How to mentor your damn self.


My most vivid memories of 2015 are marked by two events: 1) Cracking my first 6 figures, and 2) My frantic, almost desperate search for a mentor.

The first was a fluke. I got swept up in a high-level contract with a dazzling number of zeroes tied to it that went belly up fast. Those months of stomach-turning in-over-my-headedness pushed me juuust over the financial edge.

The second had been years in the making, and came to a head as I dragged my limp body through the final days of the aforementioned contract, grumbling “If I had a mentor, they could’ve warned me…

See, when I got my start at 22, I never imagined I’d be in business for so long without any real guidance.

I subconsciously assumed that if I could scrape by in the first year, live off ham sandwiches, and piece together whatever shreds of strategy I could glean from my clients and digital forebears, someone would come discover me and save me from the Wild West minefield of digital solopreneurship.

If I worked hard enough, surely I’d eventually dazzle some influencer so much they couldn’t help but crow “I’d LOVE mentor you”, and I’d spend the next several centuries basking in the glow of validation.

But 4 years had flown by in a blink… and I was still waiting.

Despite the headway I’d managed to make, and all those zeros in my “gross revenue” box on my tax forms, I still felt like a kid standing on another kid’s shoulders in an extra-long overcoat, trying to blend in with the grownups.

And now I had goals beyond mere survival; and they were gorgeous, gleaming, and heavy as marble. I wanted to create + launch a course. I wanted to write more, be more visible, and expand my reach. I wanted to get seen on the grand digital stage as a player, and not just another clone chanting in the choir line.

Surely, this was too big to do alone. I needed help. I needed a champion. I needed a mentor.

… And I’m ashamed to admit: I also didn’t want to pay them.

Not just because I didn’t have the money (good teachers do not come cheap). Because I wanted to be chosen. Anointed. Told I was worthy of the time and attention and guidance I needed to succeed the way I wanted to.

I had friends with dedicated mentors, and their stories made me twist in my desk chair with envy. I always pictured them across from each other at coffee shops and fancy dinners (on the mentor’s dime, obvs); one receiving wisdom and one dispensing it, the dispenser sharing tips to avoid common pitfalls while assuring the recipient lovingly, “I learn as much from you as you do from me.


So when 2015 rolled around, I decided to be more proactive.

That meant tackling my mentorlessness in much the same way the baby bird does in the P.D. Eastman book “Are You my Mother?”:

I began asking around. Shamelessly.

To clients I liked: “Are you my mentor?”

To respected colleagues: “Are you my mentor?”

To bloggers I followed: “Are you my mentor?”

Most said no. They didn’t have time.

Some said yes, and never followed through.

Others tried to sell me coaching packages I absolutely couldn’t afford (Including, almost hilariously, a $20,000 mastermind. Amazing for businesses at the right level, but a panic-inducing pitch for a 26 year old who’d hadn’t spent 5 figures on anything but rent.).

For better or worse: Unlike that little baby bird who finds its way to its mama’s nest, my mentor never materialized.

After months of knocking on doors, I was forced to accept that no one knight in shining digital presence was coming to rescue me. I was going to have to go it alone.

It made me desperately embarrassed and insecure for a time. Everyone else I knew seemed to have a mentor. Why didn’t anyone want me? Why wasn’t I good enough? Could no one see that I need a little god damn help over here?!

Weeks later, I relayed this lonesome saga to a painter friend who put down her brush and looked at me thoughtfully:

“Have you ever seen my early work?” she asked.

“Yes!” I said brightly — and I had. All gleaming, jeweled tones with a Klimt-gone-confetti feel, quite different from the more muted, almost gothic tones in her current work.

“I can’t paint like that anymore.”

I was startled. “Why?! What happened?”

“I started taking classes with a wonderful teacher. But unfortunately… that class trained all my original natural style and instincts out of me. It gave me rules and practices I wasn’t burdened with before. I don’t regret it necessarily, and I love my art, but I’ll never know where that first point of view could have taken me — and that’s a shame. It could’ve been beautiful.”

It could have been beautiful. That got to me.

I’d come this far alone on the steam of my natural style. I didn’t want to lose it. Maybe things could be beautiful for me, too.

As I chewed it over, it began to dawn on me: Deep down, I didn’t actuallywant a mentor. Not really.

What I did want was someone else to shoulder responsibility for my business. I wanted someone to tell me exactly which ideas were good and bad, which sales strategies to follow, what clients to work with, and what my brand was. I wanted someone who’d praise the beejezus out of me when I did well, and whose “bad advice” I could quietly blame when I didn’t.

And at the crux if it all was fear. I wanted someone in my corner because the idea of a business built 100% on my own decisions and ideas and instincts scared me half to death.

And yet… there I was. I had already survived this long — even thrived some days. Maybe I didn’t need to be rescued after all.

That’s when I decided I’d mentor my damn self — and I’d do it the same way I’d learned to do everything else: imperfectly but passionately, one wobbly step at a time.

And you know what?

did create and launch a course. I did write more, become more visible, and expand my reach. I did get seen on the grand digital stage as a player.

Now I’m proud to report I did it all on my own steam, and in my own way.

Did I have questions sometimes? Yep, and I knew who could answer them (more on this in a second). Was it scary? Some days.

But what it taught me was that it’s possible to learn to trust myself without needing outside affirmation and validation. That I can run with my ideas without waiting for 50 people to high-five me before I get started.

Don’t get me wrong: Mentorship works in a whole lot of ways. Some people thrive with it, and that’s a beautiful thing.

However, there comes a time when we have to sit ourselves down and find out if we really need help, or we’re actively looking to give a little (or a lot) of our power away; just because carrying the weight of our decisions everywhere freaks us out.

But not all burdens need to be put down. Not all paths need to be perfectly paved by someone else before us. Sometimes we just need to adjust our packs and continue the hike.

One of the questions I always ask my students or colleagues experiencing #FOMO (Fear Of Mentorless Oblivion) is the same question I asked myself:

Do you really need a mentor? Or do you just want to stop making your own decisions for a while?”

You may just be lonely, or isolated, or letting your self-doubt win. Address that first.

And when you have? Pursue a mentor if that’s right for you.

But if you’ve come pretty far on your own, may I recommend a different path: the one you’re already on.

Here’s how to get the help you need and mentor your damn self… without letting one person reshape what’s already working.

How to mentor your damn self:

Tip #1: Have 2–3 trusted allies you run ideas by AFTER you’ve fleshed them out.

No more than 2–3 people, and definitely not people outside of entrepreneurship or your industry.

Find people you know and like who will be honest, who you trust and respect, and who have the kind of success you want. Run ideas by them (with permission) if you get stuck and see what comes back.

Teach yourself how to accept some ideas and reject others that don’t vibe. Learn how to take and use criticism. This helps you figure out how to defend your own ideas, and create with conviction.

Hint: If you’re rejecting all advice that disagrees with you, that’s a sign your ‘use the criticism’ muscle is weak. Spend time bulking that sucker up without resorting to defensiveness or stonewalling. It will only serve you.

Then: STOP. Don’t ask your best friend, your significant other, or your mother in law outside of your industry. Ask your advisors ONLY, chew over their response, and get back to work.

Tip#2: Find teachers you respect and know deliver value, and be willing to pay them.

This is a big one. Good teachers give you good examples to emulate, and help you find different ways of seeing things.

The first investment I made in business development was Erika Lyremark’s Mark’d Mastery group business coaching membership for women. I’m still in there, and it’s been a game changer and a lifesaver for me more than once.

While the group environment isn’t quite the same as 1–1 mentorship, it works beautifully, because it forces me to prioritize actively getting the help I need. The group rate also makes it affordable.

When you’re ready for the next level? Go higher.

I just began work 1–1 with a legendary business development and brand strategist to design the next phase of my business, which is entire galaxies larger than my current model. But the ideas are all mine — she’s just helping me shape them.

It works like magic.

Tip #3: Practice finishing what you start.

Being able to bring ideas from concept to fruition on your own steam is one of the greatest skills you will ever learn. This is also how you discover what good ideas feel like in your body, and find out exactly what you’re capable of (and what’s “too much”).

One of the biggest reasons I hear from people about why they need mentors is that they “never finish what they start”.

Newsflash: Only you can fix that. You can get guidance and support, but that’s as far as it can go. All the accountability buddies in the world can’t actually make your fingers and mind move to get things done. That’s on you.

Also: Why wait for a mentor? Look up productivity practices, and experiment ’til you find what works for you. It takes some time, but it’s simpler than you think.

Tip #4: Develop a practice of radical creative self-reliance. Ask forfeedback when you need it, but never ideas.

The only person you should pose the question “What should I blog about this week?” to is yourself.

Ask your teachers “Do you think this blog post illustrates ____ properly?” if you need to, but never make them do the heavy lifting for you.

As a writing teacher myself now, the most frustrating student response in the world is “I don’t know what to say.”

Yes you do. You’re just hiding behind a mental block right now for one reason or another because you’re afraid of failure, or of saying what you really think, etc.

You’re not sure what to say? Start asking yourself some questions. Start writing something, anything and see what comes out. But the only person who can save you from that blank page is… you.

Tip #5: Join communities in your industry.

For example, my favorite digital hangout is The Copywriter Club on Facebook. It’s teeming with writers from all over the world at every level and in every discipline, and the amount I’ve learned just by asking questions or reading threads is head and shoulders over the single perspective a mentor could have ever offered me.

(I’ve also been on their podcast. Holla!)

I’m also part of Margo Aaron’s amazing virtual co working space The Arena. Getting insight from people outside my immediate industry has been invaluable.

Just remember to take community responses with a grain of salt, too. If something sounds to good to be true, remember that person may be trying to sell you something.

Tip #6: Learn how to make mistakes and make ’em fast.

You can’t be scared to fail or fall over — it’s inevitable. What matters is your ability to pick yourself back up and keep going.

Resilience is a learned skill. Everyone you know who bounces back in a snap has a wealth of experience with any number of lurid challenges, flops, and roadbocks. But their history only motivates them.

Mistakes do not signal the end of your business. A lack of motion does.

Train yourself to roll with the punches. Don’t get too down on yourself, learn your lessons, and keep going. I promise: It’s easier than you think.

Sure, the road of self-mentorship isn’t for everyone. But if you’ve come this far on your own? You’re probably mentoring yourself already.

Now all you have to do is keep going.

Learning to trust yourself, and count on yourself above all, is one of the most precious skills you can have as an entrepreneur.

So don’t be so quick to turn to someone else for the answers. Consider sticking it out, swallowing your panic, and finding your own way out of the woods.

Let yourself follow the road to where your own beauty leads.

Don’t wait to be chosen. Choose yourself.

Photo by Arisa Chattasa on Unsplash

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2 thoughts on “How to mentor your damn self.

  1. Loving this post! I’m definitely guilty of waiting for someone to come along and show me THE way, the guaranteed path to success, so this was just what I needed. Being self-reliant and ready to make mistakes is scary, but I know that’s exactly what I need to do. Thank you!

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