Ten Bold Moves I’ve Made in Business

Caroline Leon
9 min readFeb 9, 2021
Photo by Andrea Davis via unsplash.

“It takes courage to grow up and become who you really are.”
~ E.E. Cummings

In this article I share with you 10 bold moves I’ve made over the past 10 years in business, each of which I believe have contributed to the success I am enjoying today. All too often, when we’re in the throes of trying to get a business off the ground we forget the importance of being bold. I share these with you for inspiration.

1. Started a blog (2011)

Someone asked me recently if I thought they should start a blog and I nearly leapt out of my seat to say yes! I discovered the online world of blogging back in 2010 and after a year of devouring other people’s content, I decided to start my own. It is not an exaggeration to say that creating my first blog, Life is Limitless changed my life completely. The accountability that came from sharing my goals online and with my growing audience, motivated me to do things I might never have done had no one been “watching”.

The other, fairly significant, thing that happened was that I built an audience. By regularly publishing blog posts for years before I ever sold to people, I built a loyal and fairly sizeable following. Before I even knew what it meant to practice generosity in business, I was sharing my best content with people and asking for nothing in return. When I finally launched my business in 2014, it was pretty easy for me to create paying clients from my existing audience.

2. Made a huge leap of faith (2012)

In early 2012 I quit my lucrative career in program management, sold everything I owned, bought a one-way ticket to Thailand and planned to build a coaching business while travelling the world. Things didn’t quite go as planned initially. For a start I never got all the way around the world because I fell head over heels in love with Thailand where I embarked on a journey within, which included doing a lot of healing and personal growth work. This in turn led me to finding the love of my life, my life partner and now father to my two boys.

Once I had settled into my new relationship, I set about the business of building a business and even though it took a while to get there, the journey from that initial leap into the unknown to starting my own business was life-changing. I had to walk away from everything I knew and had to create the space for something new to emerge.

3. Hired a coach (2014)

Before I share more about this, I do want to say that I am not one of those coaches who says that in order to be successful, you must hire a coach. There are many business owners who have succeeded without investing heavily in business coaching.

However, I can’t deny that the work I did do with my coach definitely helped me to achieve success faster than I might have done alone. He also helped me to build my business from the ground up on a foundation of service and much of what I learned from him, I’m still teaching my clients to this day. I feel very fortunate to have had his guidance so early on in my business journey because what he taught me about authenticity and being of service, I now realise is so very rare in the online business world.

Coaching isn’t for everyone though. Personally I thrive on accountability. If I’ve told someone (such as my coach or you my subscribers!) that I am going to do something then I’ll do everything in my power to get the thing done. So you can imagine how powerful it was to have a coach who would set me bold challenges on the regular.

4. Accepted a crazy outreach challenge (2014)

One such bold challenge that my old coach set me right at the outset of our work together was to reach out to 50 people in 7 days. When he first said it, I thought he was crazy and tried to argue that I didn’t even know 50 people. One quick look at my Facebook profile put that argument to rest and I was left with little choice but to accept his challenge and go for it. I can’t begin to tell you the magic that challenge created in both my life and business.

My current, and totally amazing, personal mastermind partner, Eli Trier, was just one of the people I reached out to as part of that challenge over 6 years ago and we’ve been collaborating and hanging out online ever since.

Once I saw the magic of outreach, my business life was forever changed, despite being a hardcore introvert, practicing authentic outreach is not just how I keep my business network activated and alive but it’s also a true source of fulfilment for me in my work. Deepening relationships is one my favourite things to do in life and business and it just so happens to lead to more people buying from me too. If this sounds like a challenge you’d like to take on, feel free to message me for instructions.

5. Set myself a crazy coaching challenge (2015)

Riding on the high of the outreach challenge I completed the year before, and looking for the next bold move I could make in my business, I decided to set myself the challenge of offering 77 Complimentary Coaching sessions to my people. This was a huge undertaking and in the end nearly 100 people applied to have free sessions with me. And we’re not talking taster sessions here, we’re talking deep dive, 90 minute, powerful coaching sessions. I met SO many new and amazing people and enrolled a heap of new clients as a result. If you want to see what that offer looked like you can check out the page I created for it on my old website here.

Whilst there were times during this challenge that I felt completely overwhelmed and exhausted because there were many days I had up to 5 sessions in a day, doing these calls led to exponential growth in my business and expanded my business network 10-fold.

6. I started a new business (2017)

Then after a few years of business growth, a move back to Europe and a (shock) decision to start a family (I never thought I would have children), I became a mama in March 2017. Something about being pregnant made me face the fact that I wasn’t enjoying life coaching as I had hoped I would and I decided that the successful business I’d built no longer served me and decided to pivot into business coaching.

That meant walking away from a loyal and engaged following that I had been growing for 6 years! Including a list of nearly 1000 subscribers, a facebook page with 1.3K likes, an engaged Facebook group of several hundred people plus a source of regular income.

So, as you do, during my maternity leave, I built 2 new websites, launched a new business and a business academy and promptly looked on in horror as my income plummeted. Despite this, it was without doubt one of the best decisions I’ve ever made and once I started to get traction and made more bold moves, I watched (with some relief) my income start to grow once again.

7. Reached out to my business peers (2018)

After what felt like a year in limbo working hard to get my new business off the ground, I knew in my heart that there was a more meaningful way to do business, but I wasn’t finding as much evidence of it as I would have liked. This changed completely when I started to discover people like George Kao (authentic business coach), Alice Karolina (Founder of the ethical move), Tad Hargrave (Marketing for Hippies) and Mark Silver (Heart of Business). Here were four successful business owners doing business with authenticity and integrity and I didn’t hesitate to reach out to each one.

Over the course of that year and beyond I devoured their content, took their courses, shared their important work with my audience and even got got coached by some of them. Not having a clue that Just a few years later, I’d be sat alongside several of them on a discussion panel about Ethical Marketing at the world’s largest ever online conference. I’m also now a member of the the ethical move team, helping to shape the future of this important movement and getting regular client referrals from George!

Imposter syndrome could totally have got in the way of me making these important connections but instead of treating these people like heroes (even though of course they are to me!), I treated them as trusted colleagues and I showed up to our interactions, confident that I had something to offer. Don’t get me wrong, doing this required courage but I was determined not to let my fears keep me playing small.

8. Studied my craft hard (2010 — present day)

Since I first made the decision to walk away from an established career in program management to become a coach, I have never stopped learning. I knew early on that what I wanted to achieve was mastery in my skills as a coach and since letting go of my life coaching, I’ve committed myself fully to mastering what it takes to grow a business with integrity. What helps is that I have a growth mindset, so rather than see myself as limited in what I can do, I choose to believe that anything is possible if I put my mind to it. I then go put my mind to it and the impossible happens.

9. Set myself a crazy content challenge (2019)

In April 2019, aware that I had already fallen behind on my commitment to publish a weekly blog post, knowing the importance of content creation, I decided to set myself the challenge to write 30 blog posts in 30 days. This might not have been so crazy if I wrote short (Seth Godin style) posts but given that I tend to write around 1000 words per post, this was challenging to say the least.

It was an intense month, let me tell you! Aside from client calls and blog post writing I did little else, but the rewards were incredible. I deepened my own habit of writing, I created a huge raft of new content for my website and my audience and I learned a lot. To read exactly what I learned and to get links to all 30 posts, head here. One of these posts even brought me new clients! I have no doubt that it was this challenge that improved my SEO and web traffic stats. These days it’s not uncommon for new clients to find me on Google, something else I never could have imagined (given just how many business coaches there out there!) but my commitment to content creation continues to serve me well.

10. I spoke in front of the largest audience of my career (2020)

In many ways, this feels like a culmination of all of the above. First of all I was recommended by George to the organisers and when they approached me of course I said hell yes! Even though I didn’t make the initial move, this still feels like a bold move for me in a couple of ways. First of all, I took the invitation seriously, seeing instantly what an incredible opportunity it was offering me to spread my message.

Also rather than just doing what was asked of me, I was proactive when liaising with the organisers of the conference, and asked if there were other parts of the conference I might have a role in or be needed for, which is when I was invited to be on a discussion panel alongside some of my own mentors. I’m not ashamed to share that I was terrified, I even contemplated telling them I couldn’t make the discussion panel part as it was very late in the evening in my timezone. But the bold part of me won the inner battle and I said, yes of course I’d love to be on the panel!

The other bold move on my part was showing up as powerfully as I could. In my earlier years of business it wasn’t uncommon for me to sabotage my own success by leaving things to the last minute or not responding quickly enough to invitations. I did not do that here! I worked my ass off to create the best presentation I could and I practiced it several times before the day. The feedback and response I’ve had from that presentation has blown me away and I’m thankful that I chose to show up as powerfully as I could rather than succumb to self doubt.

And there you have it, 10 of my boldest moves in business over the last 10 years.

What thinking about these has shown me is the importance of making the decision to go beyond the confines of my comfort zone and, once past the border, going all in on my bold move.

And so I’m curious, what bold move will you make in your business today?

If you’d like to read more from me like this directly in your inbox, you can head here to subscribe to my Soulful Strategies Weekly.

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Caroline Leon

Business Coach helping conscious change makers to build and grow sustainable businesses, using strategies rooted in integrity. https://carolineleon.com