Freelancer Success Stories – Kevin Udy

Freelancer Success Stories

Welcome to my interview series, Freelancer Success Stories! Set in a Q&A format, the interviews are designed to place the spotlight on people just like you and me, who have made the leap into freelance work, either on a full-time basis, or as a side hustle. Find out how they did it, what they love about freelancing, and what they hate. Discover their best tips, as well as their favorite tools. My guest this week is Kevin Udy, a freelance digital marketing consultant and traveller who lives and works on the road full-time. Ready? Let’s dive in!

Name: Kevin Udy

Location: Home base is Fort Collins, CO (currently slow traveling away from home)


I am in my late 30s & I hail from Colorado. I am currently slow-traveling and living in an RV with my partner Carrie and our dog Phoenix. I enjoy cultivating a well-balanced life and dabble in a variety of hobbies. I am intentionally frugal and saving toward financial independence while prioritizing flexibility and freedom.

How long have you been doing freelance work? 

More than 5 years.

Tell us about your freelance business, in 100 words or less.

I’m a solo consultant, helping businesses with technical digital marketing. I help improve the web presence and reach of businesses that want to find customers on the internet.

What do you consider to be your specialty? How does it help you in your business?

My ideal client is a marketing company who needs specialized help with the more technical aspects of digital marketing for their clients.

What made you become a freelancer?

I received enough referrals from friends, family, and work connections that it was a natural fit to start taking on freelance work while still employed at my full-time job. At the time it helped me save more money toward my financial goals, faster.

What do you love most about freelance work, and why?

The flexibility to do work when it best fits into my days and weeks. Flexibility is key for me to enjoy our current travels and enjoy life.

What do you hate about it?

I am not a natural at sales/business development, but it’s a work in progress! Loneliness can also be an issue.

Tell us about your first paid job. How did you land your first client?

It was a long time ago, so not really! I am certain it was a referral from a friend/family member, and it was easy to land because the client had immediate trust in my ability to execute the job.

Do you think aspiring freelancers should take unpaid work to gain experience? Why or why not?

I believe the best path if you don’t quite have the skills or confidence to market yourself as a paid freelancer is to work on your own projects to gain experience, or find a job that will pay you to learn the skills you need to go out on your own.

Do you feel you’re charging what you’re worth?

I believe I am slightly under-charging what I am worth right now – in the past year I transitioned from mostly full-time work at a traditional job to working solely as a freelancer; I started out with a lower rate to make sure that I wasn’t priced too high while I build a customer base.

How do you typically find new clients?

My process isn’t easily replicable, but it has worked wonderfully. I spent 10 years working in the digital marketing industry, and networking with my peers, before relying on freelance work. As soon as I left my full-time job and started freelancing more, those connections came through. I haven’t really advertised my services at all, but I still get plenty of leads from referrals and industry contacts that would like to work with me.

Have you ever had to fire a client?

No – but there have been a number that I probably should have fired. Evaluating and only working with clients who are a good fit is a skill that I really need to work on!

Name 3 tools (apps, equipment) that you can’t live without. What makes them so great?

The Google suite of tools (Gmail, Drive, etc.), WordPress (software), and my Verizon “jetpack” for mobile internet.

What is your #1 productivity hack?

Sit down and tackle a big or annoying task first thing in the morning, get it over with, and the rest of the day will be smoother without that task hanging over your head.

Do you outsource tasks? Why or why not? If so, which ones?

No, I don’t. I generally enjoy understanding and gaining proficiency in all aspects of entrepreneurship – so I don’t mind doing my own bookkeeping and taxes, etc. I also aim to not be so busy with work tasks that I can’t do everything myself.

In your opinion, what is the most important skill required for freelance work, and why?

Organization. Without the ability to organize projects, tasks, emails, etc. freelancing quickly becomes overwhelming.

Do you consider yourself a strong time manager? How do you stay organized?

Absolutely. I use a number of digital tools to keep my pending tasks organized, and I use a time tracking app to help me invoice clients for billable work and measure my accuracy with estimating projects.

How do you balance freelancing with your 9-5?

Until May 2018, I did work a full-time job while also freelancing. For the past year I’ve worked solely as a freelancer. When I worked my job I made it clear to freelance clients that their work was a secondary priority for me, and that I would only focus on freelance work 2 or 3 times per week (usually Wednesday evenings and Saturday/Sunday).

Where do you do most of your work?

My “home office” in my RV. I love being able to utilize 2 large computer screens, and avoiding distractions.

Do you use a co-working space? Tell us a bit about it.

When I am home (or within range of a space), I spend 1 or 2 days per week in a coworking space. Because I don’t have a permanent desk, these days I work from my laptop (with only 1 screen!). Part of the reason I am a member at coworking spaces is to connect with other people, so I try to sit in the “common” area and chat throughout the day with other members.

Name an entrepreneur/freelancer/influencer who inspires you. What is it about their story/message that resonates?

The hosts of the podcast, “Scavenger Life” are inspirational to me because they run a successful eBay sales business while maintaining flexibility and freedom, while not overwhelming their lives without too much work. They are passionate about their work, and they self-evaluate and evolve over time. I also love how *real* they are with their audience.

If you starting over today, what would you do differently?

I can’t think of any big changes I’d want to make if I had the chance to start over! Possibly leaving my job 1 year earlier?

What is the one piece of advice you would give to someone wanting to start a freelance side hustle?

Have a rock-solid understanding of your monthly expenses, and how much you need to make to cover yourself financially. Relatedly, be realistic about your projections, and understand that building a business takes time, and work is never “guaranteed” (don’t put all your eggs in one basket!).

MMMThank you Kevin for sharing some of your freelance journey with us! I really appreciate how you’ve prioritized flexibility within your work schedule, and how staying organized has played an important role in maintaining that balance. I also love your productivity hack!

Make sure you check in next Friday, as I interview Sandra Parsons, a Canadian freelance writer specializing in personal finance, travel, and psychology.

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