Our Sidestep the Hustle Group Coaching Program
This is coaching shaped by experience, not trends.
I’ve spent more than 25 years working in marketing, brand, content and business strategy, and over a decade running my own business. I’ve supported founders through growth, plateaus, pivots, grief, business breakups, new family changes, ambition and reinvention.
Group Coaching exists because business is rarely just about tactics.
It’s about judgement. Confidence. Values. And having the space to think clearly when everything feels loud.
This is that space.
Kate Stokes, Coco Flip
“I really enjoyed connecting with Fiona and the other wonderful small business owners in the group. It was so helpful to discuss challenges with other people who were experiencing similar things and to have some accountability for my plans. It was so helpful to discuss challenges with other people who were experiencing similar things and to have some accountability for my plans. The program helped me step outside of my usual business practices and shake up our strategy. It gave me the confidence to make some big decisions and look to the future of the business. It can be difficult to carve out the time to really analyse where you are and where you want to go, and doing the program made it so much easier to protect that time.”
WHO IS GROUP COACHING FOR?
Sidestep the Hustle is designed for small business owners who want to work on their business, not just stay stuck working in it.
This is for you if you’re experienced enough to know that quick wins aren’t the whole picture, but you’re craving clearer thinking, better decisions and more confidence in the direction you’re heading.
You might feel capable, driven and committed, yet still find yourself second-guessing choices, comparing yourself to others or carrying the weight of your business alone.
This space is particularly suited to creatives, retailers, consultants, designers, makers and founders who care deeply about what they’re building and who they’re building it for.
People who want sustainability, not just growth for growth’s sake.
Depth, not noise.
Clarity, not constant urgency.
What changes when you’re in Group Coaching?
People don’t come into Group Coaching because they don’t know anything.
They come in because they know a lot, but feel overwhelmed, reactive or unsure which direction deserves their energy next.
What changes isn’t just your strategy. It’s how you relate to your business.
You start trusting your own judgement again.
You stop chasing every new idea or comparison.
You get clearer on what matters, what doesn’t, and what you’re willing to say no to.
This isn’t about fixing you.
It’s about giving you the space, support and perspective to lead your business in a way that actually fits your life, values and goals.
HOW DOES GROUP COACHING WORK?
Group Coaching is intentionally capped and curated to keep it intimate and thoughtful. Each group is made up of people who are committed to learning, challenging themselves and doing the work, guided by deep experience in small business strategy, systems, marketing and content.
The structure exists to support you, not overwhelm you.
Live Group Coaching Calls
You’ll join two one-hour live coaching calls each month, hosted by Fiona Killackey.
These sessions focus on the real areas that cause stress, confusion and stagnation in small business, from marketing and profitability to systems, decision-making and visibility.
They are practical, reflective and responsive to what’s actually happening in the room.
Tools, Training and Templates
You’ll have access to a comprehensive library of tools, templates and trainings covering marketing, money, systems, content and business models, so you’re not starting from scratch every time you need clarity.
One on One Support
Each member receives two 30-minute private coaching sessions with Fiona across the year, allowing space to focus on your specific business challenges, priorities and direction.
Courses and Chat Group
You’ll also receive access to all My Daily Business courses during your time in the program, including our monthly AI Chat Group, where we explore practical, thoughtful ways to use AI in your business without losing your voice, values or humanity.
Guest Expert Coaching
Across the year, you’ll learn from carefully selected experts in areas such as SEO, meta advertising, PR, brand collaborations, mindset and law. These sessions are designed to complement the coaching, not overload you with tactics.
Community and Connection
You’ll be part of a private WhatsApp group for ongoing peer support, conversation and accountability.
For many members, this sense of connection and shared experience becomes one of the most valuable parts of the program.
WHAT PEOPLE SAY ABOUT GROUP COACHING
Faustina Agolley, SuperFamily
“I’ve been an employee and a freelancer but I’ve never created a product based business that could scale. Superfamily had its branding on lock and a vision for haircare, but I was still asking “what on earth next? And HOW?!” Fiona is both a coach and a pro team player. The coach in her gives you a 10,000 foot view of your business, and the pro team player means she has endless solutions for the day to day challenges. Both of these modes of Fiona’s leadership allow you to grow so your business can follow with you, not the other way round. A special highlight of group coaching are the roster of other successful business owners that conduct “ask me anything” sessions.”
Lauren and Sofia, Leaf Supply
"We did our group coaching with you and it was a game-changer for us. When you're in the business, you don't always see things clearly. To have somebody who's like, “Maybe think about where your revenue is coming from, and if you're doing things for the right reasons” was amazing. It so was helpful to sit down, crunch the numbers and…. to cut back, streamline, and work out where we should be focusing on and what's important to us."
INVESTMENT
Sidestep the Hustle is a twelve-month commitment.
Your investment is AUD $699 + GST per month, or AUD $8,000 + GST paid upfront, which includes a saving.
This reflects the depth of support, experience and access provided across the year
A NOTE ON ACCESS AND INCLUSION
Each intake includes one fully supported place for someone working in a charity or not-for-profit, someone who is BIPOC, First Nations or LGBTQIA+, a single parent, or someone currently experiencing financial difficulty.
If this applies to you, you’re encouraged to mention it in your application. All information is treated confidentially.
BEFORE YOU APPLY…
This program isn’t for everyone.
Sidestep the Hustle is grounded in real frameworks, proven approaches and decades of experience across marketing, brand, systems and business strategy. You’ll be challenged to think clearly, make better decisions and take meaningful action in your business.
At the same time, this isn’t a program built around hustle-for-hustle’s-sake.
It’s not about working around the clock, burning yourself out or chasing growth that comes at the expense of your health, relationships or values. And it’s not a space where success is measured by how busy or visible you look from the outside.
What you will get is thoughtful, practical guidance that has been tested across different industries, business models and stages over more than 20 years. You’ll learn frameworks that work, but you’ll also learn how to apply them in a way that fits your business, your life and your goals.
This program is best suited to people who want to build something sustainable and considered, who are willing to reflect as well as act and who understand that strong businesses are built through both strategy and self-awareness.
If you’re looking for a place that combines experience, clarity and accountability without sacrificing your humanity, you’ll likely find this a very good fit.