During the thick of the recession, a writer, who I have looked up to since I was a child, emailed me, asking for help. She’s a “name” writer, someone whose work is synonymous with her name. I have known her for many years through friends of the family.

Knowing that I had experience in journalism, she asked me if I could put the word out to my contacts to pitch them her column.

I truly wanted to help her but had no idea how. I didn’t have the contacts she assumed I had, and didn’t feel comfortable cold calling, since I’m terrible at pitching myself (and still am), much less someone else. The whole scenario made me incredibly uncomfortable. I didn’t want to believe that this writer – a hero in my eyes – was so hard up she had to resort to asking me – lowly ol’ me, of all people – for help.

When I wrote back telling her this, she responded in complete defeat, saying she’d probably have to look for a job in customer service, seemingly every (antisocial, reclusive) writer’s worst nightmare.

I felt terrible, but I also felt defeated. I thought this woman, who I admired with my whole heart, was invincible. She had proved to me that she wasn’t.

I’ve been thinking about this incident recently because I’ve had several people tell me that they look up to me. While I assume my natural reaction should be to be flattered, it instinctually makes me anxious.

I am quicker to list my shortcomings than I am my accomplishments. I wonder what these people who look up to me would think if my career started slumping, or if I stopped being a writer (my nightmare). While it’s an amazing feeling to be admired for my work, the pressure of maintaining whatever it is they see in me is all too exhausting.

I met up with my very special friend Louise, to gain some insight. Despite being six years younger than me, she’s one of the wisest people I know. When she was 15, her band Lillix was signed on the spot to Maverick, Madonna’s label at the time.  Unlike many musicians, she got to live the pay off of her hard work. By the time she was 16, she was fully living the dream – touring the world, being profiled in magazines, flying first class, playing to thousands of people.

These days, Louise still makes a living with her music, though not on the same level as before. And while haters might be quick to assume she’s resentful or unhappy, they are totally wrong. She’s more content now than she ever has been, thanks to her unique experience and the perspective it’s brought to her life. And that is why I look up to her.

I told her about my discomfort with being looked up to and she assured me that I was being a dumb-dumb head.

“No one successful has gotten to where they are without going through the downs,” she said. “And it never ends. You have to be okay with that.”

The writer who contacted me during the recession ended up selling her column to several newspapers across the continent. Since then, work has never slowed down for her. Although she obviously felt a moment of desperation when she emailed me for help, overall, she never really had to feel that way. I had secretly known that all along. It just made me unsettled that she hadn’t.

Before I left my pow wow session with Louise, she told me that in her eyes I would always be a successful, established writer. And for once, I didn’t instinctually feel anxious. Instead, I felt good.

This one is dedicated to Ms. Jill Borra and Mr. Kevin Siu of the Globe and Mail. I’ll be contacting you soon.

I was talking to my friend in New York last week about her husband whose career is on the verge of exploding. He’s the most driven, confident, and self-assured person I’ve ever met in my life. Ever. Ever. Ever.

Lately, he’s been working harder than almost anyone I know and apparently, it’s getting to him.

“It’s like he wants a gold star on his forehead,” his wife told me. “I think I should do that. I think I should go out and buy a roll of gold stars from Sandylion and stick them on his face, one by one until he looks like David Bowie.”

In short, this guy needs confirmation about everything.  Everything. Everything. Everything.

I totally get it.

Recently, a few of my girly girls and I have started playing a very healthy game where we’ll sit around on a bed and say at least one nice thing about each other before the end of our hang out session. (Reminiscent of this.)

You want to know why? Because most of the time, we’re all in our heads, telling ourselves we’re not good enough, our work isn’t good enough and everything we do isn’t good enough.

So it’s nice to have friends who can play along with this game where you not so gently stroke each other’s egos. You don’t even know how good it feels until you try it.

It’s a feeling you can get used to it.

This week I used Facebook to ask my followers to help me describe I’m a Good Story, partially for work reasons, but mostly for ego-stroking reasons. Here’s a few things people said:

“Elianna Lev doesn’t want to make you uncomfortable, but she does, usually by writing about the things that make her uncomfortable, of which there are very, very many.” – Sarah Steinberg, my editor at enRoute and my former editor at Vice

“Honest, heart-felt and at times poignant, I’m a Good Story tells of the journey to find truth, inspiration and personal insight amidst the beauty and schlock of post-postmodern life and relationships.” – Hilary Henegar, my editor at Granville magazine

“Personal, without sentiment, honest without being precious, always leaving the reader with a lesson or piece of useful insight” – Louise Burns, professional musician, formerly of the band Lillix

That felt great until my ex-boyfriend, professional improviser and certified jerkface Taz Van Rassel chimed in:

“Remember that girl in high school who told you every detail of her life regardless of whether you asked or not? That’s what I’m a Good Story is like, but less gothy.”

I’m in an interesting place in my career where I’m about to start taking more chances. I have to or else I won’t get where I want to be. It’s terrifying and thrilling and, really, all I can think about. I’m one of those driven types who won’t settle until they achieve what they want.  And what I want are big, big things.

I met with five of my mentors this week to ask for guidance as I enter this critical point in my life. Here’s the wise words I took away from each of them.

1)   You’re doing the right thing.
2)   Don’t think. Do.
3)   The world needs people who do what you do.
4)   You are good at what you do.
5)   When you write a story, write more than one side to it.

It helped a lot.

There are a lot of people like me. And many of us seem to be in the same place right now, all waiting for our big moment and working our asses off until it happens.

If I had one word to describe this weird place we’re in, I wouldn’t use the word “fulfilling.” Instead, I’d use ‘stressful.’ I’d even use all caps: ‘STRESSFUL.’

(As I’m writing this, I’m toggling between five different files and my web browser, working on two different contracts, one huge pitch and on the phone ordering some overpriced iPhone text plan for the US, as I’m taking a trip to LA with my writing partner later this week. STRESSFUL.)

We driven types work hard and often we’re rewarded. But equally as often, the reward doesn’t feel quite as good as we’d expect it to feel, considering the amount of energy (STRESSFUL energy) that was put in.

But whose fault is that?

I’ll think about that when I have a moment. But for now, I have way too much work to do.

——

My mentors, listed in order of how their advice appeared:

1. Terri Theodore, reporter and broadcaster extraordinaire for the Canadian Press

2. Marsha Lederman, Western arts correspondent for the Globe and Mail

3. Catherine Winckler, partner and creative director of Switch United

4. Steve Pratt, director of CBC Radio 3

5. My dad.