Five Lessons From Five Years Of Coaching

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Before we jump in: This article was originally shared with my email community in November 2019. I'm sharing it with you on the blog today in the hope that it may be of some encouragement and insight to you in your creative journey right now, and also give you a little sneak peak of what you can expect from Weekly Letters too. If you'd like to receive letters like this one straight to your inbox every Sunday, you can sign up below. You'll also have access to all of my Mini Books too!


In January it will be five years since I started my creative coaching business and I am so glad that I ignored the voice in my head telling me that I had no right to dream of doing this work as I am oh so grateful every single day that I get to call this my job.

I have been forever changed by this work, by the privilege of walking with my clients in their journey and bearing witness to their courage, their creativity, and their stories too.

Just this past year I’ve seen my clients do some incredible things. Get the book deal of their dreams, leave unfulfilling day jobs and do work that actually lights them up, stabilise their income so that they can find more ease and flow in their business, the list could go on and on.

But so much more than all of that, I’ve seen my clients make some incredible internal shifts too. I’ve seen them redefine what success actually means to them and find so much freedom in the process, be brave enough to show up for the work and dreams that truly matter to them, and come back home to their creativity too.

I have learned so much from doing this work in the world and I want to share five of the biggest lessons with you today, with the hope that they can encourage you in your own journey too.

It’s impossible to move forward if you’re trying to control the outcome

Business is, at the very heart of it, an experiment. There are no guarantees, no blueprints to follow, no roadmaps that don’t include some risks and some unknowns. Nothing gets in the way more of forward momentum than trying to control the outcome of your actions, as you’ll either struggle to find the courage to take the first step or you’ll quit at the first sign of a hurdle.

And I’m not saying this is easy, to wander into the unknown and trust that you’ll handle whatever comes your way, and I’m a big believer in taking that leap with as much intention and purpose as you can, but at some point each and every one of us has to surrender a little to the unknown. But here’s the thing: on the other side is usually something so much more than you ever even dreamed was possible, you’ve just got to find the courage to get in the arena and figure it out as you go.

Inaction is almost always the enemy

Almost always the best solution to my clients feeling stuck is to find their way out by moving through it. They’re worried they don’t have anything worthwhile to say on their blog? Start writing anyway. They’re worried they don’t know how to build a beautiful website for their brand? Get stuck into Squarespace anyway. They’re afraid to create this awesome new offering they're excited about in case no one cares? Dive in anyway. They’re afraid to write their book proposal in case no agent wants it? Start drafting it anyway.

I’m always reminding my clients that the answers and insight we crave can only be found in the doing, that we figure it out by getting stuck in and learning from the journey. Sometimes what they need most is just a clear plan of action to get them moving forward, and a reminder that they are oh so capable of taking this next step too.

But there’s also a season for getting ready to show up too

Action doesn’t always have to look like forward momentum, sometimes it’s a little quieter than that. I’ve seen many of my clients needing seasons to rest, heal, recalibrate, and refocus before they’re ready to take the next leap in their work. Choosing to do inner work instead of focusing on external goals doesn’t mean that you’re wasting time or standing on the sidelines, usually this work is the foundation of everything that comes next. Sometimes we need more clarity before the next step, other times we need to recharge from a busy season or process and heal from a challenging one, and that work is just as meaningful as ticking off those big action steps on our to-do list.

Redefining success is the foundation of a meaningful career and life

I see my clients crack wide open when they get to the heart of what kind of life and career they truly want to build for themselves, when they move past all of the external expectations that may have fuelled them so far and listen to themselves instead. And this isn’t easy work, it takes a whole lot of courage to leave behind a path that makes sense to everyone else so that you can choose the very best one for yourself instead. It takes work to strip back all of those layers and discover what is actually true for you, but there’s so much freedom to be found in this process.

Because when we redefine what success actually looks like for us and opt-out of everyone else’s narrative, we stop striving and we start truly living instead.

Discomfort is part of the process

Something I talk about a lot with my clients is expanding our capacity for discomfort, as so much of this journey demands that of us. Because it’s uncomfortable to ask ourselves hard questions, to face our hopes, goals, dreams, and fears head on. It’s uncomfortable to take up space, risk rejection, and get back up again every time we fall.

And the most uncomfortable part of all? Knowing that nobody else can do your business or your life for you (I even wrote a whole mini book about this!) Because the most important work I do with my clients is empowering them to know deep down in their soul that they are wildly capable of doing the work they want to do in the world. I’m here to help them listen to themselves, to offer up ideas and perspectives, to guide them when they get lost, but by the time we finish working together our goal is to leave them feeling oh so ready to steer the ship that is their business and their life. The journey to get there isn’t always comfortable, but it is always worth it to make it to the other side.

And the biggest lesson I’ve learned? We are all so much more capable than we think we are. I’ve seen my clients build beautiful lives and businesses for themselves and their first step is actually believing that they are worthy of that.

So wherever you are in your journey right now I hope that you know how worthy you are too, of living a life that is meaningful and joyful to you.

As always, I’m rooting for you!


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Jen Carrington