If you had told me ten years ago that I would be in the longest-running position in the history of my career, I wouldn’t have believed you. Back then, I was unhappy for various reasons, and while I had started to think about what I really wanted from my work life, I had yet to take some of the big steps to get there. I won’t go into the gory details of where I was or the situations that weren’t working for me. Suffice it to say that there was a lot that wasn’t working, and I didn’t know how to fix it… but I had some ideas.

If you’re sitting in a spot, like I was then, perhaps feeling a bit despairing and lost despite what many might consider your own success, this post is for you. It’s been written as a love letter, from the woman that I am today to the woman that I was then… Whether today you’re solving problems like a champion, just putting one foot in front of the other, or sitting on the couch thinking that you may want to get up – it’s all part of the journey.

Give yourself permission to name the things that you really want

Once, a former mentor (Lin, a founder of CU Training, now retired) literally gave me permission to take notes with coloured markers. The notes included cartoons of key points. I love to draw. It’s a great memory aid, but it’s something that I saw as being “unprofessional” and had trained myself out of…

This conversation got me thinking – what else hadn’t I given myself permission to write (or draw)? Were there things that I wasn’t giving words to?

Of course, there were.

In fact, there were a whole lot of things that I had been afraid, for one reason or another, to think too deeply about, let alone describe. So many of these things related to what I really wanted from life.

Write it down

This led to a trip to a shop in Victoria, BC, where I bought a beautiful notebook that I didn’t write anything in for a while. It would become the place where I wrote down what I wanted in life. This is the page from that book for “work.”

When I put pen to paper in this book, the rules are simple. I don’t beat myself up about what’s not working in my current state. I have a good think about what I really want, and I write it down. Whether it seems improbable or downright impossible, I write it down.

Looking back at this page, written over a year before my company, Outlier Compliance Group was a conscious thought, I can see its beginnings here.

Keep writing

I look back at and add to the old pages, building on the ideas there. It makes me smile to see where I’ve grown into myself and accomplished things that I thought impossible. I add new pages to the book.

It’s easier now to give myself permission to write than it was at first, but it’s still not easy! That’s okay. I think that’s part of how I know that I’m still growing and pushing myself.

Be open to opportunity

In the last decade, I’ve worked with amazing companies and entrepreneurs. I’ve consulted governments and NGOs. I’ve taught classes and presented at conferences around the world. I’ve made the type of career decisions and personal investments that have set me up to be secure in a way that I would have found unfathomable. Some of the people that I admire most in the world have become mentors and friends.

Sometimes, I think about where I was at various points in my life: living in poverty, in the foster care system, in very unhealthy work environments, and I wish that I could reach back into the past and let that version of me see the me that I am today… to let that version of me know that all of the hard work that I was doing would prepare me for opportunities that I wouldn’t have dared to dream of then.

The best part is that, eventually, success can become a virtuous cycle. The more opportunity I seize, the more seems to flow my way, and the more I am prepared to tackle… and the more that I am able to help others to help themselves along the way!

Take enough risk to get knocked down

This is not to say that it’s easy to seize opportunities, or that I don’t get knocked down from time to time. I do, and it’s not fun!

When something knocks me down, I try to remember that this is the price of “stepping into the ring.” Sometimes, I’ll get knocked down.

This is part of the risk-return curve; there’s no success without risk.

Get back up and do it again

Once, an interviewer presented me with a big list of leadership characteristics and asked me what the most important was to me. After reading the list, I asked if I could add another word to the list. That word is relentlessness, and I stand by it.

This is not to say that I keep doing the same thing over and over and expecting a different result, but rather that I learn, adjust tactics and pursue my goals with ardour.

If you can’t find it, build it

I think that everyone close to me had a sense that I would do something entrepreneurial long before I did. I was always looking for novel ways to solve problems, no matter the environment that I was in. This has become the number one question that I ask entrepreneurs that come to me for advice – what problem are you solving?

It’s important from a business perspective, as well as from a personal satisfaction perspective. When we understand what we’re doing and why, we all tend to be more motivated and focused.

Find your tribe

I am grateful every day for the incredible people in my life. I grew up feeling like an outsider, and I had to a large extent, accepted that this is the way I would always feel (and I was ok with that). It takes me by surprise sometimes to realize that I don’t feel that way anymore. I spend most of my waking hours solving problems and socializing with people that I love, respect and admire. Even when we’re dealing with difficult or stressful situations, I am still grateful for my friends, colleagues and clients every day.

The caveat here is that there are only 24 hours in a day. Each hour that you spend with the wrong folks is a missed opportunity to spend time with the right folks. Choose wisely!

Forgive yourself

This is something that I am still learning, and maybe I will be forever… When I make mistakes, I take it hard. I can hold a grudge for a very long time, and while I think that’s healthy in some cases, I shouldn’t be holding a grudge against myself. Making mistakes is part of learning and growing, and I need to be honest, forgive myself and get to learning rather than dwelling.

The idea that there are only 24 hours in a day is important here too. Time spent beating oneself up is not time well spent.