10 years ago TODAY, I walked out of my last job, for good…

A decade!

Seriously, that seems a little strange.  It feels like forever ago, and also just yesterday.

I quit my job.  No more cubicles.  No more 9-to-5.  No more heavy-handed boss whose bad mood had the potential to wipe out my salary and lifestyle (that was a REAL worry with the owner/entrepreneur who was running that company, although thankfully not my direct boss).

Since then, all the trappings of entrepreneurship — running a copywriting, consulting, and publishing business.

Yes, plenty of freedom.  I control my schedule.  I work when and where I want.  And I have the potential to make a lot more, based on my success (and I have).  Plus, I get to pick and choose my projects — which, recently, has involved significantly reducing client work in favor of publishing.

But also, 100% complete and total responsibility for my success and failure.  Which, admittedly, I’m still getting used to.  No boss to help me get back on track.  Nowhere else to defer blame when things aren’t going well.  Oh yeah, and health insurance costs!

It’s not always easy, but I wouldn’t give it up for the world.

And I’m often asked how to make the transition.

So today, in celebration of my “Personal Independence Day,” I’ll share some helpful stories and ideas.

First things first…

Get crystal-clear about your vision…

I discovered copywriting in 2005.  I learned about freelancing at the exact same time.

I KNEW it was for me.

I hadn’t really known what I wanted to do for a career before that.  But I did know I wasn’t going to spend my life working in a cubicle farm.

When I discovered freelance copywriting, I quickly realized it was a very direct path away from the cubicle farm.

And yet…  I DID NOT start my client copywriting business at that point.

I knew: I didn’t know what I needed to know.

And I also knew that I could embrace a few years of full-time employment to learn the ropes of marketing and entrepreneurship, to dramatically increase my likelihood of success when I went out on my own.

So, that’s what I did.

Even as I held this crystal-clear vision of entrepreneurship and the client copywriting business I wanted to build, I focused first on getting good at some of the core skills in a 9-to-5 job.

It was in service of this greater vision.

So I took a job.  I got to practice marketing and copywriting.  I got real-world experience in a relatively entrepreneurial company.  And I had some stability, plus was getting paid to learn.

It actually turned out to be better than I’d hoped.

The boss’s bad moods notwithstanding, the workplace was pretty cool.  I quickly grew my income, and my contribution to the company’s success.  We had a lot of fun, while working hard.  And we had all the benefits of a Silicon Valley workplace, a few hundred miles north in Eugene, Oregon — we had free sushi, Nerf wars, flashy tech, fully-paid health insurance, competitive pay, and more.

I did spend time in a cubicle.  But the office was not quite the cubicle farm I dreaded, and there were lots of perks.

Because I had a clear vision, I really thought I would only be there for a couple of years.  They managed to convince me to stay for 4 1/2.  Until I was a few months away from moving across the country, as my wife was finishing grad school.  And I could use that as my excuse to finally make the leap.

And yet, I had kept my vision of my client copywriting business in the front of my mind that whole time.  (Even though it took me longer than expected to actually do it.)

And I wasn’t sitting on my hands — fat, dumb, and happy from my full-time job…

Learn to get and serve clients…

Within a couple years of starting that full-time job, I was getting itchy.

I KNEW I wanted to work freelance.

I also KNEW I wanted to do direct response, which was not a focus there (though I figured out I could use direct response principles and strategies, if not some of the more common techniques such as long-form sales letters).

So by 2007, I was approaching clients.

(This is the story I tell in the Appendix to The Copywriter’s Guide to Getting Paid.)

I got my first client, and did pretty well.

Then, I did some more.

Early on, it was more about learning the process and getting some experience than it was about getting paid.

Because I had the full-time job, I could be relaxed about my income.  Which actually served me really well in forming good client relationships.

I also had enough experience through my full-time gig that I was able to aim a little higher with client work.  So even early on, I could skip some of the bottom-feeders that target novices on freelance job sites.

I made plenty of mistakes.  But because I was still working full-time, I had the flexibility to recover without it hurting my family.

(Oh yeah, and long before I went full-time freelance, I had all the legal and administrative parts of running my business worked out.  Another perk of doing it this way.)

This is what Mark Ford (aka. Michael Masterson) calls “chicken entrepreneurship.”

You start your business on the side of whatever else you’re doing — whether that’s a full-time job, or another business.  And only as it provides enough income and demands more attention do you transition into the business.

Build up a “rainy day fund”…

If you’re serious about quitting your job and starting your business, you don’t need to replace your current income before you do so.

But you do need to build your income and momentum to the point where you know you can make consistent income from this new venture.  And that if you put in a full-time effort, you can increase your income to what you need to live as you wish.  (Preferably, even better.)

But there will inevitably be a transition.

And if you’re going from consistent income to the inconsistencies of entrepreneurship, you need to be ready for that.

I strongly recommend a rainy day fun of a MINIMUM of 90 days’ expenses.

This means you could live for 90 days without making another penny, and not get behind on any bills or obligations.

Better if it’s more.  6 months.  12 months.  But 90 days minimum.

And then aim to never touch that money, and only build on it.

(I do the same in my business, even today.  And my personal finances give me even more flexibility — that I don’t want to touch as long as I’m still earning a living.)

…  Oh, and I’ll note: I was doing this in 2009.  I had a mortgage.  My wife was a grad student, with relatively small income.  The economy had just crashed.  We were planning to move halfway across the country the next year.  And our oldest son was less than a year old.

All of that said, once you have this financial cushion, you have to act…

Set a specific date…

As long as you keep this as something you’re going to do at some point in the future, you won’t do it.

You have to dedicate yourself to taking action.

And the way you do that is to schedule it.

Put a date on the calendar.  Give yourself a couple months to ramp up.  I think I gave myself 3 months.

Then, start reaching out to the clients you’ve worked with, and others in your industry.  Tell them what’s going on.  Share your plans.  And start filling your calendar for after the date.

You’ll be creating obligations that require you to move forward.

You’ll also be creating momentum.

I was able to go from full-time employment to fully-booked using this method.

I took a long weekend between the two.  But I had a full load of client work from the day I officially started full-time in my client business.

Feel the fear and do it anyway…

This is a powerful mantra.

When you are 100% responsible for your success and failure, you will feel plenty of fear.

That’s normal.

Even good.  Because fear means you’re stepping outside of your comfort zone, out of the ordinary.  And it’s only by going beyond the ordinary that you become extraordinary.

Don’t stifle fear.  Fear helps you see challenges clearly, and respect the difficulty.  Feel the fear and radically accept it.

But you CANNOT let it rule you.  Don’t run from it — run towards it.

When you feel fear, double-check that you’re doing the right thing, and then do whatever it is that is making you feel that fear.

Here, I’m referring to that day where you finally quit your job.

I still remember quivering with fear, anxiety, and a load of excitement when I told my bosses that I was giving my two-week notice.

And starting that first day of work on my own was terrifying.

But now a decade later, I’m immensely grateful to my past self for taking action in the face of fear.

Recognize that the darkest nights and the brightest days are yet to come…

Here’s the thing about entrepreneurship  and starting your business…

— It’s FAR HARDER than most people think.


There will be moments in the future where you just want to throw in the towel.  Where you’re stressed emotionally, rationally, financially, and more.  Where you just want to give up.

And because of the nature of entrepreneurship, they will be much harder than they would be if you were working full-time for someone else.

But when you build something that’s bigger than yourself, and it comes from your vision and is created in the world, that’s also far more rewarding than serving someone else’s vision.

Entrepreneurship and starting your own business — whether it’s a solopreneur client business, or something much bigger — is NOT for everybody.

It takes toughness, grit, perseverance, mental and emotional strength, resolution, determination, and a whole pile of character.

And even if you think you have those qualities, it will demand far more.

Embrace the obstacles, the challenges, and the resistance you face…

Entrepreneurship is fundamentally a creative endeavor.

And like any creative endeavor, it stimulates a whole pile of resistance in whomever undertakes it.

It will throw obstacles and challenges in your way.

You’re forging a new path.

Embrace the difficulty.

Know that others gave up at the previous obstacle.  And more still will give up at this one.  And yet more still will give up at the obstacles to come.

Those are your competitors.

Success often simply takes overcoming ONE MORE obstacle than the next guy or gal.

So embrace them, knowing that with each one your field of competition grows a little smaller.

And with every obstacle, you’re learning, and growing the strength of character for ongoing success.

Yours for bigger breakthroughs,

Roy Furr

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