for this — and that he once memorized every single person in an audience — I had so many questions.

Turns out the reason most of us forget names isn’t because we’re bad at it. It’s because we never actually heard the name in the first place. We’re so busy thinking about what we’re going to say next that the name just... doesn’t register.

Bob teaches a three step method for fixing this — and it’s way more simple than I expected. You listen, you convert the name into a visual image, and you link it to something on their face. Weird images work better. Your brain loves ridiculous.
He also told me name tags are a crutch (controversial but he’s right), what to say when you genuinely blank on someone’s name, and why remembering someone’s name makes them more likely to remember yours.

Full episode of the Optimization Toolbox podcast is up now — link in bio. 🎙️

Filmed at .online in Robbinsdale

If I told you these photos were from my first headshots 10 years ago this week, would you believe me?Well it’s true! Peo...
05/21/2026

If I told you these photos were from my first headshots 10 years ago this week, would you believe me?

Well it’s true!

People always ask me when my entrepreneurship journey started.

And I always kind of shrug because… I feel like I’ve been an entrepreneur since I graduated college at 22 and started my first business as a wedding videographer two weeks after I graduated.

I’ve always had a side hustle. I’ve always done my own thing.

The last time I had a “clock in / clock out” job was 2018.

Ever since then it’s been clients, consulting, marketing strategy… and now I’m back in my videography era too.

There were slow seasons (hello, COVID). There are still parts of running a business I’m not naturally great at. But I’ve learned a lot.

And I’ve learned this: a 9–5 just isn’t my life path. My brain has made that very clear.

So if you’re in your “should I go for it?” era… here are a few of my 8-years-in lessons:
Pivoting isn’t failure. It’s the job.
Your offer, your audience, your content, your positioning — it’s all going to evolve.

Visibility is a skill. Memorability is the strategy.
Being “good” isn’t enough if nobody knows you exist. The people who win long-term are the people who show up consistently and give people something to remember.

Your offer has to feel like a “no-brainer.”
The easiest selling I’ve ever done was when the offer was so clear and so valuable that it removed hesitation.

Being everywhere works… when it’s systemized.
You don’t need to post on every platform every day. You need a repeatable way to show up where it counts.

Professionalism gets you hired. Personality gets you re-hired (and referred).
People want results, yes — but they also want to work with someone they actually enjoy.

People underestimate how long this takes.
The “overnight success” is usually 5–10 years of showing up

Also: I weirdly love business development. I love networking. I love meeting new people. Some folks love retainer clients— I love the novelty of new projects.
And somehow… I always figure it out. I feel like a cat with nine lives.

If you’re building something right now and it feels slow: you’re not failing. You’re in the part that most people quit.

The last week or so…Art-A-Whirl, Ashley’s birthday brunch, EP Chamber event at The Game Show Studio, Trivia at Bauhaus (...
05/18/2026

The last week or so…
Art-A-Whirl, Ashley’s birthday brunch, EP Chamber event at The Game Show Studio, Trivia at Bauhaus (RIP), Pilates in the Park.
A very busy but fun May so far!

05/14/2026

The number one thing I tell every client right now?

You’re not just making content for people anymore. You’re making it for robots too.

And if you’re not on LinkedIn? AI can’t find you.

LinkedIn is the #2 source feeding AI tools like ChatGPT, Perplexity, and Gemini with information. Every post you write gets indexed and surfaced to people searching with AI right now.
This is why I’m obsessed with Social Search Optimization (SSO) — making your content searchable, not just scrollable.
Here’s what that looks like:
✅ Write keyword-rich captions
✅ Caption every video (most content is watched on mute) ✅ Post consistently
✅ Use words your audience is actually searching for

The creators winning right now aren’t just chasing likes.

They’re building content libraries that work while they sleep.

This is a huge part of what we focus on in my VIP Video Days — creating clips that don’t just look good, but actually get found.

Your content should work for humans AND robots. 🤖

Are you optimizing for both? Let me know in the comments 👇
VIPVideoDay

05/12/2026

Work is broken.

And everyone knows it.

COVID cracked the foundation. AI is finishing the job.

We went home in 2020 and realized — wait. I'm just as productive in my kitchen. And I don't miss the commute. Or the politics. Or the 6 hours of meetings.

Then AI showed up and started doing the tactical stuff. The stuff we were hired to do.

So now everyone is asking the same question:

What exactly is work supposed to look like now?

Remote work was the first answer. Consulting was the second. Freelancing was the third.

But there's a name I keep hearing everywhere right now.

Fractional.

I sat down with John Arms, the "Godfather of Fractional" this week at the PodcastCrew studio in Robbinsdale — thanks to William McLeod and the team for the great space and full episode production — and he broke it down simply:

Full-time right now is hard. Freelancing is unpredictable. Fractional is the sweet spot.

Permanent part-time. Embedded with a client long-term as their expert. Stable income. Work in your zone of genius. No 40-hour weeks.

Most solopreneurs I know are already doing this. They just don't know it has a name yet.

The old model wasn't built for us. Maybe this one is.

Podcast Clip Created & Edited by Yours Truly at Red Thread Studio MN

🎧 Full episode is live on The Optimization Toolbox.

https://jennaredfield.substack.com/

Best place to watch or listen is my Substack — full YouTube video, show notes, and every episode in one place.

If you’ve been trying to get organized in Notion for years and it never sticks… this is for you.Last week at both Minneb...
05/11/2026

If you’ve been trying to get organized in Notion for years and it never sticks… this is for you.

Last week at both Minnebar + the AI Summit, I kept hearing the same thing after my talks:

“Okay but… how do I actually use Notion + Claude when my brain is chaotic?”
So I built the thing I wish existed.

Notion + Claude for ADHD Brains — the first of a new monthly, live Zoom workshop where we build a system your brain will actually use.
No perfection. No “second brain” pressure. Just practical workflows that reduce overwhelm.
Here’s what we’re doing together:
→ Turn brain dumps into a plan you can execute (without getting stuck)
→ Build a content hub Claude can read + help you use
→ Use Claude to pick “today’s priorities” based on your real priorities

Hands-on. Real examples. Bring your mess.

First session: Tuesday, May 13 @ 12PM CST. Just $10 to join. https://luma.com/u319x0l5 or link in bio

Want to come to future sessions? join my Substack for $5/month and get access as part of the membership. https://jennaredfield.substack.com

If you’ve been trying to get organized in Notion for years and it never sticks… this is for you.Last week at both Minneb...
05/08/2026

If you’ve been trying to get organized in Notion for years and it never sticks… this is for you.

Last week at both Minnebar + the AI Summit, I kept hearing the same thing after my talks:

“Okay but… how do I actually use Notion + Claude when my brain is chaotic?”
So I built the thing I wish existed.

Notion + Claude for ADHD Brains — the first of a new monthly, live Zoom workshop where we build a system your brain will actually use.
No perfection. No “second brain” pressure. Just practical workflows that reduce overwhelm.
Here’s what we’re doing together:
→ Turn brain dumps into a plan you can execute (without getting stuck)
→ Build a content hub Claude can read + help you use
→ Use Claude to pick “today’s priorities” based on your real priorities

Hands-on. Real examples. Bring your mess.

First session: Tuesday, May 13 @ 12PM CST. Just $10 to join. https://luma.com/u319x0l5

Want to come to future sessions? join my Substack for $5/month and get access as part of the membership. https://jennaredfield.substack.com/p/i-rebuilt-my-entire-notion-setup

Address

Minneapolis, MN

Opening Hours

Monday 9am - 5pm
Tuesday 9am - 5pm
Wednesday 9am - 5pm
Thursday 9am - 5pm
Friday 9am - 5pm

Website

https://jennaredfield.substack.com/

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