Beach Bum Income


The Phases of a Successful Freelance Career

I lost my lucrative instructional design job 10 years ago. It was one of the worst — and best things to ever happen to me.

While job hunting, I started selling my services through Elance. (Elance merged with Odesk and became Upwork.) It wasn’t easy. Between finding and bidding on jobs, taking low-paying gigs that took too much time, studying experts, and reading how-to books, I spent over 50 hours a week learning how to be a freelancer. Good thing I didn’t have a job, right?

Fast forward to today. I now make double the income I had on my former job, and I work literally 10 days per month. That’s not hyperbole. It’s by design.

But it didn’t start that way. Before I reached my current level of wealth, I went through at least 5 phases of freelancing growth.

The “Freelance Everything” Phase

My first 4 years of freelancing felt like a constant struggle. I celebrated gigs that paid $3,000, but those were rare, so I still had to take gigs that paid $100 – $300, and often took gigs at $50 or less, just to prove myself to a new client.

I had a large mortgage to pay, and didn’t want to lose my quality of life, so I had to work a lot to make enough money. What work did I do? Mostly ghost writing ebooks, writing articles, and writing reports. But I also dabbled in graphic design, transcription, and sales.

Fortunately, I found Fiverr in it’s early days, and that had big benefits for my freelancing future. In the beginning, I was able to sell trickle of gigs for writing reviews, writing ultra short blog posts, putting santa hats on people’s logos, etc.

But then something magical happened with Fiverr…

In those days, Fiverr was still promoting individual gigs on Google Adwords. One of my gigs was sponsored and it turned into a $800/month stream of income. I didn’t know what was happening, but suddenly five to ten gigs were coming in every day! And get this…I was fulfilling a pre-made gig. I literally pushed a button to fill the order. It was truly “easy money.” I still run that gig today. It doesn’t make that much money any more (I’m not promoting it with adwords), but it’s still pulling around $300/mo. I plan to hand it off to my son when he goes away to college.

Unfortunately, Fiverr no longer does adwords. To make big money on Fiverr, you have to be very smart about it. One good thing…with changes to Fiverr, you can now make as much money on Fiverr as you can on Upwork, depending on the kind of work you do. It’s not uncommon for people to be making $5,000/mo. or more from Fiverr. If you’re interested in making a real living from Fiverr, see this post to start.

Also, if you’re planning to market yourself on Upwork, plase use my winning bid proposal template here.

So that was the start of my freelancing career. It was a lot of work, but the worst part about it was the uncertainty. I knew I couldn’t keep this up for the next 20 years of my life.

The big change in my freelancing career happened when I admitted I wasn’t ever going to get my lucrative former job back. That’s when I started taking a different view of my freelancing, realizing I had to consider it a business, not a thing I was doing on the side until I got a “real” job.

I stopped searching for freelance gigs and started researching online businesses. There’s a fine line between freelancing and doing an online business, especially when you’re doing the same work in both cases. I think the difference is in how you look at what you do, not so much what you call it. A business perspective makes you look at more angles, plan ahead more, think about the big picture, put more structure and systems to it.

The “Instructional Design Business” Phase

Because I was already an expert instructional designer, and a lot of my freelance assignments were how-to ebooks, I decided to start my own instructional design business. I planned the whole thing, from office space to capital investment. Created letterhead and cards. Even landed two high-paying design gigs that kept me comfortable for a few months at a time while I built the beginnings of the business.

By the way, there is plenty of work in freelance instructional design. Many corporations now want to outsource that work rather than hire an in-house designer. If you’re interested in instructional design freelancing, contact me.

I soon found myself attracting a particular type of client: Designing training programs for guru authors. It was fascinating work that paid well, but it involved a lot of babysitting of said gurus. I also found it hard to imagine doing that non-stop for the next 20 years of my life.

Fortunately, my experience with guru authors led to the next phase of my freelancing career.

The “Ebook Authoring” Phase

One thing you learn quickly as you work with authors is that it’s not difficult to be an author. These days, with Amazon, anyone can be an author. It’s better to be a good author, but anyone can do it. I decided I had several books in me that I wanted to share with the world.

So I began my ebook authoring phase. To see how “easy” this was, and how I profited, see my post on Writing Ebooks and Reports for Profit.

That was my first taste of passive income, and I realized that I never wanted to go back to trading time for dollars. I imagined writing a book a month, eventually building up to 200 or more books. I may still write more, but after publishing my seventh book, I suddenly had an epiphany.

The “Subscription Business” Phase

I was putting all that content into a book that was selling for around $2-8 per copy, when I could put that content into a newsletter and sell it for $9-20/month! That was the start of my subscription business…and I’ve never looked back.

My subscription business is what earns me the big bucks today. Oh, my books still bring in a trickle of income each month, and it’s 100% passive. I haven’t logged into Amazon to look at my book reviews in over 2 years. The reviews must not be too bad, because I keep getting paid a few hundred dollars every month.

The best thing about my current subscription business is that I literally work 10 days per week on it, giving me plenty of time to do what I want in life. I spend a lot of time with my family, I don’t worry about money, and I get to play with new businesses Ideas.

So the next phase of my freelancing career was less about making money and more about following my passion.

One thing to know about me is that I love PASSIVE INCOME. So running live webinars is not my thing. Live coaching is not my thing. Public speaking is not my thing anymore (I spent years on the road as a platform speaker…been there, done that). These days, I love helping people build a freelance career that moves gradually towards passive income! That’s my passion.

The “Online Teaching” Phase

Teaching online courses is a lot like authoring ebooks.

You create an effective video course, post it on a site like Udemy (which does most of the marketing), and collect a passive income. The downside for me is that I take too long on the technical aspects of that work. While a makes a tiny trickle of passive income each month, I have a lot to learn about the online teaching business. I include it here as a phase of my freelancing career, because I suspect it will grow as a part of my blogging platform.

Which brings me to the most recent phase of my freelance career: Blogging.

The “Blogging” Phase

Beach Bum Income is not my first blog. I have several blogs that keep my subscription businesses high in the search rankings. But this is my first blog just for me to give back, to enjoy teaching others how to create a freelance lifestyle, and eventually a passive income.

Here’s where I get to share what I’ve learned, listen to your stories and problems, and offer advice. I’ll suggest resources that I’ve tested and proven. And you can always contact me to get answers.




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