Top 5 tips from 8 years of coaching

October 2019 saw the end of a torridly wet winter. After 10 summers together in Sydney, it was time for a change, and Devonport was where we berthed on a frosty, foggy morning. There was a novelty in returning to seasons, an open fire, and the appeal of a real winter. My Irish background and my husband’s South Island childhood likely influenced our nostalgic leanings. And so, driving in convoy down the Midland Highway with two small children in tow, our cat of many lives, and our belongings somewhere in transit, we made our way to Hobart. No jobs, no friends or family—just a hunch and a desire to carve out our place.

While my husband developed his career in the kitchen, I knew life outside motherhood beckoned. So, not one to sit idle, I started a children’s blog, then got paid to write for another, which led to a stint at Fullers, marketing a baby carrier, co-producing a weekend market at Mona, and even a dip into business ownership. My curiosity and love of learning propelled me through this range of jobs, eventually leading to Digital Dandy, where I embarked on a career in coaching. Through it, I’ve had the opportunity to sit with, listen to, and encourage small businesses around Tasmania to believe in their work.

It has been eight years since I transitioned from student to teacher in the Tasmanian Government’s Digital Ready program. This program has enabled many hundreds of sole traders and small businesses to connect with a group of coaches, all of whom actively work as marketers. Experiencing it as a student and later as a coach has been thrilling, and the conversations I’ve had over the years give me a unique perspective on how just some of Tasmania’s 42,000 businesses feel about their products, services, and audiences.

Now, as the Digital Ready program draws to a close, I find myself reflecting on these years of conversations. I’m deeply inspired by the tenacity, courage, and strong will of the many business owners I’ve met along the way. For such a small state, Tasmania punches above its weight in small business. We have about 2% of all Australian small businesses, fitting for a state with 2% of Australia’s population.* Breaking it down, that’s about 1 in every 12 people owning a small business here in Tassie. Let that sink in!

As we wrap up these free mentoring sessions, I’d like to share some key insights I’ve worked on with clients. Judging by the numbers, perhaps you are one of the thousands of small business owners reading this right now.

Here are my top 5 tips from 8 years of Digital Ready coaching:

1. Why do you own a business?

Understanding your “why” keeps you grounded and motivated. This is often one of the first questions I ask a participant, and it’s where we spend the most time. Your “why” is what gets you up in the morning, keeps you up at night, and gives you the energy to continue when the days are long. What’s the point? There’s no one better than you to share the answer.

2. How well do you know your audience, your customers, and your community?

These connections are the heart of your business. We must spend time listening, questioning, testing, and measuring to know our customers in a way that makes business more than just money changing hands. People remember how you made them feel—and we all need those good feelings these days.

3. Overcoming the self-promotion “ick.”

You can promote your work without feeling uncomfortable—find what works for you. After understanding your why, we turn to how to express it, often confronting the discomfort of self-promotion. What if people think I’m growing my ego rather than my business? But what if people need a connection that may just give them the help they seek? There are ways to overcome the “ick,” but success only comes when you realize that no one else will tell your story for you.

4. Getting stuck in the trust rut.

Trust takes time but can be the foundation for business growth. In business, building trust involves reliability, respect, and a strong sense of community. A solid why, a deep understanding of your community, confidence in representation, and consistently showing up all play a part. Plan, practice, and purpose are the seeds; transformation and conversion are the fruits.

5. Planning—and following through with it.

A solid plan is essential for any successful business. Just make sure you stick to it! I used to be a terrible planner, keeping everything in my head, until I listened to my own burnout signals. Now, a plan is the anchor for every aspect of business, and I share this with my clients—especially those who feel time-poor or frustrated. A plan a day keeps burnout at bay, and checking in regularly on why it matters has been a game-changer for many.

Digital trends come and go like fast fashion, and often our brains—and our wallets—can’t keep up. The years fly by. Those little children we brought down from Sydney are now only a year or two away from finishing school. The cat finally used up her nine lives, and in her place, we now have a scruffy, opinionated, slightly anxious dog. Following a hunch turned out well for us: Digital Dandy celebrated ten years in 2023.

The biggest lesson of all? Without strong foundational insights, no amount of effort or reactive trend-chasing will lead to success. So remember to ask yourself: what is the point, what are my goals, and how am I going to reach them? If you’re keen to carve out your own place in Tasmania, take a moment. Have you found your people? Do you believe in your work? And what impact do you want to make? Getting clear on these questions allows everything else to fall into place.

While it’s disappointing to see this program draw to a close, here’s the good news: I’m not going anywhere! I’ll be continuing to offer private coaching in 2025.

Here’s what I’m offering in 2025:

1:1 Coaching (Bookings Now Available) 

Tailored one- or two-hour sessions via Zoom, designed to suit your business needs.

Group Coaching (Email me with your interest) 

A monthly program running over six months, starting in March 2025—perfect for diving deeper into strategy and sharing ideas in a collaborative environment.

*Australian Bureau of Statistics, Regional Population, 2021-22, Accessed 15 January 2024