Real Time Creator | A Career Break Diary – Details, episodes & analysis

I’m still REELING over this. Airbnb invited me to fly to San Francisco for an all expenses paid experience at their headquarters for their 2026 Summer Release.

This is far from a play-by-play. I’m taking you behind the scenes of the most interesting aspects of this trip, what surprised me the most, the people I met, and why this brand activation meant SO much more than a free flight.

In This Episode:

• A reality check that had me questioning everything and feeling defeated
• How the Airbnb team caught me off guard (in a good way) 
• The 2 Airbnb stays (out of 100) that didn't exactly go as planned
• What Airbnb got right about hospitality, community, and making people feel seen

Resources & Links:

Watch the 2026 Airbnb Summer Release Event on YouTube (I was in the audience!)

Let's Connect:

Follow me on Instagram: @alisonkinsey or send me an email: alison@alisonkinsey.com. 

Connect with Alison on LinkedIn.

I also help entrepreneurs and thought leaders launch and grow their podcasts through my boutique podcast editing agency, Podcasting for Creatives. 

A very unexpected invitation pulled me across the country, so here I am, popping in from my hotel room in San Francisco.

This episode will feel like a spontaneous, casual voice note, but we’re also talking about opportunities… and how you can create more of them if you just send the damn email!

In This Episode:

• The email draft I sat on for WEEKS and what happened when I finally hit send
• Carly Valancy’s reach out experiment and her overall success rate 
• What exactly led to me getting a mysterious invite to San Francisco
• The deeper fear that hides underneath the possibility of rejection

Resources & Links:

Follow Carly Valancy on LinkedIn and check out her Substack article where she shares more about her Reach Out experiment.

Let's Connect:

Follow me on Instagram: @alisonkinsey or send me an email: alison@alisonkinsey.com. 

Connect with Alison on LinkedIn.

I also help entrepreneurs and thought leaders launch and grow their podcasts through my boutique podcast editing agency, Podcasting for Creatives. 

There is a WILD cultural shift happening between AI, massive layoffs, and the boom of portfolio careers, “boring” businesses, and complete identity rewrites are happening EVERYWHERE.

One woman left Slack and Asana and built a 6-figure income without a traditional job. Another started a “boring” business and had a four-figure day. People are walking away from a stable corporate path to make a zig-zag pivot into a dream they can’t ignore.

It feels less like rebellion and more like recalibration, and I can’t stop paying attention!

In This Episode:

• The unconventional income mix behind Maggie’s $107K portfolio career
• How Alyssa turned a playful hobby into a creative income stream
• The sentence my friend said about her wine bar dream that gave me chills
• My friend’s “boring business” that is generating real revenue
• Why I’m constantly turning to my 80-90 year old self for wisdom

Resources & Links:

Many of the women featured in my stories have Substacks where they go deeper on their pivots! Check them out here:

Feeling Free by Maggie Blackburn

Made of Memories by Alyssa Mopia

From the Inside Out by Jessica Howell

Episode 6: I Turned Down TWO 6-Figure Job Opportunities - Am I Crazy?!

Let's Connect:

Follow me on Instagram: @alisonkinsey or send me an email: alison@alisonkinsey.com. 

Connect with Alison on LinkedIn.

I also help entrepreneurs and thought leaders launch and grow their podcasts through my boutique podcast editing agency, Podcasting for Creatives. 

This is a transparent, behind-the-scenes look at my first 30 days of podcasting. I’m spilling the download numbers, the unexpected surprises and freak-outs, and how putting my “journal” out in the world is already opening doors I didn’t even pitch for.

In This Episode:

• The exact mental block that made YouTube feel impossible even though I had ideas ready to go
• How many downloads I expected to get, vs. how many I actually got
• Why a podcast felt “frictionless” compared to YouTube and what got me to actually hit record
• The 4 things that are still “keeping me up at night” about this podcast

Let's Connect:

Follow me on Instagram: @alisonkinsey or send me an email: alison@alisonkinsey.com. 

Connect with Alison on LinkedIn.

I also help entrepreneurs and thought leaders launch and grow their podcasts through my boutique podcast editing agency, Podcasting for Creatives. 

Two weeks ago, I seriously questioned ending my career break.

In this episode, I’m walking you through what actually happened when I was invited to explore two sales roles I would’ve jumped at a year ago.

In This Episode:

• Why being wanted and “in demand” messed with my head more than I expected
• The bargaining spiral and pros/cons list I went through
• Where I got starry-eyed about saying “yes”, and what it would have meant for this season of my life
• The uncomfortable truth this choice surfaced about my values

Let's Connect:

Follow me on Instagram: @alisonkinsey or send me an email: alison@alisonkinsey.com. 

Connect with Alison on LinkedIn.

I also help entrepreneurs and thought leaders launch and grow their podcasts through my boutique podcast editing agency, Podcasting for Creatives. 

3 years ago, our podcast editing business scaled beyond our wildest dreams to 22 clients. And then my husband ended up in the ER.

Steve is joining me for an honest conversation about how we divide roles, why our dynamic as business partners actually works, and what happened when the overwhelming tension built as our business expanded.

We also talk about juicy things like the moments we annoy each other, the decisions we avoided WAY longer than we should have, and the questions we’re sitting with about ambition, scaling, and health.

In This Episode:

• The exact numbers $$$ of what we made in our first year
• How we went from “fake it till you make it” to 22 clients FAST, without social media
• The terrifying wake-up call that made us downsize, and why it took me over a year to feel safe rebuilding after
• What’s keeping us up at night as entrepreneurs and why we’re happier being a leaner business 

Resources & Links:

Our favorite to-do list/project management tool is Asana.

Thinking about starting a podcast? Fill out this quick form and let’s chat.

Let's Connect:

Follow me on Instagram: @alisonkinsey or send me an email: alison@alisonkinsey.com. 

Connect with Alison on LinkedIn.

I also help entrepreneurs and thought leaders launch and grow their podcasts through my boutique podcast editing agency, Podcasting for Creatives. 

My energy is giving me WAY more information than my to-do lists ever did.

What happens when I stop forcing decisions and start collecting clues? I’m back from a 3-city trip and we’re covering it all: networking, my unexpected obsession at the Tampa RV Show, and a realization about commitment that caught me off guard.

There’s a clear thread in this episode: paying attention to what lights me up, what drains me, and what my body and mindset are trying to tell me.

In This Episode:

• Why I’m not forcing outcomes and focusing instead on patterns, surprises, and signals
• A simple, but powerful language shift from an Entrepreneur Success Series event that felt like a gut punch
• How walking 20,000 steps a day in San Francisco revealed some of my own self-imposed limits

Resources:

Noovo Vans

Entrepreneur Success Series - if you’re local to San Diego, check out Jaymie and Jess’s monthly events for founders

Let's Connect:

Follow me on Instagram: @alisonkinsey or send me an email: alison@alisonkinsey.com. 

Connect with Alison on LinkedIn.

I also help entrepreneurs and thought leaders launch and grow their podcasts through my boutique podcast editing agency, Podcasting for Creatives. 

I hate to admit this, but being on my phone is literally a part-time job. And I didn’t realize how much it was costing me until I looked at the data. (And yes, I’m sharing my REAL screen time stats in this episode that make me CRINGE).

You'll hear what I’m experimenting with, what I haven’t figured out yet, and why this feels like a pivotal moment in my career break.

In This Episode:

• The unexpected question my therapist asked that made me realize I’m not living my ideal “normal” day
• My real screen-time stats, including how often I pick up my phone
• How nighttime scrolling is sabotaging my mornings, routines, and self-trust
• The idea of “putting your phone to bed” and the intriguing tool I’m considering buying 

Resources:

Learn more about the Brick (I’m really thinking about getting one!)

Let's Connect:

Follow me on Instagram: @alisonkinsey or send me an email: alison@alisonkinsey.com. 

Connect with Alison on LinkedIn.

I also help entrepreneurs and thought leaders launch and grow their podcasts through my boutique podcast editing agency, Podcasting for Creatives. 

We’re talking MONEY, baby! Today I’m walking you line by line through all the expenses I cut out of my budget to afford my new life on a creative career break, and the moment I realized that wanting to panic-sell my house wasn’t really about the house at all.

This solo episode is all about what happens when your sense of safety gets shaken, your identity cracks open, and your nervous system starts looking for control anywhere it can find it.

In This Episode:

• The lightbulb moment that stopped me from blowing up my life, and what it taught me about uncertainty
• Exactly how I cut over $1,500 a month from my budget, including the expenses that used to make me feel “successful”
• Why stretching my severance (and paying myself monthly from it) is giving me nervous-system safety 
• A pep talk for anyone experiencing an “in between” phase, a career pivot, or ANY unknowns

Resources & Links:

Episode 1: I Lost My $200K+ Tech Job… and Everything I Thought I Wanted

Save $$ with Mint Mobile - this is my refer-a-friend link

Let's Connect:

Follow me on Instagram: @alisonkinsey or send me an email: alison@alisonkinsey.com. 

Connect with Alison on LinkedIn.

I also help entrepreneurs and thought leaders launch and grow their podcasts through my boutique podcast editing agency, Podcasting for Creatives. 

I thought I had “made it.” Five years into a dream sales career in tech, earning over $200K a year without a college degree, it felt like my life checked all the boxes. But then I got laid off. 

And instead of freaking out and applying to 100 jobs, I decided to treat this as an invitation to start a full-blown creative career break. 

In this first episode, I’m walking you through the emotional unraveling, and the surprising shifts in my body, stress, and creativity that have unfolded in just five months. 

If you’ve ever wondered what a career break can do to your identity, ambition, and sense of possibility, this is the raw, real, behind-the-scenes starting point of my story.

In This Episode:

• What it was like to be a high-earning breadwinner, the lifestyle upgrades I loved, and the downsides that it cost me
• My pattern of shelving my own ideas to work behind the scenes for 7-figure creators 
• The expensive coping ritual I created to escape stress multiple nights a week after work
• The surprising changes that unfolded after my layoff (both mental + physical), and how wildly different my life feels, 5 months in

Let's Connect:

Follow me on Instagram: @alisonkinsey or send me an email: alison@alisonkinsey.com. 

Connect with Alison on LinkedIn.

I also help entrepreneurs and thought leaders launch and grow their podcasts through my boutique podcast editing agency, Podcasting for Creatives.