It’s Monday — that means it’s time to open up the mailbox and answer YOUR questions!

What I’m about to tell you is incredibly simple — but not necessarily easy…

So it goes with many great things in life.

Actually doing it isn’t that complex.  It’s a series of actions you need to take.  Or some words that need to come out of your mouth.

But the thoughts and feelings you have to deal with to make it happen are a much bigger roadblock than the process of taking the action.

If you bring yourself to taking the simple actions though, you may find the outcome comes easier than you feared.

So I’ll answer today’s Mailbox Monday question with the hope of getting you to take those actions…

And if YOU have a question you’d like to see answered in an upcoming Mailbox Monday, simply click here and submit your question.

Today’s question…


How should I approach companies that I have worked for in the past as a copywriter?  I have expertise in the content and concept of what industry they are in but no specific sales letter experience.

Best regards,


Let’s start with the why, then we’ll get to how…

First, I’ll admit that I’ve never really done this.  Although I do know copywriters who have, and understand why to do it.

In fact, I see two major advantages of approaching old clients for copywriting work.  The first is relationships.  The second is that you have insider knowledge.  I’ll speak to both in turn.

A tricky element of client work isn’t necessarily doing the work.  It’s the unpredictability of the human element, and how two human beings that don’t know each other will get along and accomplish things through cooperation.  By working with old employers who you know and have a relationship with, you are presumably in familiar territory.  At least you know their foibles and they know yours.  Even better, if you liked them and they liked you, you’re starting on good terms.  That’s great!

Also, insider knowledge of the business and industry is powerful.  In fact, understanding how a market works and thinks is highly-useful when it comes to writing copy for that market.  This is part of why the best copywriters in the world specialize in just a handful of markets.  (If not just one.)  In essence, by working with old employers, you’re not starting at zero in the industry, which is a huge advantage in communicating in their voice and with their market.

At least in theory, these two factors provide a huge advantage, and suggest that this is worth pursuing.

So, how?

Here’s how to turn your old employers into new copywriting clients…

In short, ask.

To make it slightly longer, ask honestly.

I’m going to make the assumption, for the purposes of this answer, that my friendly correspondent is fairly new in pursuing copywriting.

From that perspective, here’s a pretty good sketch of an email, letter, or phone script that could work…

Hi Jane,

It’s been a while.  I hope you’re well.

I’m reaching out because I’ve started writing marketing and promotional copy for businesses, to help them get more leads, customers, sales, and profits.

And I thought of you and Acme, Inc.  After having worked with you at Acme, I feel like I have a pretty good understanding of the market and your customers, and can speak to them in a clear and compelling way.

I was wondering if you have any upcoming marketing campaigns or other promotional copy needs we could speak about.

You can actually schedule a call with me at this webpage: [I’d insert a Book Like A Boss link here.]

We can chat about any needs you may have, and I can answer any questions you may have about this new direction in my career.

I look forward to speaking with you.

Best wishes,


That’s all VERY generic and I’d definitely insert a ton more personal detail into it if I were doing it.  And it’s in a very soft corporate voice, whereas if it were actually me I’d add my own personality into everything.  (I probably also wouldn’t refer to it as copy unless I knew it was common language the recipient really understood.)

That said, it gets the IDEAS across.

— I’m doing something new.

— I think my new thing could benefit you.

— Let’s talk.

If I’m reaching out to a bigger company I’d worked with in the past, there would also likely be a networking step or two added in here.  Let’s say I had to reach out to my old boss, to figure out who the best contact would be.  I’d do that, asking who ran marketing communications.  Assuming they knew, I’d start my note with a reference to that connection.  Or if it was an even bigger company, once I figured out the best contact I’d simply make reference to what business unit I worked in.  (The bigger the company, the more likely it is that the relationship bit no longer matters.)

After all this, I’d like to take a brief detour and tell you…

Why to skip this and go for new clients instead…

I imagine you’re asking this question because somewhere along the line someone gave you the idea that it would be easier to work with a past employer.

And if you’re still interested in the market, left on really good terms, and really want to be working with that company and serving their customers, this might be a great opportunity.

That said, if any of the above is even a little untrue, think again.

This might NOT be a very good opportunity.

Because we move on.  We develop new interests.  We get excited about new things.  And things that worked splendidly in the past could be a dismal failure if we tried to revive them.

Let’s imagine I tried to revive my DJ career.  Playing night clubs until last call, and performing at clandestine all-night dance parties at sometimes-questionable venues.  Something in my life would likely suffer, if I did actually make that work.  And it’s quite possible that because of who I am now, I wouldn’t get the same level of interest from that audience.

There’s some advantage to always looking forward.  Change is the only constant, and trying to hold onto the old while living in the new can create unnecessary complexities.

For example, the question specifically says “no sales letter experience” — but says nothing as to whether or not these companies are actively hiring copywriters to write sales letters.  If I were to approach pretty much any of my past employers to get them to hire me to write the kinds of sales letters I write today, at my current fees, they’d laugh me out of their office.  Because it’s so contrary to what they do.  Whereas my new clients are happy to pay my fees, consider them to be a bargain, and want exactly what it is that I offer.

Unless you worked for companies that hired copywriters but outside of the marketing context, and are now trying to get back in with them inside the marketing department, you may find that a tree that’s not really worth barking up…

But I’m not going to end on this note…

One more way to make the most of your past employment relationships…

Let’s imagine for a minute that you’re thinking twice about working with your past employers.

But you still want to leverage the relationships you’ve built.

In this case, you simply reach out without asking for them to hire you directly.  This is a classic active referral marketing strategy.

“Hey, I know you and you know me.  I wanted to let you know what I’m up to now.  Here’s what it is.  Do you know anyone who’d be interested in this?  Specifically I’m thinking people who meet X, Y, or Z criteria.  If so, would you be willing to take two minutes to introduce me to them?  Gratefully, Me.”

You get the point, I hope.

The value of your relationships doesn’t stop with the people you have that direct relationship with.  Everyone you know also knows people, who know people, who know people.  And if you’re proactive and kind with this, you can quickly expand your network in any direction you’re intentional about.

Oh, and this can actually be a sneaky way to gauge their interest.  Because if you tell me you’re doing something that I might need and you ask if I know anyone who needs it, I may just turn around and hire you without you ever asking directly.  Which makes this a pretty good prospecting strategy on its own, without having to be very direct about it.

Yours for bigger breakthroughs,

Roy Furr