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Today’s episode is one of my absolute favorites because it’s all about YOU. We’re diving into another Ask Me Anything: your real, unfiltered questions, straight from the Goal Digger community.
Every time I do one of these episodes, I’m reminded why I started this podcast in the first place: you.
You show up with your curiosity, your honesty, and your desire to build a business that doesn’t just look good on the outside, but feels good on the inside, too.
In this special Ask Me Anything episode, I’m answering real voicemails from listeners just like you. We’re talking through some seriously powerful questions: from how to get more organic podcast reviews and build out your content strategy, to navigating grief, mental load, and career pivots with intention.
I even open up about my biggest business failure, and one of my most embarrassing business moments (yes, Facebook status updates were involved!).
Whether you’re starting out or scaling up, I have a feeling something in here is going to speak directly to where you’re at. Let’s dive in!
How to Get More Organic Podcast Reviews
Michaela from Michigan asked how to encourage more people to leave genuine podcast reviews, and I love this question because reviews do matter. Beyond boosting rankings, they’re fuel for creators.
I shared how I used to read reviews live on air, which made listeners feel seen and inspired more people to leave them. I also recommend recording a screen-share tutorial to show exactly how to leave a review (you’d be surprised how confusing it is for some folks!).
The key is to make it about community, not about you. Invite your audience to be the hero by helping more amazing people like them find the show, and don’t be afraid to incentivize in a meaningful way. A valuable freebie in exchange for a review? Win-win!
Batch Working, Rhythmic Content, and Systems That Scale
Ashley from Fort Myers wanted to know how I plan and balance my content strategy, especially when you’re new and juggling a lot (with or without clients!). My biggest tip? Batch work e-ver-y-thing!
Whether it’s email content, blog posts, podcast episodes, or social, batching allows you to take a bird’s-eye view of your content, which helps it make sense and work together more cohesively.
We build a monthly “skeleton” of content, deciding what goes out, when, and where, and then fill in the pieces based on goals or promotions.
Whether you’re solo or have a team, systems like Monday.com (my fav!) or even a simple spreadsheet can help you rinse and repeat your process in a way that feels sustainable and stress-free.
My Most Embarrassing Business Moment (Still Makes Me Cringe!)
Kaeli from Tacoma brought up a fun one: what’s an embarrassing business moment I still laugh about? Let me just say: Facebook-era Jenna was doing the most.
I used to post every time I got a new camera lens, like it was a baby announcement, and I even DM’d people who got engaged with a full wedding pitch (using a saved template).
Cringe? A little. But it also showed I was bold, scrappy, and proud of what I was building.
Looking back, it’s a reminder that we could all be a little more unapologetic about sharing what we do, because if you’re not excited about it, how can anyone else be?
How to Pivot from Service Provider to Passive Income
Misha from Maryland asked how to transition from being a service provider (in her case, a hair and makeup artist) to building a business that doesn’t require constant client-facing hours. I’ve been there!
I walked through three potential pivots for Misha:
1. Creating digital products or courses from your current expertise.
- Why it works: You’re already answering questions and teaching 1:1… this just multiplies that effort and makes it evergreen.
2. Building a team or agency model to delegate client work.
- Why it works: You’re still in your zone of genius, but you remove the “you only get paid when you show up” piece.
3. Funding a new dream (even something outside your current niche) using the revenue from your service-based work.
- Why it works: You’re still earning from what you do now, but using it to build future freedom.
Passive income takes work up front, but building toward time freedom is possible and you get to define what that looks like! Best of luck, Misha!
Breaking the Content Creation Hamster Wheel
Lauren from South Carolina asked how to stop spending all your time creating and start promoting more effectively. It is SUCH a good question!
The truth is, you probably don’t need to create more… you need to use what you already have more strategically. One great podcast episode or blog post can become a week’s worth of content if you extract the big idea, a standout quote, or a tip and tailor it for different platforms.
Think of it like giving your best content a wardrobe change… you can dress one message differently for each platform. For example:
- Your podcast episode or YouTube video is the deep dive
- Instagram might be a quote graphic or reel
- Your Email and blog are spaces for personal storytelling or actionable takeaways
- LinkedIn gets the thoughtful, professional angle
- Pinterest helps drive long-term traffic to your blog with visual pins
The key is to shift from “creation mode” to “distribution mode.” Then, make it easy on yourself with a repurposing system and stop starting from scratch.
Use a content tracker (like Notion or even a Google Sheet) to keep tabs on where your content has been shared. Batch this process by setting aside just one hour a week to break your long-form content into smaller bites.
And don’t forget that AI tools like ChatGPT can help repurpose your content, too!
And if you can swing it, bring on light help, like a virtual assistant or intern, who can repurpose that content for you. You created it for a reason, so give it the lifespan and reach it deserves!
Behind the Scenes of My Personal Struggles
Kristi from Nashville asked what I’m struggling with right now, and it’s a big one: the mental load.
Right now, I’m in the “sandwich generation” where I’m raising young kids while also caring for aging grandparents and it really has been emotionally and mentally taxing.
Balancing business, motherhood, grief, and life’s invisible to-do list has been a challenge I didn’t expect at this level. If you’re feeling maxed out or unseen in this season of your life, know that I see you, and I’m walking through it with you.
My Biggest Career “Failure” (And What It Taught Me)
Jachrisha from Montana asked about my biggest failure and the truth is, while I’ve had plenty of mess-ups, I try not to label them as failures.
One vivid memory? Accidentally erasing part of a couple’s wedding photos.
It was absolutely hut-wrenching, but their grace taught me more than any course or mentor ever could.
Those moments taught me systems, backups, empathy, and how to own my mistakes. So, maybe failure is just the tuition we pay to learn what matters most?
Rebuilding Joy After Loss
Rachel from Louisiana asked how to rediscover the joy in her business after pausing everything following a miscarriage.
First, Rachel, I see you and I’m so sorry. I have shared my own experience with miscarriage on the podcast before, and I know that it shaped not just my business, but my heart.
Instead of rushing back to “how it was,” ask yourself: What does joy look like for me now?
Maybe it’s peace, maybe it’s curiosity. Start small, and write just for you. Connect with past clients without pressure. Let your creativity reemerge slowly, and know your business will wait for you.
When you’re ready, it’ll be even more powerful because you’re bringing your whole heart with you.
Your Voice, Your Questions, Your Show
As we wrap up, I just want to give a big shoutout to everyone who called in and shared their heart, their challenges, and their curiosity with me!
These Ask Me Anything episodes remind me how powerful our community is, and how many of us are navigating similar questions, just in different ways.
Whether you’re focused on growing your audience, shifting your offer, or building in a way that supports your life (not just your business), I hope today gave you some clarity and encouragement.
Got a question you’ve been dying to ask? Call me at 218-203-9660 and leave me a voicemail. Your question just might be featured on a future episode of the Goal Digger Podcast!
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