Going From 9-5 to Freelancer on the Road
I’ve been asked by our crew on @wilddrivelife to share some freelance business tips and more about how I got started in 2018! I wanted to share my experience of leaving my full-time job to start Wild Roots and working for myself. How did I work up from part-time to a full schedule of client projects?
Let’s dive in with some honest freelance design business tips, Q&A, and a few follow up links to help you in navigating your next steps toward freelancing.
Big Picture Thoughts on Freelancing:
Are you looking for a way to finance a full-time or semi-nomadic lifestyle? Do you have a stubborn desire to be your own boss? Are you looking for a bonus side hustle to supplement your full-time job and add more to your savings while you work toward other goals?
Freelancing accomplished all of these things for me, personally, at different times over the last four years. It’s a venture that evolves every day. With that in mind, don’t be scared if what you want to focus on shifts or narrows over time. I’m still working on that now, four years into working for myself full-time.
Whether you aim to write, design, consult, coach or do something creative in-between — there are dozens of options to explore when it comes to freelancing, remote work, and generating a mobile income online in general terms. You could even argue there are TOO many options! I certainly feel that way sometimes.
What is a freelancer?
A freelancer is a term commonly used for a person who is self-employed and is not necessarily committed to a particular employer long-term. You have to manage your own finances, estimated tax payments, health insurance and retirement plan. You set your own hours and prices. How much you make largely depends on your own motivation and discipline. That’s an important consideration.
Freelancing is what you make of it. You could hop on Upwork.com, take a few jobs here and there and leave it at that. Another option is to really dive in, market yourself and create your own full-time venture.
It took me a little over two years to establish enough discipline and a base of trust with clients to be working full-time at Wild Roots. Full time to me = 30 hrs./week on average.
Roadblocks to Branching Out on Your Own
The major roadblock for me to dip my toes into work OUTSIDE of the traditional W-2 was basic fear of the unknown, fear of failure and the BIG question of where to begin. I’m also a very social person. I derive a lot of joy from communication and collaboration. I’m a self-starter, but am I THAT motivated?
I asked myself a lot more questions… Can I even make this work?! How do I charge what I’m worth and exceed expectations? Where do I find clients that will trust me when I’m first starting out?!
Starting your own freelance business can be both intimidating and overwhelming. I feel your pain!
I hope that my non-traditional, follow your gut, DIY to freelance story helps in some small way as you navigate YOUR personal journey.
We all start from a different place and have different skills, but we can all learn from each other’s experiences. Take bits and pieces, shape them to fit your situation and goals and GO FOR IT. Otherwise you’ll always wonder, “What if?”.
Go for it then write me an email about how you went for it!
What About Remote Jobs?
Remote-work is typically more of a traditional W-2 employee situation for a specific company. You get to work your job from home or from the road, or wherever you choose. We’ve met a lot of tiny home dwellers and people living a mobile lifestyle who work remotely for a company. They still have benefits, vacation time, etc. they just get to work from anywhere. Honestly, this situation is pretty excellent, if you ask me! Especially if you like what you do! Indeed and Linkedin both have filters for remote work now. Start browsing!
What fields translate well to remote work / freelancing?
MOST jobs/tasks involving a computer can be done remotely.
The bulk of my freelance work is in marketing and branding. This includes web and graphic design, print media design, copywriting, consulting and strategy, social media, etc. but so many diverse fields can be applied to a remote working or freelance business situation.
Freelancer Personal Branding, Quick Tips:
- Be versatile. Never stop learning.
- Sharpen your intuition.
- Anticipate needs.
- Be essential.
- BE YOURSELF.
Why should someone choose to work with you over the thousands of other freelancers in my field, many times offering a lower rate for the same services? What makes YOUR brand special?
I want people I work with to know that THEY MATTER TO ME because they do. This applies to our approach to this blog and our social media platforms too.
Whether you’re in marketing, hospitality, retail or anything dealing with people, really, you’re in the people business. You should first and foremost hone in your skills of COMMUNICATION, empathy, and intuition.
Question and Answer Section
WHAT DO YOU DO FOR REMOTE WORK?
Wild Roots offers small business owners and nonprofit leaders a range of personalized brand design and consulting services. I focus on organizations in recreation and tourism, since that’s where my experience and passion is too. I love helping clients with:
- Web Design
- Marketing/Branding Strategy (digital marketing plans, rebranding campaigns, etc.)
- Print & Digital Design (magazines/layouts, logos, advertising, print media)
- I sub out photography services because I don’t have time to be a pro at that. Plus it gives me a change to support fellow friends who freelance!
I am not a coder. I prefer to leave that to the experts because I don’t enjoy that type of work, to be honest. There are dozens of options to create a customized website for clients without diving too deep into the code. Knowledge of the basics and the ability to problem solve/research has been more than sufficient to date. Some clients want to be able to easily manage and edit their own website. Others are like, “Nope… just make it beautiful and functional, I don’t want to touch it.”
The other services I offer are unique to the client, their starting point and their goals.
DO YOU HAVE A DEGREE IN MARKETING OR SOCIAL MEDIA OR WERE YOU ABLE TO JUST GET STARTED IN IT ORGANICALLY?
I have a B.S. in Business Administration with a concentration in Accounting. Not exactly marketing but the foundation of detail oriented, analytical thinking has been a huge help in my career so far.
The love for and skills in marketing came from work experience. There was an opportunity to take on that role within the 350-site southern Maine camping resort I managed and I dove in with a smile.
I taught myself the Adobe Suite (InDesign, Photoshop, Illustrator) over the course of a few years on the job, very gradually. I wasn’t great at first, learning the programs was frustrating but I LOVED it. That’s the key, you have to enjoy it to keep working at it, especially if it’s challenging.
I observed others, A LOT. I read articles, kept up with statistics and trends in marketing and applied pieces of everything to my personal approach and exploration of branding.
Through that journey I was able to grow the campground’s social media following by 300% over two years. I leveraged email marketing and social media branding to raise us from #8 to #1 on Trip Advisor, gaining hundreds of authentic reviews to strengthen our brand loyalty.
KEY ATTRIBUTES AS A FREELANCER:
ANY TIPS ON GETTING STARTED AS A FREELANCER?
- Learn on the job, if you can. What skills can you gather before going out on your own?
- Explore free education opportunities.
- Build a network (even if it’s really small at first).
- MAKE THAT FIRST PITCH!
- Choose the right clients (there may be some trial & error here…)
It’s hard to gauge the viability of your self employment dreams before you test things out and give yourself a dang chance.
I learned on the job and tested my marketing skills out for three years before feeling confident enough to pitch my first web design proposal to a tourism related non-profit. I watched A LOT of YouTube videos and read through countless blogs and articles. What more can you learn NOW?
That first project felt like the right fit and right timing. Even then I was like, “CAN I DO THIS?!” If you’re thinking that, trust me… you’re not alone. It’s scary. But what’s the worst that could happen, honestly?
A year prior to that first pitch, I was invited to join the marketing committee at that same non-profit. It helped build the face-to-face relationship and I think, earn me a YES on that first pitch. Having a network to build from is really nice. You can always start with your friends and family
Forging that connection helped spread the word about my energy and personalized approach to helping small businesses and non-profits with their marketing. Word of mouth is SO CRUCIAL. They’re still a major client of mine today and I get a lot of referrals from them.
You HAVE to be willing to try and *gasp* be told, “No, thanks.”. If you’re YOU and you believe in what you offer than you WILL get a yes. Sometimes it’s not so much about getting any client to pick you but YOU seeking out the right clients. Use your gut and do some digging.
WHAT WERE YOUR INITIAL GOALS WITH FREELANCING?
My initial goals were to expand my skills in marketing and prove to myself that I could earn income outside of a W-2. Any income! It was so scary.
When I secured my first website design project, we were still paying off our student loan debt. We didn’t have the bus or the plans to do what we’re currently doing. I knew the best (least risky) choice was to keep a full-time gig until our financial equation improved. Bonus if I’m able to make this side hustle work and help us reach out debt-free goal even sooner.
At the time freelancing was simply an effort to manifest my inner desire for new challenges/growth; to test things out. I had been with the campground for almost four years, I was itching to expand my experience.
Don’t be afraid if your goals/vision evolves over time. The important thing is that you’re giving yourself a chance.
HOW DO YOU BEST PREPARE TO FREELANCE IN A FIELD?
- Evaluate the market/potential clients/competitors.
- Evaluate your current skills and toolkit. What do you need to do the work and do it well?
- Develop YOUR brand. What makes YOU a better choice than the web designer across town or someone offering 1/2 the rate on E-lance?
- LEARN as much as humanly possible about your field.
You’ll probably still feel underprepared at times but learning is half the fun. Build a foundation of tools, favorite blogs, apps, websites, etc. for information and tips on your field. Google “Best (insert your field of interest here) newsletters to subscribe to”. For example, “Best content marketing newsletters to subscribe to”
ANY APP SUGGESTIONS FOR TIMEKEEPING, INVOICING, ETC.?
Get an app and routine down for timekeeping and accounting. You don’t want to have to stress about these things.
I use Toggl for tracking projects and billable hours. About half of my work is project based, half is hourly. This mix will be all up to you, my friends!
I use Wave to create invoices, take payments (fees are comparable to PayPal and the like) and track business expenses for tax time. Wave is free to use minus the credit card processing fees when clients pay you online. I also love their reports (receivables, income statements, etc.).
I’ll add a full list of resources at the end of this blog post.
HOW DO YOU FIND CLIENTS?
Most of my clients come from word of mouth or very casual networking.
By networking I simply mean I meet people in our travels or via social media, we chat and somehow what I do for work comes up and sometimes leads to a job.
Networking events are a GREAT option, too.
My first freelance client was a Chamber of Commerce which is a non-profit made up of a large network of small businesses. This was GREAT because I got a lot of word of mouth referrals as a result and still do.
I can’t speak personally for online freelance job board resources like 99Designs or Fiverr, but I’ll post a few sites like this at the end of this post in the resources section.
You have to start somewhere. My suggestion is to begin with your personal network and branch out as you go.
HOW DO YOU DECIDE WHAT TO CHARGE FOR AN HOURLY/PROJECT RATE?
First I researched the hourly rate and project rate ranges in my field online. Typically you can get a feel for what you should charge based on the range and where you fall in terms of experience/skill. I charge more now than I did in 2016. As you build your portfolio and credibility, you can increase your rates.
I also ask myself HOW difficult/simple the project will be, estimate the number of hours it’ll take and go from there.
Another thing you could start with is what you’re currently getting paid at your job (are you happy or unhappy with that figure?). There are also other benefits beyond your rate/salary that sometimes we forget about factoring in. Your employer pays half of your FICA taxes (social security and medicare), potentially your healthcare, vacation time, etc. — You are (hopefully) withholding income taxes automatically each pay period as well. All of that valuable stuff will be up to you if you’re out on your own.
This is why a side hustle or remote work for a specific company is are attractive options for flexibility and stability. Maybe these options are a better match to start with or pursue long term. It’s all about what feels right for YOU and what works with your lifestyle and goals.
For now, freelancing is a simple and comfortable option for me as we explore this short-term nomadic leap of ours. This may change in the future and that’s okay! ?
I’m just mentioning all this to give you different angles to mull over.
IS IT HARD TO FIND WI-FI? IS A MOBILE HOTSPOT SUFFICIENT ON THE ROAD?
It’s can be difficult to find Wi-Fi but it all depends on your travels and what type of work you’re doing. There are free and low-cost Wi-Fi options at truck stops, cafés, etc. if you’re near major highways and towns.
If our goal is to boondock for two weeks in the Arizona desert, I’m probably not going to get as much work done because a lot of what I do requires a strong internet connection. If we’re planning to stay with family or friends for a while — SCORE, let’s get to work. We plan ahead for these things.
I’ve used my personal hotspot with success during our travels, but it does get hung up and frustrating with functions beyond the basic email/web search.
CELLULAR SIGNAL BOOSTER REVIEW (updated February 2019)
We recently upgraded our mobile internet connectivity setup with a cell signal booster from WeBoost — what a difference! It enhances our signal strength even in more remote locations. We have their Drive 4GX-RV cellular signal booster.
When you’re in remote locations, there are only so many cell phone towers and everyone is trying to feed off the same signal. It’s not perfect but having our cell booster makes a big difference.
FMI on WeBoost cell signal boosters, read our full product review blog here.
HOW DID YOU FIND THE TIME AND ENERGY TO SIDE HUSTLE WHILE WORKING A FULL-TIME JOB? (BEFORE BUS LIFE!)
Choose one skill or one client to start a relationship with and build from there. Don’t overwhelm yourself right off the bat thinking that you should have a full roster of clients and six figures of income right away. Things take time. Things take effort.
I started with ONE website for a client and gave it my all in my free time outside of my very demanding full-time job at the time.
That job/client led to other work through word of mouth and about 8 months later I left my 50+ hour/week job for another position in marketing that was only 32 hours a week.
This transition and additional free time allowed for me to dip a few more toes into the freelance game. 12 months after that I was full-time on my own traveling this beautiful country of ours in a bus with my BOYS. Ben and Moose, of course.
Be patient with yourself. If you have that voice inside and real desire to work for yourself then work through a one to five year plan to get there. You’re worth it.
STAYING ORGANIZED — HOW DO YOU SWITCH YOUR BRAIN BETWEEN DIFFERENT PROJECTS? ANY SCHEDULING TOOLS OR APPS TO SUGGEST?
I honestly still struggle with this a bit and I think the experience will be unique to you and your situation.
The first step is getting to know how long certain projects/jobs take you. That’s where the timekeeping apps come in handy. Once you have an idea you can start to categorize your project load based on priority (deadlines) and time.
I’m a fan of knocking out quick projects that come my way early in the morning when my mind is swimming with the day ahead. That way, I don’t let things slip for weeks because they’re “easy”. I can focus on larger projects for the bulk of my work day.
MAKE LISTS. I’m a fan of simple, personally. I keep a list in notes on iCloud (available on all my devices!) And keep track of quick progress notes, deadlines etc. in there. It’s quick and easy.
There are a ton of project management apps out there to track your clients and the various projects you have going on for them too, if that’s more your thing. I’ll post a full list of resources at the end of this post.
Segment your day if you can, it helps. Just because you’re not going to an office doesn’t mean you shouldn’t have a schedule and time limits on certain tasks.
Know when to shut it off, too. Set boundaries with email and text responses. Take days off. Plan around the weather! ?
IS FREELANCING ENOUGH TO COVER YOUR LIVING EXPENSES IN THE BUS?
Yes. I was REALLY scared at first that it wouldn’t be. I’m such a type-a budget conscious penny pincher at heart. A risk like leaving our jobs and traveling the country did not come naturally to me.
Thankfully Ben has faith and vision enough for the both of us! We also prepared financially by paying off ALL of our debt, finishing the bus with CASH and saving up a nestegg before departure.
Trust me, you don’t want to live tiny AND stress about money. That’s just no fun.
We started living this way in January 2018 after leaving our full-time jobs a month prior. Cut to now and we’re able to sustain everything and save via freelancing, Ben’s rockstar blogging and our affiliate revenue. How long will we do this? Well, I don’t know, but it’s a neat way to experience life for now.
We also have some REALLY great online guides and apparel designs we’re working on for you guys too to build & diversify our income and offerings further. Always evolving.
Remember, the hardest part is starting, pushing GO. The best freelance business tip I can offer is to just give yourself a chance. Especially in an online field where there is less risk and minimal start up cost, why not?!
You can ALWAYS try new things, diversify, pivot, fail, try again, etc. — Nothing about designing your income outside of the 9-5 is easy, I won’t lie to you.
It’s hard. It tests you.
But it’s also a lot of fun.
RESOURCES & HOMEWORK:
QUESTIONS TO ASK YOURSELF TO HELP HONE IN YOUR SPECIALTY AND TARGET MARKET.
WRITE THESE DOWN & really think about the answers.
Keep them safe and review them in a couple of weeks, a month, three months. How have things changed/evolved?
- Who could benefit most from what you have to offer?
- What type of business/clients would you enjoy working with? Describe them.
- What are the top three functions/tasks you’d like to focus on in your freelance work?
- What are three things you enjoy doing and would do for free? Can any of them be applied to work?
- What are three skills you would LOVE to learn more about?
JOB POSTING NETWORKS TO SCOPE OUT FOR FREELANCE CLIENTS/PROJECTS:
FREE APPS FOR ORGANIZATION, TIMEKEEPING AND INVOICING:
If you enjoyed this post and learned something from it, please consider donating a few bucks to our blog to keep us writing these types of resource rich posts. We’re here to help YOU.
FOLLOW UP FOR INSPIRATION. GET READING & GET CREATING!
I highly recommend these books:
- Four Hour Workweek – Tim Ferris — Great tips on time management and passive income.
- The Freelancer’s Bible: Everything You Need to Know to Have the Career of Your Dreams―On Your Terms
- Yes, Please – Amy Poehler — I just love this book, period.
- The Pathfinder: How to Choose or Change Your Career for a Lifetime of Satisfaction and Success
- Travels with Charley in Search of America – John Steinbeck (BONUS, because it’s awesome…)
Sending LOVE and a high five from the road.