The Single Greatest Challenge You’ll Face as An Entrepreneur

by | Sep 3, 2018 | Podcast, Season 1

Today is a sad day for me and my family. It’s the one-year anniversary of losing our little dude, our Frenchie named Charleston. He was only seven and he had several seizures over a couple of days, and then we lost him to a brain tumor. The reason I am sharing this with you, is because I didn’t actually realize that today was the actual anniversary when I decided on this ‘letting go’ topic for Episode 9. The first time I discussed this topic was at a keynote speech in Portland, just weeks after this loss. You’ll see why this connection is important a bit later on, but I just wanted to take a moment to commemorate Charles. Our wee man… and all the animals in our lives who remind us to chase and be present for what really matters.

I am dedicated to helping entrepreneurs find freedom and fulfilment

By building brands instead of just businesses. What I do is a mashup of marketing consulting, brand development, strategy, problem solving and usually a little bit of magic.

The pursuit of freedom

Is something I take very seriously. It’s the reason many of us started our own business: to have time to spend with our families, to be our own boss… to have a ‘lifestyle business’ but man how quickly that becomes something that looks a lot less like freedom and a lot more like overtime, stress and like 24/7 commitment and worry!

When my clients come to me it’s almost always because they are a long, long ways from anything that feels like freedom or fulfilment. Almost always it’s burnout, overwhelm, confusion, or dissatisfaction that brings people to my door. When we begin our work, it’s usually in the aim of creating or building something. A brand, a website, a plan…

Most of my clients are standing at some sort of crossroads

My job is to help them navigate some sort of fairly radical change. A change that will ultimately get them closer to their version of freedom or fulfilment.

This process, is messy. Sometimes painful. It’s confronting. It’s raw.

The insight I want to share with you today is a glaring truth that has emerged from hundreds of these conversations…. and that is this:

No matter how much you want to convince yourself that it’s what you do, build, sell, create, trademark or perfect that will ensure the success of your brand, the ugly truth, is that it is in fact what you let go of that will define you.

It will not be what you have – but what you release – that will make or break you.

In my experience, our ability to let go, is the single greatest challenge we face as entrepreneurs.
And unfortunately, as I expect many of you already know, that letting go, almost always involves walking straight into an inferno of huge fear … Your resilience in the face of that fear and failure that defines your success.

I would like to take a moment to tell you a couple stories that I hope might inspire you…

The first is of a client who was very sure that the way she wanted to use our time together was to help her reach her first six-figure year. She was very fixated on this goal, although it was not based on incremental growth or performance – it was simply the version of success she wanted most at that time.

We began working together at the end of August, and she had 30k still to earn before the end of the year, with zero plans or prospects for achieving this goal. After a few sessions, and some discussions about realistic growth, product and pricing strategy, marketing channels and promotions that might give her some quick wins – she relaxed a bit and decided that maybe she was pushing really hard for a slightly superficial goal. She decided that actually instead of a frenetic push for revenue, our time might be better spent putting a more lasting, long-term plan in place, to ensure that the following year she’d easily hit that six-figure year.

I was happy to help her either way, but wouldn’t you know it, as soon as she let go and made the shift to allow herself the space and grace to do the deeper, slower work – she ended up hitting her six figure year– almost as if by accident. It wasn’t actually the goal she let go of, it was the all the negative self-talk, fear and criticism she had been dumping on herself for having NOT hit the goal yet, and what that must MEAN about her and her business. Almost the instant she moved into a more positive space, and let herself off the hook, everything began to flow towards her.

The next little story I’d like to share with you

Is about a multi-talented entrepreneur who came to me with a strong local business, but a desperate need to build her online business. She was happy with her in-person sales but wanted to increase her passive income products, build a stronger presence online, solidify her brand and invest in ‘stepping up’ her game – since she had DIY’d all of her marketing and branding when she launched and not really revisited it since. We set about working together one on one, defining her brand pillars, and brand statement – when it suddenly became clear that we had very different expectations about what it would mean to ‘refresh’ her brand… She was fully committed to keeping her logo and website the same– hoping that changing the words on the website would be enough to accomplish a ‘brand refresh’. On the other hand I was under the impression she was prepared to change it all in order to achieve her the ambitious goals we set together.

There was an awkward and tense couple weeks as I tried to help her as best as I could, within the confines of her comfort zone, until one day she decided she was ready for a new logo, but not a new website… Then not long after, she realized all the work and investment wasn’t really going to have the impact she desired if she didn’t just go all in. The issue for her wasn’t really about the investment, or the work – she was ready to give her all – it was a deep connection to the logo and website and copy she already had, her own ideas about how customers should be using it and perceiving it, and an incredible fear of the mental, emotional and time-related demands a project of this scope would require. It was just too much. So, gently, my team and I set out to help her get the best results we could within the restrictions of her fear, until again one day, she got in touch and confirmed that ‘OK, I’m ready’ – I am all in.

She let go of her doubts, walked straight into her fear, practiced letting go over and over again as she let a whole team of professionals help her refresh her logo, design, a new pricing structure and a new website – she wrestled with her own personal taste versus the sometimes conflicting advice of those experts – and literally forced herself through the transformation one painful step at a time.

About 4 months later when she finally had her new logo and launched her new website, not only did she experience relief and euphoria at having survived the fear and resistance she was battling previously, she also experienced an immediate doubling in sales of her passive income products, and was inundated with new opportunities for press, television, custom projects and more. Our work together was an outrageous success by all measures, and it was only possible because she found the fortitude to let go, one baby step at a time.

* * *

Now, as I mentioned, today is the anniversary of a different kind of loss for me personally. The sudden loss of a beloved dog. In the space of 3 short days he’d gone from what we thought was a perfectly healthy 7 yr. old dog, to, just, gone. We are still working on embracing the loss and change that came as a result of losing Charlie, and it seems fitting to mention it since we’re here having a conversation about letting go. Let’s be honest: It’s hard. It sucks. It’s unfair. It doesn’t get easier.

Losing a loved one, facing your fear, taking big risks, having no control about the big things in your life – you know what? When they’re happening to you, they can all feel exactly the same – equally destructive. Equally sickening.

But even in our most unexplainable, disastrous lows – even when we feel we have no control – we still have one choice. We can allow these losses to break us – or let them galvanize us into the people are meant to be. Serving those we’re meant to serve. Sharing messages we feel compelled to share. Connecting with people who need comfort we can provide.

Fighting for causes and building brands that really matter.

Three years ago, when I lost my beloved Great Dane Olivia, I was able to spend two solid weeks of quality time saying goodbye to her. I didn’t have to ask anyone’s permission to stop my life and lay by her side 24 hrs a day. It stirred up in me the cause that I want to fight for, and that is:

helping each of us take ownership back of our most precious resource: our time.

The loss of Olivia was the reason that I started my consulting business and became obsessed with helping other entrepreneurs find freedom and fulfilment… so they too could have the luxury of spending time with the people and animals that make their lives worth living. Not just when they’re sick, but every day, in all the small ways that matter most.

This anniversary of losing Charlie, although sad, is a powerful reminder to me of exactly why I do what I do. Although his death was sudden, because of my obsession with chasing freedom and fulfilment, his life was remarkable. We had the great fortune to travel together all over Europe – living for months at a time in Spain, France and Italy. He chased balls on world class beaches, laid in the sun spots on ancient terraces, dined in michelan star restaurants and he marked his territory in over 10 countries. Although accepting change like this is excruciating, losses make it impossible to ignore just how essential all of this fluffy ‘freedom and fulfilment’ chasing is. Just how critical it is that we don’t wait to find time to do the things that really matter.

Change isn’t always optional. It doesn’t often feel good, but it is always a chance to start fresh. It can be a great catalyst for finding out what our version of freedom looks like and a fantastic source of motivation to make it happen.

So, today, I’d like to leave you with a few thoughts and one challenge.

When it comes to letting go, there are 5 key spots I suggest you start looking for some baggage to ditch:

1. The first one is other people’s definitions of success or happiness. The sooner you can ditch other people’s expectations or judgements about what you want, need or ‘should do’ the faster you’ll feel free.

2. The second place to start the process of letting go, we touched on last week.. The question I’d pose to you is ‘how do you most want to spend your time’ – start to get very clear on the the ways you do and do not want to be spending your time, and begin the work of letting go of, delegating, or outsourcing everything you’re currently doing that doesn’t make the list.

3. The third thing (which is very tied with accomplishing #2), is the need for control. Yes, it’s easier said than done to pass things on to other people to do and possibly screw up, but this is an essential growth step on the path towards freedom that anyone who’s done it will say is one thing the wish they’d done sooner. Learn to let go of control.

4. The fourth key bit of baggage I’d work towards releasing, is any anger or fear-basd feelings you have around your competition. There IS ENOUGH TO GO AROUND and you’ll be a much happier, free’er person if you find a way to truly believe that and act accordingly. Be generous by default. Good things will come

5. The fifth and final one, and possibly the most important, is to ditch your excuses. One of my favorite quotes is:

“You cannot be committed to your bullshit and your growth, it’s one or the other” – Scott Stabile

When you feel or hear your BS excuses rising up, consciously work on letting them go – ditch the defensiveness and commit to your growth. You can’t have them both.

And lastly the challenge I’d like to leave you with today – for your action item list – is this:

Write down one thing you KNOW has been standing in your way – either because you’re afraid to try or fail, or you can’t let go. In this safe space– I’d like to challenge you to commit to moving past this thing.

I’d like you to write it down, and set a date by which you have a plan of action for moving past this one thing. It can be something big like transitioning out of a lease or a partnership, or something small like just simply letting go of a to-do list item that’s been lingering for months and just letting yourself off the hook for it.

Think of this as emotional decluttering challenge.

A personal invitation from me to you, to let go and make room for greatness.

Pop on over to our private facebook page, Magic Makers HQ and we can chat about some letting go strategies – and celebrate the things you manage to say goodbye to.

This is your first step towards your own unique brand of freedom and fulfilment… and all the rewards that come along with it.

That’s it for episode 9 of the Magic Maker podcast – welcome to the headquarters of entrepreneurs who want to do good, be real, find happy and build brands that matter.

We’re thrilled you’re here.

Of course, we would be so grateful if you would be willing to invest a few moments of your precious time by reviewing this podcast on iTunes, so we can reach more magic makers and help too, to change their lives, and the world.

We’ll see you next time

To create freedom and fulfillment in your business and life

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