5 years self-employed: milestones, hurdles & honest reflections - Episode 98
Somehow I blinked and it’s been five years since I quit my job in marketing to pursue content creation full-time…which honestly feels surreal to say out loud. Five years as a full-time content creator!
There have been a lot of highs, a lot of lows, and a lot of in-between moments that don’t always make it onto the internet.
In today’s episode, I’m breaking it all down. The standout career moments, the hardest moments you didn’t see, how my business has changed over time, and the biggest difference-makers that have allowed me to actually sustain this for five years.
I’ll also share what I would prioritize if I were starting from scratch today, because the industry looks very different now than it did when I began.
This episode is less about tactics and more about the reality of building something long-term—and what it actually takes to make this work as a career, without millions of followers.
Create & consume:
What Austen is creating this week: my Palm Beach blog post where I share my top recommendations for visiting and the differences between West Palm Beach and Palm Beach
What Austen is consuming this week: I successfully(ish) made homemade pasta for dinner last week! I have to tweak the recipe a bit but it wasn’t bad for a first attempt
In this episode:
The path to self-employment
Before I was my own boss, I spent nearly a decade building a foundation in media and tech.
I started my blog back in 2012 at the same time I started college.
Between 2013 and 2016, I was interning at magazines during every spare moment.
That led into my magazine editor era from 2016 to 2018, followed by a period of freelancing, and eventually a two-year stint at a tech startup.
By 2021, I finally made the jump to my self-employed era!
While I’ve talked about the logistics of my business in episode 47 and my personal rules for self-employment in episode 11, I wanted today to be more about the big picture.
How my business has evolved
If you look at my business today versus five years ago, it looks completely different.
I’ve launched and shut down income streams, including a Patreon.
I also spent a significant amount of time doubling down on creator tips, but after the Made on YouTube era, I decided to pull back.
I’ve since returned to my roots as a fashion, beauty, and lifestyle creator.
The strategy now is all about ROI and control. I focus on platforms where I see a direct return and where I own the connection to my audience. However, the marketing funnel remains essential:
Top of funnel: Short-form content for discovery.
Middle of funnel: Long-form content to build deep trust.
Bottom of funnel: Great offers to create repeat customers.
Despite the growth, I still keep my team lean. It’s mostly just me, with help from an accountant during tax season, a lawyer, a virtual assistant, an SEO specialist for the website, and occasional contractors like photographers and virtual assistants.
The hardest moments you didn’t see
Social media usually only shows the highlight reel, but there have been incredibly difficult seasons.
In 2024, I hit a massive wall where I ran out of ideas for my content creation videos.
I ended up scrapping that entire content pillar to go back to vlogging, which resulted in a loss of income and audience.
Then there is the comparison trap. It’s hard not to notice creators who started long after me blowing past my follower counts.
In those moments, I have to remind myself that I don’t just want an audience—I want an aligned audience.
The financial inconsistency is also a constant hurdle.
When your monthly income can range anywhere from $500 to $10,000 you have to develop a very thick skin and a disciplined approach to money.
The biggest difference-makers
How have I actually stayed in business for five years? It comes down to four main pillars:
Lifestyle: Moving to Hoboken in 2021 was a game-changer. It is significantly cheaper to run a business in New Jersey than NYC, and having a dedicated work-from-home space has improved my productivity and mental health.
Mindset: I stopped thinking about when I would finally arrive. I recently heard Joseph Altuzarra on the Let’s Get Dressed podcast talking about how success is more about alignment than scale, and that resonated deeply.
Support system: My offline support keeps me grounded. Whether it’s Andrew, my parents, my friend Caitlin, or my therapist, they help me emotionally regulate, manage my finances, and live a fulfilling real life outside of the screen.
Self-belief: I’ve learned to stand by my pricing and say no to unaligned offers. I carry the knowledge that every second I spend building this business is an investment in myself.
If I were starting today
The landscape has changed, and if I were starting from scratch in 2026, I would simplify my focus.
You need one long-form platform and one short-form platform to find balance. Think:
YouTube and Instagram
A Podcast and TikTok
A Blog and Pinterest
I would also immediately establish one active income stream (like brand deals or consulting) alongside one passive income stream (like affiliates or digital products).
Milestones and memories from the last 5 years
Looking back at the timeline, I’m proud of how far this has come:
2021: My first full year in business and the era of Clubhouse rooms
2022: Celebrated the 10-year anniversary of my blog and hit 10K subscribers on YouTube
2023: Spoke at my first virtual creator conference and launched my digital course
2024: Made my first national TV appearance, went on my first overnight brand trip, and officially trademarked my blog and podcast
2025: Qualified for Mediavine, was featured on the YouTube official blog, and did a full rebrand shoot
Summary
Thank you for being part of this journey for the last five years. Whether you’ve been here since the 2012 blog days or you just found the podcast today, I’m so grateful to have you in this community!
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