Hi there [👋].  My name is Cherie [she/her], and I can hand-on-heart say that one of the very best things I’ve learned from owning [and scaling] The Digital Picnic over the last x8 years [and counting] has been the plethora of leadership lessons I’ve learned along the way.

I often say to my business coach, people would pay tens of thousands of dollars to get the kind of personal [and professional] development I get to receive just for having made the decision 8’ish years ago to explore business ownership.

Christ, Australia’s former Prime Minister [#ScottyFromMarketing] dropped 1mil per annum on empathy coaching alone … when I could’a told him, “you don’t need an empathy consultant … just own a small business for x8 years, and employ a team of humans you really care about”.

Free empathy consulting.  

Like, 24/7.

I feel like the luckiest woman knowing that I’m going to my one-day grave having clocked up a lifetime of relentless personal and professional development, courtesy of having landed in the position of organisational leader within this here small [but growing] business.

… here’s some of the lessons I’ve learnt from some of the hard[er] leadership lessons.


Being able to constructively receive feedback is like breaking free from a prison your own ego has locked you up in


So, like, enjoy your Michael Schofield ‘Prison Break’ escape.

I can whole-heartedly say the only reason why you think feedback is scary, is because your ego is tricking you into thinking feedback is something to be feared: it’s not.

Actually, these days? I fear not receiving feedback.  Because I’ve experienced life as an organisational leader who’s not receiving feedback [at all], and it doesn’t feel great.  At all.  Actually, it feels unsafe.  

It’ll forever be an unsettling feeling for me to sit in either a) artificial harmony, or b) no feedback at all: good, or constructive.  And if you’re the kind of leader who can’t handle constructive feedback? … brace yourself for artificial harmony, or no feedback at all.

It is a special kind of hell, because you know folx are unhappy … but they’re not raising it, so it’s this weird, quiet resentment [and it’s just toxic].

The antidote? Feedback.  And it’s on you to model being able to receive feedback, and to well and truly walk the walk in this space.  And when you do that? You encourage feedback culture more broadly, and the ripple effects of that will be a workplace that’s the radical candour to another’s artificial harmony.

TDP used to be artificially harmonious, and I can hand on heart say that it was some of the most miserable days I’ve ever had in business … and as an organisational leader within this business. #NeverAgain


Your commitment to people-please will destroy you [and your business]


This one is an ongoing work in progress for me [cheers, childhood trauma. #lol].  I am a prolific people pleaser, and of all of the responses to distress [i.e fight, flight, freeze and fawn] … I’m your 10/10 fawn responder.

If you need a visual to help you understand what a fawn response is? … it’s a baby deer > in a paddock > under threat from someone/something, and their response is to lay on their backs > feet in the air, while that “threat” comes along and takes them out.

Fawn response, yea? … and it’s horrible [again, cheers childhood trauma.  Or more specifically? Debbie.  My God-awful bio Mum].

What I’ve learnt about people-please, professionally speaking? Well, it’s actually something I have even been able to quantify on paper [well, spreadsheet, more specifically] … and that’s that the very worst this business has ever performed [think consecutive losses: month on month, and really large ones] has been when people-please is out of control.

Wanna know the most ironic thing? You do the people-please in order to please, but nobody is happy … and neither are your spreadsheets.  It’s like the more I tried to please, the more displeased people became.

The antidote? Self-awareness, contentment with your own self [like, real contentment], and a surrender to higher reality.

In other words? Get yourself a confidence coach and/or a therapist.

If you need monetary inspiration? TDP is getting back on track to profitable times again, and that’s genuinely got a lot to do with my saying “enough!” to people-please: it pleases nobody, long-term.  

I promise.


Growing a team? You’ll need to develop the courage to be disliked


This has been one of my hardest lessons, honestly … but I ended up making basic maths peace with the fact that if I’m walking into a business with 20+ people > every day? Well, basic maths would tell you that it’s literally not possible to be liked by 20+ people > every single day.

I don’t know why I found so much peace in this realisation, but when I realised I was trying to win something that wasn’t mathematically possible? … I well and truly surrendered to the basic-maths-fact that I’m going to walk into my own business > daily > and have 2-3 [maybe more. #lol] people dislike me.

I can only hope that the dislike is short-term, and might perhaps have something to do with an unpopular decision I’ve had to make for the greater good … and so to speak to that? Nothing warms the cockels of my heart more than knowing that I went up against dislike because of an unpopular decision in the moment [that went on to become something that same person recognised as “the right decision” later on].

That’s the thing about unpopular decisions: you’ll have to make them.  You will.  And it’ll be based on you having full context on a situation that another person simply doesn’t have … and shouldn’t have, because they’re employee-side and didn’t sign up for the level of responsibility that comes with “full skin in the game”.

You did.

I’ll forever sleep well at night, even with the unpopular decisions, so long as I know I’m future-oriented and making short-term tough[er] calls for a much bigger overall good.

I can deal with that “dislike”, and will forever be able to … because I have to [and so do you].


You’re not the “friend”, you’re the “parent”


Wanna know what the loneliest feeling in the world is? … owning a business > employing the literal best human beings to work within it > looking at them all and thinking, “Christ, if I were employee side? I reckon we’d be best friends outside of this setting” > but knowing that when you’re leader and/or Founder? You just can not mix friendship[s] with work/your team/employees.

This is – hands down – the loneliest part of my TDP experience, but I countered this by joining a business mastermind with agency owners only … and yea, wow … founds me my antidote to Founder loneliness right there.

Not-the-friend-but-the-parent has never been more true for me than this year as I’ve stepped into my role as CEO > smack bang in the middle of an economic downturn [my mofo’ing timing. #lol] > staring down the barrel of some hard decisions, and even harder conversations.

And I’ve had to remind myself, regularly, that I can care with every fibre of my servant leader heart … but I’m not the friend, I’m the “parent” [more specifically, I’m the leader].

I can not begin to imagine how much harder this year would be for me if there was the blurring of lines [and friendship], proximity bias, and off the back of all o’ that? … favouritism [friendship + proximity bias = favouritism, whether you’re down for admitting that or not.  It’s true].


Leadership isn’t about you


Finally? I’m never not reminded of the truth of this lesson, but leadership isn’t about you.

Leading people well isn’t actually about managing them, and certainly not micromanaging them.  It’s not about coercion, and it’s certainly not about control.

You get the gist, yea? Like, it’s not about you … and it’s instead about a collective [yes, I’m acutely aware of how overused “collective” has become: particularly throughout the pandemic. #lol].  

For me? Whilst I might – by job title – be recognised as a leader at TDP, this has never been about me.  And never will be … because I’m instead part of a collective where it’s my role to inspire those within my team to push towards a shared ideal/objective/cause/mission/et. Al.

Leadership isn’t about you, and it’s not about what you get … but what you give [said every servant leader, ever].



Keen on following my CEO journey this year? I share a lot more about that via my personal LinkedIn page here.

You can either follow me there by clicking the follow button, or if you’re a little more extroverted? You can straight up hit the ‘connect’ button [lol].