I’d put it off for too long…

From the moment I started work at my first full-time marketing job, they knew I had one foot out the door.

I’d been clear in 2005 that I intended to eventually become a freelancer.  And my boss told me that he wanted to keep me so happy that it would be hard to do.

Well, he succeeded.  So even as I started doing freelance projects on the side through 2006, 2007, 2008, and 2009, I still couldn’t manage to actually break free of the J-O-B.

Frankly, I was both happy, and miserable.

I was happy because I knew I had just about the best gig I could imagine.  I had managed to establish myself well enough that I made most of my own rules.  I created my success there.  And I’d gone from making $20k per year to somewhere around $80k, in less than half a decade.  Plus the work environment was super casual, with sushi lunches, Nerf fights, major flexibility, great benefits, and more.

I also knew two things about what would happen when I moved on.  First, it would be almost impossible to replicate that job experience — nearly anything would be a step down.  And I also knew that if I actually took any kind of job, I would be miserable because I would have “failed” at my dream of becoming a freelancer.

So I became comfortably numb to it all.

I did some freelance work.  And I did my job.  And I continued to do well.  All the while knowing that I wasn’t really living the dream, the desire, the destiny I had for myself.

Then — the breaking point…

We’d been living in Oregon since 2005, so my wife could get her Ph.D.  In 2010, we’d have to move somewhere else — preferably to the Midwest to be closer to family — in order for her to do her internship year and finish her degree.

That meant I would actually have to ditch the job and do something.

Not only that, we only expected to be in our next location for a year.  So even if I showed up at some new job ready to go, it would be unlikely I’d be able to build up the kind of credibility and relationships I’d need to really thrive, until it was about time for me to move on again.

Which meant I’d probably take a major step down in income, job satisfaction, and opportunity — unless I made the freelancing thing work.

My back was against the wall.

I had to make a decision.

I still didn’t feel 100% ready to go full-time freelance.  I figured I probably had the skills.  But I didn’t have all the client relationships and workload that I thought I’d need to succeed.

That said, even if I tried and FAILED, that felt like a better option than just resigning to my fate of some mediocre job.

So I made that difficult decision.

I decided I’d try freelancing.  I’d let the network I’d started to build know what was going on.  I’d find new ways to connect to them.  And I’d see if I could get it rolling.

Oh, and by the way — not only was my wife getting the low-level pay commensurate with an Internship, we had a new son who was less than a year old, and we still had a mortgage.  We’d saved up a few months’ worth of expenses in a rainy day fund, but I didn’t really have an option…

I had to make this work…

I’ll tell you what came next in a just a second.  But first, I’ll state that this article is a bit of a Mailbox Monday article, on a Tuesday.  The queue is long enough that I wanted to write an extra article to clear out the question.

So before I get into what happened next, here’s the question that prompted this article — and the advice that follows.

Hi Roy,

I’ve studied copywriting for years, reading all the classic texts, plus I’ve taken a couple of AWAI courses. A couple of years ago I was able to apprentice directly under Joanna Wiebe of CopyHackers (for one year).

Since then I’ve had a couple of independent freelance jobs but I’ve found it tough to maintain momentum on my own, as throughout all of this I never stopped working a demanding full-time corporate job. (And I’ve not been able to figure out how to balance client demands while working full time.)

Looking ahead, I’m about 8 years from retirement, and I’ve been thinking I’d like to transition to full-time freelancing at that point.

What might you recommend as a viable path forward, so that I can realistically (and profitably) transition to freelancing when I retire?

It’s 8 years out, which is both a blessing and a curse. It’s far enough away that it’s easy to ignore. But I also don’t want to be so “out of the game” by then that I’m effectively starting from scratch.

Thanks for your thoughts,


Here’s the thing — I wasn’t ready to transition to freelancing, until I made that decision…

I was “at threshold.”  This is a principle I got from Mike Mandel, who is one of the world’s foremost teachers of hypnosis.

Basically, you’re at threshold when all three of these things are 100% true for you…

— Something has to change.

— It has to be me.

— It has to be now.

I spent years before this dreaming of the day I’d become a freelance copywriter.  And frankly, I probably had two of those three things in the bag for most of that time.  I knew in my work situation that something had to change, and it had to be me.

But the difference between all those years from 2005 to 2009 and the next year, 2010, was in the final statement: it has to be now.

As soon as I realized that the time had come, I did everything it took to make it happen.

I’d been developing the capabilities and relationships for years.  I just didn’t make it happen, because I didn’t need to make it happen YET.

Then, as we approached 2010, it was time.

We were looking forward…

We’d be moving in the summer of 2010.  It was late 2009.  And by the time we were moving, I had to quit my job and decide what to do next.

So at the very end of 2009, I attended AWAI’s Bootcamp.  (They used to be in November!)

By the time I got home, I was ultra-clear.  I made plans.  Then, I gave myself a date: March 1st.

That would be my “Personal Independence Day.”  The day after which I’d never set foot in an office as an employee again.

Yes, I had a fall-back plan.  First off, we had enough cash to cover about 5 months’ expenses, even if I wasn’t making anything.  (Including our summer move.)  But also, if I couldn’t get traction by the summer, I could seriously start looking at job opportunities for when we arrived in our new location.

Well, I didn’t need the fall-back plan.  The simple act of making that decision and setting the date was even more effective than I’d hoped.  (That’s the power of being at threshold.)

I had clarity of vision.  Which is one of Dan Kennedy’s Wealth Magnets.

I reached out to my network.  I told them of my plan — and availability to take on projects.  Suddenly I had agreements for multiple projects.  I was in-demand.  I was booked.  And I actually needed to start EARLY.

So at the end of January, I gave my two-week notice.

I told the owner of the company I needed to talk to him, in a private conference room.  As he closed the door, he asked, “You’re not quitting, are you?”

And with complete confidence, I said, “Well, actually…”

And two weeks later, I walked out of that office for the very last time as an employee of the company.  And although I’ve been on retainer with clients since then, I haven’t worked a traditional office job since February 11, 2010 — my Personal Independence Day.

The power is in the decision that it’s time…

I don’t want to discount some of the other factors, such ask skill and having a basic understanding of how to run a freelance copywriting business — the topic of my book The Copywriter’s Guide to Getting Paid and The Freelance Copywriter’s Independence Package.

But the reality is that if you can put it off, you will put it off.

And so in response to the question above, I’m pretty certain that’s what’s going on.

I know Jo at CopyHackers, and I know that if you’ve worked under her for a year, you have all the chops you need to do the skill of copywriting.  I also know the business side isn’t that hard, and if you’ve had a few independent jobs plus survived in corporate for most of a career, you have enough capability to get started and get better as you go.

So basically you’re in that same situation I was in, in my first and last marketing J-O-B.

You know where you want to go.  You probably have everything you need in your toolbox to get you there.  But you’re okay enough with your current situation that you’re not forced to make it happen yet.

If that changes and you really want to make it happen, the first thing you should do is make sure you have a clear start date set on your calendar, and let everybody know who might be able to offer or connect you with opportunity.

In the meantime, here are three more simple recommendations to make sure you cover.

— Save money.  Not “retirement” money.  But something like “rainy day” money.  Money that you can spend if absolutely necessary, when you’re making the transition.  But also, money that you really, really don’t want to touch if you don’t have to.  Being desperate for money in the first few months of your freelance business will work against you, so having a cache of cash will serve you very well.  (I am a huge believer in hoarding cash so I’m never beholden to whomever can offer me the next check.)

— Keep doing small side gigs.  This keeps your skills fresh.  It keeps you connected.  It maintains momentum.  You can afford to have more space between these, and keep them smaller, because they’re not your primary income.  But it’s important to keep doing them.  Because they will mean you’re ready to go when you want to make this full-time.  They can also help with the first point (extra cash) and the next point (relationships).

— Cultivate relationships.  Sounds like you’re already doing this.  Keep it up.  Go to conferences, as you can.  Meet people.  Work with a few different clients.  The idea is to have a solid address book of people who you can reach out to when it’s time, who will know who you are and what you’re capable of.  One or two good client relationships can make all the difference between an easy and a really difficult start to freelancing.  (I had established a relationship with AWAI, and they were responsible for about 70% of my income my first year.  The other 30% came from clients they connected me with, or that I was able to connect with on my own, because of working with AWAI.)

It’s really pretty simple.  But these simple truths are among the most powerful pieces of advice for anyone looking to be ready to transition to full-time freelancing, whenever you finally decide that “it has to be now.”

If you don’t yet have a copy of The Copywriter’s Guide to Getting Paid, here’s where you can get it free (just pay S&H) and get even more insight into building a successful freelance business.

Yours for bigger breakthroughs,

Roy Furr