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6 crucial steps I took to quit my job and grow my freelance business to nearly $300,000 a year in revenue in just 2 years

Morgan Overholt   

6 crucial steps I took to quit my job and grow my freelance business to nearly $300,000 a year in revenue in just 2 years
Strategy6 min read
Morgan Overholt

QLC Creative

Morgan Overholt.

  • Morgan Overholt is the founder and owner of Morgan Media LLC, a graphic design agency.
  • After reaching a breaking point at her in-office job in 2017, she quit to freelance on her own.
  • Within three months of leaving, she made the equivalent of her 9-to-5 salary; now, she employs other people as part of her business.
  • Overholt recommends learning to sell yourself and using job marketplaces to find work.
  • Click here for more BI Prime stories.

In 2017, I made the life-altering decision to quit my "normal" 9-to-5 job and pursue a new career as a full-time freelancer.

Leaving behind the comfort of that guaranteed salary wasn't an easy decision. But the long hours and grueling demands of the corporate world were beginning to take a toll on my mental and physical health, so I knew I had to make a serious change.

It required a lot of blood, sweat, and tears, but in just three months, I was earning an income equivalent to the salary I left behind. In just two years, I more than doubled that salary with a freelance business that was generating nearly $300,000 in annual revenue.

Here are a few of the tips, tricks, and crucial steps that I took to break free of the corporate grind and become a six-figure freelancer.

1. Ignore the haters

The first and most crucial step in pursuing a life of freelance is to cast aside the negative voices in your life that say, "It can't be done."

It isn't entirely different from starting a diet or embarking on a New Year's resolution. If you go into it thinking that you're going to fail, you probably will.

Instead, spend your time in more productive ways: honing your craft, marketing yourself, and seeking the advice of already-successful freelancers.

2. Plan ahead

Admittedly, I more or less rage quit my last job. I had been toying with the idea of being a full-time freelancer for a while. I just had to reach my breaking point to finally work up the courage and take the leap.

Luckily, I already had a bit of freelance experience under my belt, which made the transition easier. I had been freelancing in addition to my full-time job for years as a means of earning supplemental income (to the tune of about $10,000 per year when I made the switch).

I also knew I had enough money in savings that I could use to pay the bills with for a couple of months in a worst-case scenario. At the time, my baseline monthly expenses were right around $6,000 per month (including food, utilities, car payment, and the mortgage). In addition to my investments and retirement account, I had about $20,000 in liquid savings - mostly money I had saved from freelancing part time over the years - which gave me peace of mind.

I never had to dip into that emergency savings account. But I would suggest to anyone considering the freelance lifestyle that they spend some time building up to it before making it their full-time career. Work a few nights and weekends and, if you can, stash some extra cash into a rainy-day account.

3. Learn how to sell

Learning how to become an amazing salesperson is a game changer.

I'm excellent at winning gigs because I know how to write a brief but well-worded proposal (I aim for 200 words or less - your clients don't want to read a novel) that stands out from the crowd and assures my clients that I am the best person for the job.

Each time I send out a proposal I include:

  1. The client's name - there's nothing in this world that makes a "cold call" feel even colder than using a generic greeting
  2. A list of my professional qualifications - mention your years of experience and a list of some of your most impressive clientele
  3. A demonstration of both my understanding of the project and interest in the work - clients recognize genuine interest when they see it
  4. A genuine kind word or compliment - compliment their branding, their product, their business model, their business acumen, their personality, etc.
  5. A link to my website for more information
  6. Relevant portfolio examples
  7. And most importantly … a call to action (i.e., "Reach out to me via email/messenger/phone and we can talk details.")

Here is a sample of a real cover letter that has been incredibly effective for me:

Morgan Overholt's sample Upwork proposal to attract clients

Morgan Overholt

A sample proposal Overholt sent on Upwork.

Knowing how to sell can also help you fetch higher rates. It's not about being the cheapest option available - it's about effectively communicating your abilities to a prospective client and giving them the confidence that hiring you is, without a doubt, the right decision.

Plus, learning how to sell is actually quite easy. There are plenty of articles, podcasts, and books on the topic. One of my favorites is "The Psychology of Selling: Increase Your Sales Faster and Easier Than You Ever Thought Possible" by Brian Tracy.

4. Hustle like your life depends on it

Nothing worth having in life comes easy, and a lucrative freelance career is no exception.

It is highly unlikely that you will become an overnight success.

When I quit my job, I was determined to make it on my own and did everything I could to avoid going back to the corporate world.

Shark Tank's Lori Greiner often says, "Entrepreneurs are the only people who will work 80 hour weeks to avoid working 40." And I have to say, especially in the beginning, that was 100% true for me.

I applied for multiple jobs every day. I exhausted every possible lead (old contacts, LinkedIn, Indeed, Facebook, networking events, conferences - you name it). In the beginning, I was regularly clocking 50 to 60 hours a week.

5. Take advantage of online marketplaces

I credit a large part of my success to online marketplaces, and they still comprise about half of my total revenue stream to this day. In fact, I've made over $200,000 on Upwork alone in just two years on the platform.

It's like fishing in a pond where you know the fish are biting. It will take time to earn your first gig - it took me two weeks to get my first nibble - but if you're a rockstar in your field, success is achievable.

The following strategies were the most helpful to me when it came to using these online marketplaces:

  1. Build a beautiful portfolio to show off to prospective clients that includes sample work, impressive mockups, and a link to your website for more information.
  2. Deliver a quality product to your clients - on time, every time.
  3. Ask for reviews at the end of every transaction and remind them that thoughtful reviews are a crucial part of your business. (I find the following note works: "Thank you! When you receive the end of contract notice be sure to include a thoughtfully written review. Reviews are a very important part of my business. Let me know if you need anything in the future!")
  4. Ask your clients to keep you in mind for future work and/or referrals.
Morgan Overholt's graphic that her company created for the CDC Foundation

Morgan Overholt

Overholt, who's worked with the likes of the CDC Foundation, sends samples and posts on Upwork so her clients can see the caliber of her work.

And yes, some of these sites charge fees to use their services or take a percentage of your earnings as commission. But even a 20% commission means an 80% profit margin for the freelancer. Most retailers would kill for those kinds of numbers.

6. Don't be afraid to scale your business by hiring help

A year into running my solo freelance business, I found myself with more work than I could handle. It forced me to make a decision: I could start turning down jobs, or I could hire help.

Scaling my business by hiring other freelancers to work under me was one of the best decisions I've ever made. It almost immediately doubled my revenue and improved my quality of life by taking some of the workload off my plate.

Before I had help, it was difficult to take a day off. And taking a vacation meant losing an entire week's worth of income. Today, I can take a day off with the peace of mind that the business is still generating income, and that my right-hand woman is holding down the fort and taking care of my clients.

Now I employ one full-time employee and three part-time contractors. Each one of my freelancers also has their own specialty - branding, illustration, and print work - which has allowed me to take on jobs that would normally be beyond my solo abilities. And my clients also seem to appreciate that someone will always be available to take care of them, even if I am not.

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