What I've Learned From Five Years Of Freelancing

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Five years.

It’s been five years since I started freelancing.

Five years since I voluntarily decided to give up my bi-monthly paychecks, 401K and paid vacations days.

Five years of hustle, deadlines, failures and even a few emotional breakdowns.

But throughout those five years I also broke ground and grew my freelance business to heights I never imagined.

I’ve worked with clients throughout the U.S., Canada, United Kingdom, Austria and Australia.

I made enough money one year to pay off half of my husband’s student loan debt AND put a down payment on our first home.

I negotiated higher pay for myself when I knew I deserved it.

I built the confidence to turn down new business I knew wouldn’t be worth the investment of my time.

I fostered client relationships so strong that they led to future business when those clients went somewhere else.

I made enough money to help support my little family and put even more of that money into savings.

I did that.

ME.

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Pre-flight, preparing a proposal for an international client after visiting them for introductory meetings in Australia.

With the beginning of a new year, many of you reading this may find yourselves in the quiet chaos that is starting your full-time freelance career.

The silent madness of staring deeply into your computer screen almost as if you’re waiting for it to talk back to you while you obsessively refresh your inbox because you’ve been waiting…

Waiting so patiently for that email from that one potential client to come through for what feels like days now but really, it’s only been an hour.

No one tells you how quiet it is.

But you are ready.

Ready to work and no one seems to care that you’re nowhere near the monthly income goal you’ve set for yourself and that all you need is one gig.

One gig, that’s all you need.

You’d be so great at it, too.

You just need the opportunity.

You just need someone to say yes!

You just need that email.

That one email.

Where is that god-forsaken email??

Take a breath.

Yes, freelancing can be maddening but it can also be great. So great.

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Freelancing has also allowed me the freedom to do pro bono work for organizations I believe in, including Gamers Outreach - a non-profit that places medical-grade video game kiosks in children’s hospitals throughout the country.

I started my freelance journey in January 2014. In order to understand why I started freelancing, I need to share a little background into my career at this time.

In 2012, I started working for a public relations agency while my husband (then fiancé) and I lived in Los Angeles. Unknowingly at the time, we’d be moving to Florida some seven months later.

When I told my manager that I needed to quit because we were moving, she offered me the opportunity to continue working from home in Florida. The possibility to continue working in my current role and at my current salary from the other side of the country never even crossed my mind.

I was a Senior Account Executive at the time and thought only executive level employees would be considered for something like this. I was beyond excited and to show my gratitude, I did everything I could to make my Los Angeles team feel like I never left.

Which means I worked… a lot.

I worked at this capacity from my Florida home for 13 months.

During those months I got promoted, married and was traveling back and forth to California on red eyes every two to three weeks for client meetings and new business pitches. When I was home I was maintaining west coast work hours which provided very little personal time for me and my new husband.

To add to the work stress, it was also during this time that my grandmother was diagnosed with cancer and would be undergoing treatment. My family needed me and to be honest, I was just exhausted.

I loved my job and my team but I also knew change was on the horizon.

I took time to think and evaluate the things I needed to make my life feel more balanced.

I loved the job I was doing, just not the heavy work and travel load of being cross-country from the rest of my team.

I needed to feel like I could step away from my computer and not worry about taking longer than ten minutes to reply to my manager if an email came through.

I needed to be available to help my family when they needed me.

I needed income but was fortunate enough to be covered by my husband’s employer’s benefits.

I needed to go freelance.

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Freelancing has taken me to some incredible places and given me the opportunity to work with clients all over the world. Here I am in Fuscl am See, Austria taking a break from our meetings for a quick photo opp.

So I put together a plan to pitch to my boss at the time because I wanted to continue working with my Los Angeles agency and team; the agency and team that had given me so much already, including the opportunity to work from home in a state where I wouldn’t be granted the chance to work with the level of clients I did with them.

I wanted to continue working together, but I simply needed to scale back. I practiced my messaging with my husband (always have your messaging ready, folks) and then presented the idea of going freelance to my boss. I’d continue to manage my biggest client and contribute to any new business within my specialty field, but if I didn’t have the time or if it wasn’t within my particular wheelhouse, I could say no.

She said yes.

And for another year, I continued to work with my Los Angeles agency, except this year I was an hourly freelancer and I loved it.

Looking back, this is also the time I learned one of my first lessons in self-employment:

Don’t be afraid to ask for what you want.

So many people I talk to are afraid of rejection and it is a very fundamental and unpreventable part of being human. You will undoubtedly be turned down throughout your life and career.

But you never know unless you ask and you’ll be surprised what comes from putting yourself out there every now and then.

I knew that when I asked if I could go freelance, the worse outcome would be that the answer was no.

But I also knew I couldn’t continue to work at the level I had been and that my agency wanted to work with me. If they didn’t, they could have let me quit back in LA or found a way to fire me out of the work-from-home arrangement we made.

Even when rejection happens, there’s always opportunity to be found in the “no.”

Always ask for feedback.

Can you help me understand why this isn’t a possibility?

What can I do to improve upon the factors that led you to this conclusion?

If not this opportunity, I hope you’ll keep me in mind if anything in the future comes about.

Never leave the conversation at “no.”

Ask for more, take that knowledge and put it into everything you do from there.

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It isn’t all fun. This is what happens when there isn’t any wifi on your cross-country flight and you have 100 client emails to send out before the weekend. You order a glass of pinot, some french onion soup and work from the hotel lobby so you’re not tempted to fall asleep… well, almost..

I think this is also a good time for me to point out that I’m one of the few people who started their freelance career with a client.

A client I had history with, who liked working with me and wanted to support me. This isn’t common and I was very fortunate.

I also created this opportunity for myself through hard work, open dialogue and a track record for delivering results.

I hope this part of my story also helps open your eyes to the potential opportunities that are available in your life.

Don’t limit yourself to what people say is status quo.

Don’t be afraid to create your own opportunities.

Like I said, I continued to work as a freelancer with my agency for another year. The work came to an end after the big client I was managing decided to take all of their communications team in house and the manager who had always been my champion, took a job at another agency.

I knew this wouldn’t last forever but after a year of freelancing, I was also presented with my first month of no client work to be had.

I remember waking up and sitting at my desk and thinking to myself, “Shit.”

That’s all.

Just, “Shit.”

Since I transitioned straight into freelancing basically doing what I had been doing for the same company I’d been doing it for, I never announced to my network or social media that I went freelance. I never networked and I had zero leads.

Which brings me to lesson number two:

You should always be networking.

I started by reaching out to people who throughout my career I felt had always supported me, and people who I had always looked up to. I’ve written about this before, but networking within your existing network is the best way for starting your freelance business.

These emails weren’t, “Hi, I need work. Can you hire me?”

They were, “Hi. I’ve started freelancing. Can we connect? I’d love your insight.”

Freelancing is a lone wolf business but that doesn’t mean you can’t create your own pack.

I asked for advice. I shared what I was looking for and what I aim to provide. I asked to be kept in mind if they ever need the kind of help I can lend and to be connected with anyone who may benefit from my services.

It didn’t take long before I had my first lead which led to my first client and since then, I’ve only had one other three-month down period. And it was one I opted to take because throughout my entire life, since I was 15 working at my mom’s real estate office to 31 working as a freelance consultant, I’d never taken more than two weeks off (and even during those two weeks, I was on call).

I worked three jobs throughout college and took summer courses to be able to finish on time because I was a scholarship kid who would graduate in the heart of the worse recession of our lifetime.

And I’ve worked everyday since then to make sure no one has to worry about reaching into their own pockets to care for me.

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While planning our two week trip to Costa Rica, I was able to pick up a side gig doing photography work for a local business in exchange for a discount on our lodging. Freelancing has always empowered me to find ways to maximize all of my skills.

Now, there are dozens - if not, hundreds - of lessons I’ve learned over the last five years and they’re all things I discuss pretty actively throughout this website, like:

Five Things To Include In Every Scope Of Work

When To Turn Down New Business

How To Determine Your Hourly Rate

Etc.

Etc.

Etc.

But for the sake of this article, I think it’s more important to focus on some of the emotional learnings that freelancing has taught me because it hasn’t been an easy path.

But then again, does anyone think it would be?

Freelancing is like a constant state of discomfort. Just when you think you’ve put yourself in a position you can stay in for awhile, that pain in your side comes back forcing you to turn over and try again.

It’s like playing, “The floor is lava” with your mental stability. Take one step out of balance and boom! The floor is lava! Hot, soul-sucking lava.

It can also feel like running a marathon, where the road just keeps getting longer and the soles of your feet sink deeper into the concrete with every stride you make.

But just like a marathon there’s a point where something magical happens.

The finish line is in sight and the pain starts to turn into bliss as you get closer and closer to reaching the goal you’ve been training so hard and long for.

You can see it, you’re almost there, you raise your arms to the sky and rejoice as you cross the metaphorical finish line that is seeing a fat, well-earned paycheck clear your bank account.

Now just move 30-40% into your savings account for taxes and then get back to enjoying the moment.

Hooray! Money!

You’ve earned it and there is seriously no better feeling than knowing that YOU DID THAT. You ventured out on your own, you secured this client, you worked your ass off and you earned that paycheck.

Freelance money is so much better than any paycheck you could ever receive as a full-time employee.

Sure, the amount could vary and yes, you really do need to take out 30-40% of your freelance check for taxes but the point is:

Every paycheck you receive as a freelancer is a step in a forward direction.

This milestone isn’t only validating but it gives you the ability to keep freelancing, to search for new clients and continue to push yourself in the direction you want to go in.

That’s the beauty of it all.

Freelancing, when done right, should empower you to do the things you’ve always wanted to do.

Live in Barcelona for a month and work on client projects from the coffee shop down the street.

Hustle while your kids are at school so you can be truly present for all of their soccer games.

Limit your office hours to four days a week so you can find greater mental balance.

Turn your passion into your profession and do if from the comfort of your pajamas if that’s what makes you happy.

No matter why you decided to start freelancing, it’s a decision you made. Not because it’d be easy. But because it’d be a challenge worth the challenge.

Own it.

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While I will admit that one of freelancing’s downfalls is that I can become quite the hermit to my home office, I love that I can literally work from anywhere that has an internet connection. When the weather’s nice, I like to get out to a local spot for lunch or use the opportunity to sync up with another freelancer friend and collaborate.

Now, this article has gotten pretty long and turned into more of a stream of consciousness (Welcome to my mind!) so let me start to wrap things up by giving you a cliff notes version of some valuable lessons I’ve picked up along the way these last five years.

Dream clients are just that - dreams.

Don’t get caught up in perfection. Get caught up in what gets you paid.

You actually have to submit an invoice to get paid. (If you’re laughing, you’d be surprised how many new freelancers I’ve had to explain this to.)

Not everyone will like working with you. That doesn’t mean you’re not good at what you do.

Always take out 30-40% of your paychecks for taxes the day that money hits your bank. Do not wait. Do not pass go. Do not collect $200.

You will get fired.

You will have to fire clients.

You will have to chase paychecks. Not all the time. Hopefully not often. But at one point or another, it will happen.

You are allowed to take days off.

Take days off.

Over communicate.

Be upfront with clients when they want work outside of the scope of work. Do not let it slide, not even once.

Set office hours and keep them.

Be selective.

Be confident in your value and don’t let any potential client try to convince you otherwise.

Don’t work with those types of clients.

Take on work that challenges you.

Show off your work.

High-five people who do good work.

Help other people find work.

Be proud of what you do.

Freelancing is something to be proud of.

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During my first year of freelancing, my previous manager hired me to live and work from San Francisco for two weeks over the summer. It allowed me to get a taste of what “nomad” life is like. I had a murphy bed, walked the two miles to the office everyday and got to experience what life in the Bay is actually like.

While I’ve gotten my fair share of head tilts when I explain to people what I do, especially at family gatherings, I typically wrap up the dialogue with, “I get paid a premium to create communications strategies for companies who don’t know how to do it themselves.”

Then it’s like a light bulb goes of.

Did she say she gets paid?

Yes, I get paid.

Freelance ain’t free, Uncle Ernest.

Now, I’ve been rambling for awhile (two days of writing for context) and if you’ve made it this far, I truly hope you’ve learned something about what this freelance life can provide.

These five years have been a little all over the place for me but they’ve also been the most rewarding five years of my entire career.

I learned more about business and leadership during my first year of freelancing than I ever would have if I kept climbing up the corporate ladder.

I think there’s also this mistaken assumption from some nine-to-fivers that I must be freelancing because I can’t get a “real job” but the truth is, I get approached by recruiters and turn down full-time opportunities pretty often.

If I ever go back to working in a corporate environment it’s going to be because it’s a job I believe in and think worth giving up the lifestyle I’ve created for myself and my family.

There are very few opportunities that would be worth it to me.

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This is me now, five years in and I’m still happy, still proud, still wouldn’t have it any other way. I’m scaling back my freelance workload in 2019 to focus on building The Scope and connecting with more freelancers in our growing community.

These five years are also what led me to creating The Scope in hopes it’s a small haven for people to find answers to the questions about freelancing they’re looking for.

I know freelancing isn’t easy and it might even be a little scary, but you’ve got support here (and here and here - shameless, I know.) and I hope some of the resources you find throughout the site make it feel a little more doable and maybe even… exciting.

Because you can do it.

I’m rooting for you.

You’ve got this.


AUDREY ADAIR IS THE FOUNDER OF ‘THE SCOPE’ AND A SEASONED FREELANCE COMMUNICATIONS PROFESSIONAL. SHE STARTED ‘THE SCOPE’ TO PROVIDE RESOURCES AND COMMUNITY TO FREELANCERS AND THE SELF-EMPLOYED. CONNECT WITH AUDREY ON INSTAGRAM, YOUTUBE AND LINKEDIN.