How to Go From a Freelancer to a Founder Mindset

A dream life starts with changing your mindset — plus my favorite newsletters and creators to follow

Author

Taylor Cromwell
November 20, 2023

As I mentioned in last week’s newsletter, by far the most important lesson I’ve learned in the year of a half freelancing is how to think like a business owner.

This time last year (just a few months into freelancing) I felt like I was desperately getting by, just scraping for crumbs. I had one client paying me for 10 hours a week and a few other hodgepodge freelance assignments. After years of working on a New York salary, I couldn’t fathom how people handled this lifestyle. I couldn’t envision a life where I was making enough to live in a big city, handle rents, and most importantly have a regular source of income to live a normal life.

It took many months and a lot of blood, sweat, and tears but I eventually got past that low point. Fast forward to this summer, I had some of my first five-figure months and a consistent, yet sustainable, stream of work coming in.

It may sound cliche, but it’s true: changing your mindset will open up so many doors. Over the past year, here’s a few things I’ve focused on while growing a business:

  • ✔️ Increasing my rate with every new client (and not accepting work that’s under my rate)

  • ✔️ Narrowing down the scope of work I offer and how I work with clients

  • ✔️ Drawing firm boundaries on my communication and expectations with clients

  • ✔️ Putting money aside to invest back into the business and back into my personal development (software, courses, etc.)

  • ✔️ Thinking about work through an abundance mindset lens — not through a scarcity mindset

Additionally, this article from Sarah Turner offers some helpful tips for cultivating a business owner mindset. Happy reading!

Ready to dive in? Here are some resources that have really helped me think about entrepreneurship and business:

  1. Freelance to Founder podcast 🎙️ This podcast show helps real-life freelancers grow their businesses and escape the feast-famine lifestyle. I’ve learned an immense amount on all things freelancing from this podcast, including how to set rates (and earn more money), how to define my messaging, communicating value to clients — and so much more.

    P.S. I’m on this episode if you want to listen :)

  2. Ali Abdaal 🎥 is a YouTuber, Podcaster, entrepreneur, and creator that specializes in productivity. He has such an excellent way of teaching topics in a relatable, engaging way. I recommend signing up for his newsletter Sunday Snippets and going on a deep dive into his Youtube channel.

  3. Justin Welsh ✍🏻 is an online creator that teaches creators how to identify, develop, and monetize skills they already have through solopreneurship. If you explore his website you’ll find helpful guides on personal branding, business planning, social media growth — and so much more. I recommend signing up for his newsletter The Saturday Solopreneur. 

  4. Growth in Reverse newsletter 📧 This is by far one of my favorite newsletter subscriptions — and it reminds me each week what is truly possible when you run your own business. Chenell does weekly deep dives on newsletter creators to find out how they grew from 0 to 50k+ subscribers. It includes nitty gritty revenue information and you can find inspiration from people who have built 6 to 7-figure newsletter businesses.

  5. Starter Story 📚 I enjoy introducing people to Starter Story so much so that I should start an affiliate link. Similar to Growth in Reverse, Starter Story breaks down how business owners have found success — but covers a much wider scope than just newsletters. With 4,000+ case studies, they’ll show you how ordinary people built businesses to millions in revenue - all starting from a simple idea or side project.

Screenshot from the Starter Story website

This week’s office on the road 👩🏼‍💻

I’m writing this week’s newsletter from sunny Tuscany. I’ve been enjoying slower internet speeds, time to read, and most, importantly, having lots and lots of pasta. I’m focusing on the rest, relax, think, read, travel, cook side of the success equation.

This week’s Entrepreneur Edit brought you by a lot of pasta and wine

When I have my more stressful working weeks, I have to take a step back and acknowledge how lucky I am to have the flexibility to experience these things. 

Next up: how to conduct the ultimate year in review 🏁

I really enjoy this time of year as things start to slow down. One thing I really love doing in my personal and professional life is to look back at the year and see how I grew, what I learned, and what I’m looking ahead to in the next year.

As a culture, we focus so much on New Year’s resolutions and goals on January 1. I know I’m not alone in forgetting what those even are by mid-march. So in both my professional and personal life, I’ve moved more towards monthly, quarterly, and yearly goals to break down big dreams and goals into bite size pieces. A key component of this is taking time after to reflect, so you can assess how things really matched up your intentions.

Some key questions to ask at the end of the year:

  • What did I achieve?

  • Where did I fall short?

  • What’s something unexpected I learned?

  • What’s something I want to focus in the next chapter? 

I’m going to share more on my thought process on creating and conducting a personal year-end review in next week’s newsletter. Plus, I’m going to share a downloadable template that you can use for your own year-end planning. Stay tuned!

Lastly, my one big goal for the end of the year: help me grow my newsletter list 📈

In order to grow my business and hopefully monetize some new products, I need to boost my email list. I’d love to find more readers that could use this kind of information. Maybe someone in a full-time role that’s looking to monetize a side hobby, someone that’s just starting to freelance or even someone running a full business and wanting to learn more about building sustainably and creating a more full life around work.

Do you know this person? Or better yet, do you know a few people you could share this newsletter with? 

You can also use this link here and share on your social media accounts. I’d be immensely appreciative!

Want to connect or work together? Here are a few ways: