how to know which mentor is right for you

So in my last post I talked about shortcuts and magic pills, and how they’re rarely the instant boost they claim to be.

And then I shared my personal shortcut – mentorship.

Now, mentorship doesn’t negate actually showing up and doing the work… but a good mentor can help DRASTICALLY shorten the learning curve (and potentially prevent you from bashing your head into the wall… like yours truly did, several hundred times).

I had a couple people reach out privately to ask how exactly a mentor-mentee relationship works… so today I wanted to share a few examples of how I’ve seen it work in copywriting/marketing.

NOTE: this is just me speaking from my personal experience. Your mileage/experience may vary.

Typically if you’re looking for mentorship or guidance as a copywriter, it might fall into one of the following categories:

1) You need fresh eyes and/or feedback on your work.

You can only look at your own writing so many times before the words all start to run together and you miss the obvious.

The good news is you don’t necessarily need the highest-end mentor money can buy… you could reach out to a peer, colleague, or even someone who’s just starting out and ask for help with this. Anyone who knows what you’re trying to achieve and understands the mechanics/basics of good copy can help you with this… and sometimes they’ll even help you for free!

2) You need guidance and/or coaching and are looking to level up.

There comes a point where you realize you don’t know what you don’t know… and without outside perspective, you’re going to stay stuck where you are. In cases like this, you’ll need someone with more experience to show you the best way forward.

These aren’t all pay-to-play relationships – in fact, my first copy mentor was my boss/copy chief when I took a job in-house as a copywriter. It just so happened he was VERY good, and knew how to get me out of my own way.

A “copy cub” I work with (and have for the past year or so) is someone who keeps showing up and delivering value for me – she’s helping me write my book and holding me accountable to delivering something up to my high standards. She doesn’t pay me to coach her – she works in trade with me.

And of course, there is the pay-to-play… which is often the simplest and easiest way to get help fast. The key thing to remember here is that successful people are often busy people – and offering free help to everyone who asks means they can’t actually do the work they’re paid to do.

These successful folks have to guard their time carefully – and often the difference between someone who argues with your advice (or shows up for one session and then flakes out) and someone who has what it takes to excel? Willingness to put your money where your mouth is.

Respect for a busy person’s time and the value they’re adding to your life. Remember: you’re not paying them for a haircut… some one-and-done exchange. You’re paying them for a skill you can use to make money for the rest of your life. Some might even call that… INVESTING.

A note on paid mentorship – you want to make sure this is someone doing what you want to do SUCCESSFULLY before you pay for mentorship with them. A lot of folks sell the sizzle but have no idea what the steak even tastes like.

3) You need to learn or master a new skill.

If you’re interested in adding a new skillset to your offering, you’ve typically got two options – a) do a bunch of unpaid practice on your own time, b) sell it to someone and fumble your way through.

There IS an option c – and that is to invest in specialty coaching for whatever skill you’re trying to learn.

This strategy had never actually occurred to me (if it had, I’d have probably gone a lot farther a lot faster). I heard about it from a particularly brilliant copywriter I know, who would sell something he didn’t yet know how to do, like a video sales letter (VSL). Then he’d go find a VSL master to help him write this first one, and pay that person the bulk of the fee in order to persuade them to teach him their process.

After the project was done, he knew he would have the knowledge and skills to be able to confidently sell and complete a VSL on his own (not to mention someone he could pay a fee to in exchange for coaching and feedback – someone he already had a relationship with and could actually get on the phone).


My PERSONAL experience with being mentored has been a combination of all three of the above.

When I first started out and was largely independent (without the resources and network I currently have), #1 was my biggest value. I had to swallow the pride/ego and put my best (at the time) work out there, knowing it would be shredded by peers.

This process taught me a few things – namely, not to be afraid of feedback, and that I don’t have to take every bit of advice just because it’s offered. It taught me to trust my own instincts and fight for something I felt strongly about.

When I got stuck with my first foray into freelancing, I went in-house and had more of a #2 mentor.

I learned a LOT by taking this route. My first creative director was very formulaic and I outgrew the role fairly quickly, and sought a role that was more challenging. My second creative director and the copy chief he brought on were AMAZING.

I not only learned a metric crap-ton about retail copywriting, but also got amazing career and life advice, as well as earning the right to try my “crazy” direct response stuff in their more Madison Avenue-style advertising.

That freedom to try things and fail taught me a ton, and generated a lot of the multimillion-dollar sales results I currently hang my hat on. I was eventually promoted to senior copywriter and trained new hires and supervised our intern, and filled in for the copy chief when he was out.

When I got burned out on that role (2+ hours of daily commute, 10-12 hour days, toxic work environment outside my core creative team), I knew I needed to try freelancing again but had no idea where to turn because I was so overwhelmed.

Enter the #3 mentor, when I hired Kevin Rogers to teach me what he knows about freelancing. By that point I didn’t need copy coaching so much as I needed business coaching – still, that’s the point of coaching – finding someone who knows how to do the thing you want to learn to do, and getting them to stop what they’re doing and focus on helping you learn it too.



So have you ever been mentored (or been a mentor)? How did it go for you?



If you’re an aspiring freelancer who’s working up the courage to leave the day job… good news! I’m sharing all the things I WISH I’d known before making the leap so that hopefully your journey goes a little more smoothly than mine.

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