The Born Freelancer on the Five Phases of Freelancing

This series of posts by the Born Freelancer shares personal experiences and thoughts on issues relevant to freelancers. Have something to add to the conversation? We’d love to hear from you in the comments.

the born freelancer

The Five Phases of Freelancing

In this post I thought it might prove useful to look at the multiple phases of freelancing and what one might realistically expect from each.

I’ve arbitrarily designated five distinct phases but you could infinitely subdivide that number to achieve greater specificity. By necessity I will present generalizations and composites of each career phase. I’ve described them in terms of occurring in order from youth to maturity but each phase could begin or end at any time.

Phase One: The Wannabe Years

They bring a wry smile to my now slightly world-weary face. They’re full of frustration and yearning to just get into the business! At times such a leap seems impossible. Doors are firmly closed, and you are repeatedly told to come back only when you have experience—but how can you get experience if nobody will let you get it?

In reality, this is a wonderful time in which to study, to learn, to play around with your skill sets and develop as wide a range of interests as possible. There are no deadlines to meet, no editors to placate, no bank accounts to keep filled. Your only limitations are your imagination and your willingness to learn.

At this point you may not even contemplate freelancing as a lifestyle (although many of us, already prejudiced against a more conventional choice of careers, did so at an early age). You may view it merely as a method of getting a foot in the back door of your chosen profession (such as writing or broadcasting).

Phase Two: The Rookie Years

These years combine the “best” and the “worst” aspects of freelancing.

First, the best. It is exciting! You will never forget the hustling, the endless interviews, auditions, spec submissions and resume-padding. If lucky you may find a helpful mentor. Your first real freelancing job will forever burn brightly in your memory as the crossing-through-the-looking-glass moment from Wannabe to Rookie that you’d always dreamed about. Oh sure, it may be negligible (in truth) but it will be a triumphant occasion for most.

And now, the worst. Progress will be unsteady. You’ll get one freelancing gig and then weeks or months may go by before another turns up. (Better get used to it!) You may have self-doubts and your mental health may take a beating. Some may decide that taking up dentistry wasn’t such a bad idea after all (like their parents said). Others will double down—having once inhaled the sweet smell of success—and will forever be hooked.

A few clients may take advantage of your need to get experience and will give you the worst jobs at the worst pay. The trick is not to be so proud that you refuse them but to do it all with an integrity and budding-professionalism that will get you noticed. You will eventually begin to get more work, more recognition and (we hope) more money. (Of course, if money is your primary goal, you will quickly learn that there are better ways of making it.)

Phase Three: The Journeyman Years

(The term “Journeyman” is used here in a non-gender-specific way.)

In this phase, you will find freelancing work on a regular basis but it won’t always be the exact thing you want to do. And when you do get it you won’t know for sure when the next freelancing job will come along. (It’s sort of like that old joke, it’s lousy food and such small portions too!) Many will need to supplement their freelancing with regular or temporary part-time work.

Your reputation will grow and employers will get to know you are trustworthy and reliable. You will no longer choose to work “on spec.” You will continue to promote yourself using whatever platforms you find appropriate. You will continue to upgrade your skill sets whenever the opportunity arises. You will join professional guilds and learn how to negotiate successfully and also how to turn down unfair clients.

This is usually the point of no return: Do you continue freelancing or do you go part-time or even give it up? You may get offers to jump to a more conventional but related nine to five job such as PR. Many will jump. It’s not easy to live with the ups and downs of a freelancing income especially if by now you have a family and other commitments.

Those who persevere and carry on freelancing may do so for longer than they expect during this phase.

Phase Four: The Silver and/or Golden Years

The dream is that eventually you will gain full control over what you do and when and where you do it. In reality, all freelancers know that most of their career will be decided by a combination of good luck, rigorous networking and hard work.

A chosen few will enter their Golden Years. You will have control, your reputation or brand of choice will become well known and secure, and continuous work will allow your income to be stable and enable a comfortable if not spectacular life. You will save like crazy for the “rainy days” that are sure to come…one day.

Most who enter this phase will have found fufilment and a real sense of connection with their work. Freelancing will provide not just an income but the very type of lifestyle, free from the constraints of a nine to five job, that will define and characterize who you are and how you wish to live.

A slightly diluted version of this may be deemed The Silver Years in which everything is as it is for those experiencing The Golden Years but there will always be less of it and more constant scrambling and hustling. These are the years most of us will encounter and find no less enjoyable or worthwhile.

The worst aspect of this phase is that you will never really appreciate you are in it until it ends.

Phase Five: The Emeritus Years

It’s hard to say when this phase will begin.

It is easier to say it will begin when you least expect it.

You’ll be going along, working, networking, happily complaining and then one day…the work requests and the returned phone calls, one by one, will stop.

Hopefully you have saved up enough to cushion the blow.

Your regular clients may be retiring or moving on (often becoming freelance consultants themselves). The venues you worked on may be sold or changed and new owners may not perceive your continuing value.

Younger, less expensive, less experienced freelancers will now be competing for your gigs—and often successfully too.

And so you now need to reposition your brand to take advantage of your experience and promote it as a positive—and not a negative.

If you are so inclined you may also choose to teach or at least to mentor a rookie or two, giving back some of that which you have gained.

See my earlier posts on Ageism and on Teaching for more ideas.

I’m not sure the true freelancer ever actually fully retires. There always remains (to some degree or another) the hope of one more assignment, one more kick at the can, one more chance to share what we’ve learned in a lifetime of learning and sharing.

The Takeaway

This may have read like a rather negative assessment of freelancing—when in reality it is the ideal choice of career and lifestyle for many of us. If I had to do it all over again, I would choose freelancing again without hesitation. But there is nothing wrong with doing so with eyes wide open, and making yourself aware of the pitfalls and shortcomings (past, present and future) as well as the more obvious advantages and benefits. That has been the purpose of this post.

Freelancing requires a certain toughness and duality of mind. You can dream dreams and make them come true but you also must live with your feet firmly on the ground and be well versed in the necessary life skill sets in order to survive let alone thrive. Most folk lean heavily towards only one of these seemingly contradictory paradigms. It is the rare individual who can successfully embrace both with equal ease and ability. They are a breed apart.

They are called freelancers.

Posted on March 6, 2023 at 6:00 am by editor · · Tagged with: ,

Leave a Reply