Episode 99: Best-Of Here’s What I Learned

As I wrap up Season 9 and look ahead to Season 10, I wanted to do something a little different — a mixtape of the moments and ideas that still shape how I think about work, rest, and doing business differently.

These clips remind me why I started Here’s What I Learned in the first place: to have honest conversations about what’s working, what’s not, and how we can build businesses that actually fit us.

You’ll hear from some of my favorite past guests whose lessons keep coming up again and again:

• Becky Mollenkamp on how “professionalism” is often code for control — and why it’s worth breaking those rules to make your business more you.
• Amanda Gold on turning work into play with her D&D dice, using small rolls to gamify focus and motivation.
• Patricia Sung on designing for energy, not just time — with white space, buffer, and cycle-aware planning that makes business sustainable.
• Steph Wharton on flipping goal-setting upside down: start with the life you want, then build the business that supports it.
• Tracy Stanger on doing the weird stuff only you can do — and keeping your plans simple enough to survive real life.

Because business isn’t a perfect playbook. It’s a living experiment.

Topics:

• Why “professionalism” often limits creativity — and how to rewrite those rules
• The power of tiny experiments and joyful data
• How to plan for energy, not just time
• What it looks like to reverse-engineer your business from the life you want
• How simplicity protects creativity (and sanity)

Mentioned in the episode:

• Ditching ‘Professionalism’: How Work Norms Hold Us Back with Becky Mollenkamp
• Rolling Dice & Making Business Fun with Amanda Gold
• Failure is Required with Patricia Sung
• Goal Setting for a Whole Damn Vibe with Steph Wharton
• Do the Weird Shit Only You Can Do with Tracy Stanger

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Credits:

Intro and Outro Music: Atomic by Alex-Productions |https://onsound.eu/

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Creative Commons / Attribution 3.0 Unported License (CC BY 3.0)

Transcript

Jacki Hayes

Hey there, welcome to Here's What I Learned. I'm Jacki Hayes, a system strategist, unapologetic, smutty romantasy lover, Dungeons & Dragons geek, and your no-BS guide to building a business that works for you. This is the place where we swap stories, share lessons, and get real about the highs and lows of creating a life and business that actually feels good.

No cookie-cutter advice here, just honest conversations about what's working, what's not, and how to rewrite the rules to fit your version of success. So grab your favorite beverage, get comfy, and let's dive in. Hey friends, welcome to episode 99 of Here's What I Learned.

Before we do anything else, I want to say thank you. Over the years, nearly 60 guests have shared time, stories, and hard-won lessons with us. Some were friends before they came on the show, many have become friends and collaborators after.

I'm grateful for every one of you. When I started this podcast back in March of 2021, the goal was simple and very me. Talk to more people, learn from more people, and build deeper relationships through honest conversations.

Mission accomplished and still ongoing. It wasn't always easy. Producing a podcast solo is a lot.

It's time-consuming, it's fiddly, and there are moments you want to set the whole thing on fire and walk away. The season format is probably what kept this show alive. Built-in pauses to breathe, learn, and come back better.

And now, I'm even happier to say I'm not doing it alone. PodFox Media is producing the show, which means they handle the parts I hate doing, and I get to focus on conversations, ideas, and making this genuinely useful for you. So PodFox, you're the best.

So what's coming next? January kicks off Season 10 of Episode 100, and we're doing something I'm really excited about. Experiments. Here's how that'll work.

We'll design a small, real-world experiment around a business question, something a guest is actually prescribing to me. We'll document the setup, the constraints, and what success would look like. We'll run it, check the data, and talk honestly about what happened, what worked, what didn't, and what we would do differently.

And these are experiments you can follow along with and do yourself. Because running a business is running experiments. We're always learning, iterating, and choosing the next right step with the info we have.

I want the show to reflect that reality. Less perfect playbook, more let's test this out in the wild. And don't worry, we're keeping the in-depth interviews you've told me you love.

You'll still get thoughtful, long-form conversations. The difference is you'll also hear the process of testing ideas, not just the polished outcome six months later. If you're the kind of listener who hears this and thinks, ooh, I have an experiment I want to try, I'd love to hear about it.

Bring me your hypothesis, your constraints, your messy middle. That's all the good stuff. To our guests, past and future, thank you.

To PodFox, thank you. And to you listening, thanks for being here, learning alongside me, and making it possible to reach episode 99. Season 10 lands in January.

We're going deeper, we're getting braver, and we're treating business like the living lab it is. All right, let's get into today's episode. Today, we're doing something a little different.

I pulled the moments from past episodes that still hit home. Think of this as a highlight reel of ideas we keep returning to. Doing business your way, not the quote-unquote professional policies and policing.

Design for energy, not just time. And treat business like a series of small experiments you learn from. Okay, so we're going to jump right in.

First up is Becky Mollenkamp from Season 8. We talk about how professionalism can be code for control, and why building a business that is deeply you is the point, not the problem. 

Becky Mollenkamp

Who established what is and isn't professional? It was white men, right? Because for the bulk of modern history, post-industrial history, it has been white men in the workplace. Obviously, long before that, women were very much involved in work and in labor, but we were not paid for our labor.

We continue to not be paid for a lot of our labor as caretakers and parents, but we were not paid for our labor and contributions, or it wasn't valued the same way. But the move to the office space, and that was the biggest piece of that post-industrial moving to the office space, and white men were the ones who were first just even allowed to work. And then once women were allowed, quote-unquote, to come into the workspace, it was still the white men who were determining what was and wasn't acceptable in the workspace.

And so, of course, the goal was to make everyone as white and as male as possible, whether you were white or male or not, right? So the idea of a suit, and how long did it take for people to say, why do I have to wear a suit? And women wearing suits, and what do their suits need to look like? And women needing to wear hosiery for the longest time. And anyway, and you're right, absolutely the things that continue today around, what does a person's hair look like? Who is to say what is professional as far as appearance? And then also behaviors, because it corrects for language, right? There's only certain types of language that are professional, right? There's only certain relationships with time that are professional. So it's like in all parts of the way we show up in work, and trying to question ourselves around those.

And to be clear, some of those things you may find work really well for you, right? Some people being able to get work done looks like having an office, or it looks like having a desk, or it looks like working between set number of hours, right? Because of childcare restraints. Like there are things that are traditionally quote unquote professional, you may continue to adopt because they work for you. But that's the key thing going to your idea of like, what does it mean to work for you? It's like, it needs to work for you, right? And there are times for me when including right now, working my desk doesn't work for me.

So I'm not working at my desk. Am I less professional? Am I not able to accomplish my work? Am I not able to show up and speak to your questions? No, right? So why should it matter where I'm performing the job as long as I'm able to do the job and do it well. But those were things that were hard for me to break for a long time.

And I think they are for most people. And I think the big thing is most of it goes unexamined for most of us. We just assume that that is the way it has to be because it's just what we've always known.

And I think the exciting part is when you can finally start to question it all and say, why? Why do I think it has to look this way? What changes if I say, I don't like that. I want to do this instead. Does that really affect my performance? Does it affect the results? Maybe not.

Jacki Hayes

If professional ever made you smaller, that's your nudge. Values over vibes over rules. Staying with Becky for one more.

This is the quote, unquote, love seat format. One creator in the seat, a whole room of brains supporting, and we start with better questions. I know that the way you're running the quote, unquote, meetings is this love seat idea.

Jacki Hayes

How did that come to mind and what does that look like if you could describe that for the listeners? 

Becky Mollenkamp

Yeah. So just quickly, we have four calls a month. One is a co-working session.

Most people know what those are. We just get together and work on things quietly. One is an education session.

We have an outside speaker come in and teach us something related to podcasting. Then the other two sessions every month are what we call the spotlight sessions, where one podcast is in the love seat, not the hot seat, because that sounds really not fun. So a love seat, who wouldn't want to sit in that? The entire collective brings all of our thinking power together to help that podcaster with whatever challenge they're facing.

It could be something around monetization, like how do I get sponsors, or how do I turn these listeners into clients? It could be something around the content. Is this resonating? What could I do better? I'm running out of ideas. It could be a whole host of things.

It could be administrative stuff. I need better systems in place, or what tools should I use? We all get together and help them with that. Then the week following their love seat session, the whole collective works together to promote their podcast.

Jacki Hayes

The clarifying questions often beat the quick fixes. Curiosity scales better than certainty. Now, next up is Amanda Gold from Season 7. This one's playful.

What happens when you add a game mechanic, like rolling dice, to keep experiments small, safe, and fun? 

Amanda Gold

I love that you asked, because this has been a huge part of making business better for myself. I think I have ADHD too. I've never been officially diagnosed, but I tick all the boxes.

When I started treating myself as such, things have been a lot better. One thing is gamifying stuff. I love dice.

I collect dice. I use them all the time. If there's something mundane or tedious that I know I don't want to do, I'll roll a D6 and a D20.

That gives me anywhere from two minutes to 26 minutes that I'm going to focus on this thing. All my D&D dice are now going to be used in my business, because I absolutely love that. By the way, I also have business-only dice that kind of match my business-only deck.

They're very sparkly and pointy. I have them handy, but they're on my altar over there. Yeah, I have dice for different phases of my menstrual cycle too.

I got red ones. I got hot pink ones. I've got glittery ones.

Also, another thing I'll do is I'll list out six things that I want to get done over the day or the week, and then I roll a D6 to decide which one to start first. That's been really fun. Another way is I'll do a list of ought tos, have tos.

I don't actually believe in should do or have to. Everything's a choice, but taxes would fall on the ought to, have to side. Want to would be like go for a walk, make art, work on a puzzle.

Then I'll roll a dice, and even as I work on this list, odd as I work on that list. And so I'm weaving fun things in with have tos, because when I first started, I was so earnest and diligent and serious that I was only focusing on everything I should be doing to have a successful business. And I've really been able to lighten up and understand the importance of play too.

It really is a non-negotiable to make it fun and make it interesting and give myself treats and rewards along the way as well. Tiny bets, fast feedback, joyful data. That's going to be the Season 10 energy.

Jacki Hayes

Also from Season 7 is Patricia Sung, designing for energy, not just time. White space, buffer, and cycle-aware planning so your business stops fighting your brain and body. 

Patricia Sung

I think even if you're thinking, well, I don't have a regular cycle, or maybe you're a dude listening, you don't have a cycle at all.

This idea of making your schedule fit you doesn't have to hold to this pattern. What is it that's going to work for you? I think all of us would do better with a week where it's just, tone it down a little bit. Let's rest a little more.

Not having all these meetings on your calendar gives you space to work on the big projects that you've been meaning to do for who knows how long, but never got around to it. This idea of not every week has to be the same. I don't have to go 100 miles an hour.

Every week, all day, hustle culture, go, go, go. We don't have to do that all the time. It's okay to take a week and say, even if you have no idea how it relates to your hormones, I'm just going to have a chill week.

I'm going to clean out the thing that I've been meaning to clean out, like your proverbial closet clean out of your business or work on that cool thing. But to have the space to do that, especially if you have ADHD, we need that white space. We need space for our brains to wander and run around and listen to all the cool ideas floating around our brains.

And that wandering white space is so good for you. So even if it's not in time with your body, having that space where a week is different can really be helpful and restful and actually brings you to be so much more efficient because you've had that space to slow down for a sec. Build in more margin than you think you need.

Jacki Hayes

Protect the joy and watch productivity follow. Next we have Steph Wharton from season four. She flips goal setting on its head.

Steph Wharton

Start with the life you want, then reverse engineer the business to support it. So one of the more simple and tangible ways that I like to do that is I have a bit of like an onboarding process. You've obviously gone through it, but for people that haven't seen it, it's essentially a form and we start to uncover what the goals are.

But instead of just asking what your goals are just flat out and allowing that kind of conditioning to come through and the comparison and just these ideas around what goal setting should look like based on what people are used to seeing and experiencing. I like to ask different questions that kind of rephrase the question at hand. So it can be something along the lines of what's your goal in business? Like, is there something you want to launch? Is something you want to achieve? Is there a lifestyle that you want to embody? Whatever.

But then start to reframe by saying things such as stop thinking or focusing necessarily on what other people are achieving, what other people are talking about. So if we're removing the comparison, we're removing what everybody else is doing. What I love for people to start with is what do you want your life to look like? Like best day.

If you were having so much freaking fun, you felt like a total badass, like what does that day look like? And then we can actually work backwards and figure out what kind of business structure, whether it's the offers of marketing, the behind the scenes, support, whatever that could be, how can that actually support that dream lifestyle? So instead of going for the, Hey, I want six figures or, Hey, I want to launch a program or I want this. It's like, well, no, is that actually what you want? Maybe, maybe somewhere in there that's true. And that's a fact, but at the end of the day, that's more from like, let's create impact and let's have a financially sustainable, like a stream of income.

But other than that, the goal for a lot of entrepreneurs usually is more intrinsic. It's more about, I want freedom. I want flexibility.

I want to be happy. I want to do something that I love. I want to call my own shots.

So if that's the goal, then what does that look like in real life? So at the end of the day, whether it's through onboarding, whether it's through ongoing coaching, we try and coax that out. And for some people it's more natural. And for other people, you know what, no, we might go in a certain direction, experience some resistance.

And as we experience that resistance, we start to uncover perhaps the reason why. And maybe the is why they've thought they wanted X, Y, Z. But in fact, when you're looking inwards and trying to explore what makes you happy, it gets to look like something completely different. 

Jacki Hayes

I know when I was filling out the onboarding workbook, one of the things that happened is I filled it out and then I went back to it and I literally have strikethroughs because I'm like, those are not really my goals or whatever it happened to be.

I realized that the conditioning that I saw in that, and I wanted to keep it there. So instead of deleting it, I kept it there and just did the strikethroughs because they're like, I want to remind myself of this. And then I remember we just did our quarterly reviews of our goals and going back and being like, oh, my goals literally started with, I want December off.

I want to take May and June off. Those were my top goals. I want to set up my business so I could have three months out of the year that I'm really working and two additional months that are kind of slow.

So basically I don't want to work full time for half of the year. So those were the top goals I had for my business. And then it was like, okay, well, how do I achieve those? My business now has to be set up in such a way that that's a possibility.

So what does that look like for me? 

Steph Wharton

Yeah. I actually, I'm going to say I loved and appreciated the fact that you left that information there and just crossed it out. Because even for the coach or anybody that's working with you, exposed to you, it's good to have that insight just to see how your brain works.

What was the goal perhaps, whether fully realized or not, doesn't matter. But at one point it crossed your mind. So then that helps the entire process.

If that ever comes back up again, then it's like, huh, we're aware of it. So it's like, okay, let's explore it. Maybe, maybe realistically speaking now it is a goal or is there doubt setting in or is something changing that's making us think we want that again, as opposed to the month off or whatever it else that was like feeling much more empowering and exciting.

Jacki Hayes

I keep my struck through conditioned goals visible. It's an honest mirror and a great filter from season seven, Tracy Stanger with a mantra I love: do the weird stuff only you can do and plan simple enough that it survives contact with real life.

Tracy Stanger

Okay. Well, first of all, I'm so excited that you are asking this question that we're having this topic because I also think that I'm going to minimize this. Like I tried to, if you have seen me for a minute, you know, I'm all about doing what I call most you business.

And so what that really means to me is I believe that everybody has something in you that only you can do the way only you can do it. I really want to see people being creative and doing that weird shit inside of you that only you could do. So I actually, I, it kind of goes back to how I started this business.

I started it to help moms create space in your life, knowing that like momming and business could take up 24 seven. And so I kind of thought this would be time management in quotes, but really the answer for getting things done in less time is focusing on doing things your way. And, you know, over time we have been in this business over five years at this point, it's become even more important to me to kind of combat the traditional business that we see, or the, you know, do it just like me.

Cause I said, and it did, you know, kind of pyramid scheme online business that there is, it's just that much more important to do things your way. So when you do business your way, what does that look like? Well, I mean, hopefully everything that I do, um, and just to clarify, like by business, even I believe that's, it's really just three things. Like you need something to sell, some way to sell it, some way to count your money and keep it coming.

Which in other words is like, you need offers, you need a marketing and sales strategy, a way to meet new people, tell them what you do, build relationships, ask for the sale. And then literally like how you work, do you work in the morning? Do you work every day? Do you work for three hours at a time or 15 minutes? Like all of that stuff. Most me business, like doing business my way is in everything.

The offers that I design, how I meet new people, what I like, what I do, the tools I use, all of it. 

Jacki Hayes

Excellent. So for those of you who've been listening to the podcast, um, for a while now, Tracy has been on the show before.

Um, one of those episodes was a launch lessons episode for the private podcast that is out right now at the time of recording this. By the time you hear this, it probably will not be available. Then also the plan your year episode, we talked a lot about the tool that you have, um, that is plan your year and how it came to be and how you use it.

Can we do just a little teeny tiny recap of that? 

Tracy Stanger

So people get really interested to go back and listen to that other episode. Yeah. So plan your year again, uh, doing business my way thing.

I knew that like, in order to do the things I want to do, I needed to first see what space I had available. So when I started this business, I was still in my nine to five. I had very limited time, probably like 10 hours a week to devote to this business, which I've since stayed at about 10 or 15 hours a week, even with more time.

And so plan your year was born of my process to visualize that, to see what kind of space are we actually working with here? And then a process to walk through, like, what is it that's most important that you're trying to get done? So when are you going to do that with space for this? And it's so, it's a process that walks you through figuring out like when you do what in your business so that you are making the most impactful steps forward. You're weeding out this shit that doesn't need to get done. And it's awesome.

Jacki Hayes

If the plan doesn't fit you change the plan, not yourself. Thank you for listening. And thank you to every guest who shared your brain and your heart on this show.

If one of these moments sparked something, tell me. I want to hear the experiment you're itching to try, the constraint you're working with, or the metric you care most about. Season 10 starts in January.

We're keeping the deep interviews and we're adding small real-world experiments, defined upfront, debriefed honestly. If you've got one in mind, pitch it to me. Bring the hypothesis, bring the messy middle.

Big thanks to PodFox Media for producing the show so I can focus on conversations and what you actually need. If you love today's episode, send it to a friend who'd appreciate a gentler, more human take on business. I'm Jacki, this is Here's What I Learned, and I'll see you in Season 10.

Thanks for hanging out with me on Here's What I Learned. If today's episode gave you an aha moment, a laugh, or something to think about, make sure you're subscribed to my email list. That's where I share even more tips, stories, and behind-the-scenes insights to help you simplify and thrive.

And remember, you get to do business and life your way. Until next time, keep experimenting, keep simplifying, and keep learning.