In the early stages of my business, my main goal was to generate enough revenue to provide for myself and my family. Sustainability was my focus, and scaling my business was the furthest thing from my mind.

But in just eight months, I found myself at an unexpected crossroads. I had more work than I could handle on my own and knew I needed to hire help to keep up with demand.

Today, my business has scaled into multiple ventures including a small freelance design agency, two blogs and a small co-lab with a combined annual revenue of about $350,000…

The topic of insurance and “benefits” as a full-time freelancer is one that both fascinates and perplexes old and new friends alike.

“I could never leave my salaried job — I need benefits!” they exclaim.

“But what do you do about insurance?” they effusively inquire.

To which I usually reply, “Same thing Jeff Bezos does — I pay for it myself.”

I then pause for a moment to let my reply sink in.

Obviously, I am no Jeff Bezos.

And clearly Bezos is so rich now that his own company has taken over the responsibility of providing healthcare coverage to…

There’s no one-size-fits-all approach when it comes to setting professional boundaries in your freelance career.

For many, boundaries are a constantly evolving construct, ever-changing to realign with new goals and aspirations.

For instance, early on in my career, I had very few boundaries. I frequently pulled as many hours as I could and was constantly on call for my employers and my clients.

I was able to do so at the time because I felt it was a necessity to achieve my goals, and I had plenty of energy to work around the clock.

But in time, as one might…

I remember having a conversation with my husband about taking on a $10 gig on Upwork, a freelancer marketplace, shortly after quitting my job to become a full-time freelancer.

I worried I was selling myself short, despite the fact that the job was small and could be completed in well under an hour.

Not to mention the fact that the $10 would actually turn into $8 after Upwork’s 20% commission.

My husband, in his infinite wisdom, simply said, “Consider it a marketing expense. …

Asking for a raise is often a scary proposition, for both salaried employees and freelancers alike.

Some of us suffer from a bad case of imposter syndrome and worry that we just aren’t good enough or are undeserving.

For others, it’s a fear of rejection.

Sometimes it’s the discomfort talking about money in general — a taboo subject for many cultures and most traditional workplace environments. I remember at my last salaried job, my employer asked me to sign a contract where I agreed to never talk about my salary with my fellow employees.

Even after we overcome these fears…

In 2017, I quit my salaried job to become a full-time freelancer and never looked back.

Since then, freelance has become more than just a career — it’s become a way of life. And I never miss an opportunity to preach the freelance gospel whenever given the chance.

Luckily for me, when meeting new friends or striking up casual conversations outside of work, my freelance career often becomes a topic of interest.

While the motivation behind the questions I receive varies somewhat — with some inquirers trying to figure out if “freelance” is code for “unemployed” and others genuinely interested…

It’s every freelancer’s greatest fear — getting stuck with a “bad” client.

Most seasoned freelancers know how to avoid these less-than-ideal interactions before they happen by paying attention to red flags.

Red flags include when the client:

  • Is indecisive, non-committal and disorganized. A client who has a difficult time making decisions in the pre-hiring phase of the contract will often carry that same anxiety into the project.
  • Questions your credentials. While it’s always important to talk about your resume and experience, if the client seems suspicious about those credentials, it indicates a lack of trust. …

I remember being highly offended when my husband accused me of being a terrible employee.

We had been enjoying a glass of wine on the balcony of our high-rise apartment and reminiscing about how we’d gotten so far in such a small amount of time.

Three years prior, I had chosen to quit my job in the corporate world to work for myself.

Since that time, I had more than doubled my salary and moved to an apartment that I never would have dreamed possible in an affluent neighborhood in Miami, Florida.

Looking out into the Miami skyline, my former…

While researching this article, I was shocked by the abundance of editorials that rail against the practice. A quick Google search produces headlines such as “ Why Self-Promotion is a Terrible Idea “ and “ Your Self-Promoting Is More Annoying Than You Think .”

Even headlines that tout the benefits of self-promotion are laced with warnings of societal judgement: “ 5 Tips for Practicing Self-promotion Without Being Totally Annoying “ and “ 40 Ways To Self-Promote Without Being A Jerk .”

We all have that friend who thinks they’re the next Grant Cardone, who posts inspirational quotes, uses hashtags like…

Making the leap from a comfortable salaried position or steady paycheck into the world of entrepreneurship and freelance can be an intimidating proposition.

When I walked away from my full-time job almost four years ago, I was well aware of the risks involved, and I knew success was not a guarantee.

Fortunately, I was one of the lucky ones.

Within a few short months, I had already more than replaced that old income with revenue generated from my new freelance business. …

Morgan Overholt

Morgan Overholt is a freelance graphic designer and owner of Morgan Media LLC. She is also a contributor for Business Insider and Collective.

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