Freelancer Spotlight: Madison Hanna, Brand Strategist & Copywriter

Freelancer Spotlight: Madison Hanna, Brand Strategist & Copywriter

We interviewed Madison Hanna an accomplished brand strategist & copywriter. In this profile she shares her path to freelancing, her best tips for other freelancers and her outlook on the future of freelance

Ron Toledo

Mar 14



The Kalo Freelancer Profile series highlights the best and brightest in the independent workforce. 


Name: Madison Hanna
Location:  Denver, Colorado
Skills:  Storytelling, Copywriting, Photography, Media Relations
Find me: LinkedIn [bite-sized branding & copywriting guidance ], Instagram [brand spotlights & tips/tricks to up your copywriting game]
Everything else: Curated Compass [brand therapy for the modern business]

About Madison

How long have you been freelancing?
I started freelancing in January 2017.

Why did you become a freelancer?
It all started because I wanted an “adult gap year.” I was working in San Francisco at a high-intensity PR agency and was ready to hit a life reset. My goal was to eliminate life clutter and simplify. I saved a boatload of cash and bought a one-way ticket to Thailand. It was through my travels in 2017, I was introduced to the world of location-independence and freelancing. Once I secured my first client, I was hooked.

How has going from full-time to freelance changed your outlook on your career?
My freelance career stands on the foundation of my full-time 9-5 experience. It was through well-seasoned managers, big-box accounts, and an inspiring work environment I built my freelance career. I’ve cultivated the confidence and skills of a corporate environment, but now have the freedom to propel my career forward on my own terms. Through freelancing, I’ve become a bold yet humble professional. Anything feels possible!

What's been your biggest shock adjusting to freelancing?
In my corporate cocoon, I was entitled to a bi-weekly check - there was never a question in my mind whether or not it would come. Since freelancing, the question weighs on my mind annoyingly often. I’m always looking ahead and planning for the unexpected. Sometimes clients run out of budget or they drop you because of unforeseen circumstances. It’s up to me to get creative and hustle so I can maintain my financial stability.

How has being a freelancer changed your life?
My relationships and life experiences are so much richer. I choose my own schedule and environment - which allows me to vividly and tangibly do things I’d never be able to do while wearing golden handcuffs in a 9-5 position.
What's the best thing about freelancing?
The ability to problem-solve, grow, and work on a mishmash of projects. You get a true brain and creativity workout every day. The challenge for anyone freelancing is how to keep your work, sanity, and health afloat. It’s a wonderful challenge for those willing to take risks and who value growth.

What's the worst thing about freelancing?
When you start freelancing you will inevitably say “yes” to opportunities that don’t necessarily match your value. This traps you in a situation where you feel “grateful” to the client for just hiring you. It can become a dangerous and precarious relationship. In small ways, they might take advantage of your skills and time. One client took it too far and ended up asking me to work in advance of payment. Because I was new to the scene and took him for his word, well - you can imagine what happened. He never paid me. It sucks to be felt taken advantage of.


Workflows and Habits

What does your typical workday look like?
My mornings are sacred. I try to meditate to set a balanced and level-headed vibe for the day. I engage on Linkedin and Instagram with prospective clients and industry peers. Then I review my to-do list from the evening before. My list consists of a mix of client deliverables and new business outreach. I’ve designed my schedule so I work about 5-6 hours of work a day. Some days do I go over? For sure. Some days am I under? Absolutely. It’s all about a holistic balance.

What is the first action you take when you start your workday?
Meditation. I highly recommend Headspace. You’ll think you don’t have ten minutes to devote to it, but let me tell you - you have ten minutes. It’s a great tool to help you head into the workday feeling relaxed and level-headed. These emotional benefits will positively impact your day in noticeable ways.

What do you have any quirky workflows or habits?
Not so much quirky, but I do bake in a good 45 minute walk into my day to break it up into chunks. After being outside, it’s like I’ve had two cups of mental coffee. I’m ready to dive into a more arduous project like long-form writing.

What's your workplace setup look like?
I swear I work twice as fast with my bluetooth wireless mouse. I’ve had it for a year and it’s starting to punk out on me. If anyone has a recommendation for a new one, I’m all ears!.

What's your favorite place to freelance from?
So many wonderful environments fuel my productivity. Right now I enjoy brightly lit environments with bottomless libations and a hiking trail within walking distance. I enjoy small town vibes. I’ve been working from Colorado Springs recently - it’s a quirky town with lots of character. It is nestled at the base of the Rocky Mountains.

What’s an app or tool in your toolkit that makes your work life easier? [besides Kalo].
I’m a big fan of  It’s a video chatting service I use to connect with clients, network, and brainstorm with my team. Great UX and you can brand the “room” with your company name and people “knock” to get in. I use the free version - it allows up to four participants.


Freelancing Lessons Learned

What’s your favorite project you've worked on?
Right now I’m helping my cousin and her husband build a local brewpub called Mechanistic Brewing in western Pennsylvania. They lean on me for branding, copy, and marketing guidance. I offer input on everything from beer names, merchandise, to interior design decisions. To holistically advise on their branding strategy from the early origins of their business, is really special.

What’s your biggest challenge freelancing?
New client acquisition. It takes a lot of effort, time, and resources to build relationships with prospective clients. You want to do the heavy legwork to ensure it’s a positive, fruitful, and long-term match. This means a lot of stalking, meetings, and research - all while juggling active client projects.

Best piece of advice you’ve been given that helped your freelance career?
Action cures fear (thanks to Julie from Creative Blazer for that one). Some days you’re overwhelmed and paralyzed with unrest and anxiety. You don’t know where to start. Just the act of doing of something - clearing out your inbox, catching up on newsletters, updating your email signature - can propel your activity forward. Just do something, the rest will follow

What's your best advice for other freelancers just starting out?
Start your hustle while working a full-time gig. This will be your first crash course in freelancing. Get those testimonials, baseline rates, and feel for what your life will be like before you make the jump. You’ll remove some pressure and have sewn in confidence to build a business that reflects your worth.

What advice do you have for freelancers who are struggling with keeping on top of their workload
Find tools that play to your needs. If you struggle with accounting, use QuickBooks Self-Employed to track client expenses and revenue. If organization is your issue, dive head first into G Suite.

How do you find balance and keep your freelance career separate from your regular life
When I make my (realistic) to-do list the night before, I commit to finishing the activities. Once I’m finished, the rest of the day is mine! When you commit to self-managed activities, there’s no reason to feel guilty or overwhelmed. I know there’s always more I can do, but if I let anxiousness overwhelm me, freelancing won’t be sustainable and I’ll burnout before I know it.


The Future of Freelancing

What's a common misconception about freelancing?
A common misconception is that freelancers have the same securities as full-time salaried workers. Freelancers have even more hoops to jump through and challenges to navigate. Everything from healthcare to taxes to steady paychecks to workspaces to workplace community and resources - freelancers have to create and manage it all on their own. While your freelancer friend might be taking a spin class at 11am on a Tuesday, she was up the night before working on a last minute ask from a client until midnight. There’s not a one shoe fits all freelance experience.

What's one thing about being part of the independent workforce you wish you could change?
I wish there was an easier way to find reputable clients. Tools like Kalo support freelancers because they do the client vetting process. It’s great! We need more businesses partnering with software platforms so both parties can benefit. 

What would you like to tell companies that work with freelancers?
Our time is just as valuable. We’re also looking for more efficient, streamlined, and fruitful partnerships that last. It makes our lives easier and our work is higher-quality as a result. We all need to do a better job at seeing each other as people. I think transactional platforms that remove a humanitarian element and enforce transactional practices harms the freelancer community and also gives employers a bad tasting experience as well.

What's your outlook on the future of work and freelancing?
Friends and family consistently reach out to me for advice on how to pursue a freelance career. Employers are now looking for highly talented and hyper-focused freelancers. Tools, processes, job descriptions, and technology are evolving to accommodate the modern workforce. By 2020, more than 40% of the American workforce will be self-employed according to estimates. The freelancing community is only growing - it’s awesome!