Stretto Strategies turned five this year, and I’ve never really shared much about my journey as a self-employed strategic communications consultant. But hitting the five-year mark — something I doubted many times — feels like a milestone worth recognising. So, brace yourselves; this is a long one.
The path to running my own business
I never imagined I would work for myself. That always seemed more suited to my driven husband (shoutout to David Oberholzer). But looking back, the path to Stretto Strategies started long before I even realised it.
During my Honours degree in Communication Management, and later my Master’s in Strategic Communication, I was fascinated by how broad the field was. Crisis communication, PR, social media strategy, content writing, corporate communication, and consulting — the list goes on. I was particularly passionate about integrated reporting and corporate social responsibility, even dedicating my thesis to it. But finding a career path in that space proved difficult. The feedback was always the same:
“Your CV is too boring. You don’t have enough experience.”
My dad and husband planted the idea of starting my own business in early 2019. For months, I thought they were crazy. Sure, I had worked throughout my Master’s, taken on internships, and done my fair share of odd jobs — but what exactly would I offer?
In December 2019, I took the leap and registered my business. By 1 January 2020, I was officially in business and on my “entrepreneurship journey.”
The self-employment vs entrepreneurship realisation
I started with big dreams, excited to build something meaningful. But a few months in, I had a realisation that changed how I saw my journey.
While working on one of my first projects with FluidRock, I came across a video by Vusi Thembekwayo. He made a distinction that hit me hard:
“Could you take three months’ leave and your business still meet its performance targets? If you can’t disappear from your business for 90 days, you are not an entrepreneur — you’re what we call self-employed.”
Three months into my so-called “entrepreneurial journey,” my identity was shattered. I’m not an entrepreneur. I’m just self-employed.
But I quickly realised — that’s not necessarily a bad thing.
The best (and sometimes worst) part of self-employment is that you have to do everything. You’re the strategist, the salesperson, the accountant, the compliance officer and the admin assistant all rolled into one. The experience and lessons I’ve gained have been far greater than I could have ever imagined.
So, after five years of learning, making mistakes, and figuring things out as I go, here are some of my biggest takeaways.
Five (plus one) lessons from five years of self-employment
1. Get a Personal Board of Directors
This isn’t about hiring an actual board — it’s about having a core group of people whose advice you trust. Mine includes my husband, my parents, my gran, and some incredible industry mentors like the late Clive Weil, Michael Judin, Leigh Roberts, Ronelle Kleyn, and Shaila Jivan. You need people who will be honest with you, listen when needed, and challenge you when necessary.
I also could not have done this without my Christian faith — prayer has been a constant throughout this journey.
2. Get an accountant (and learn the basics yourself)
“Register a company, they said. It’ll be easy, they said.” Lies.
For the first eight months, I did my own accounting because I wanted to understand my business finances. But at some point, you need to surround yourself with experts. Understanding your financial and fiduciary duties is crucial. I’m not an accountant, so I found the right team to support me.
Massive thanks to Tiaan Booysen at ProfitPro Accounting for making sense of the numbers and to the team at FluidRock Governance for teaching me about my responsibilities as a director and shareholder.
3. Know what you’re good at — and where you need help
I follow a consultant model. If I don’t have the skills, I bring in people who do.
I work with legal consultants, designers, and subject matter experts. There’s no need to do everything yourself — knowing when to collaborate is key to delivering the best results.
4. Learn to negotiate (even if you hate it)
Let’s be real: I’m a people pleaser.
Negotiating contracts and pricing was one of the hardest things I had to learn. How much is fair? Should I discount my rates? Am I overcharging or undercharging?
Over time, I’ve learned to track the time I spend on projects. Even if hourly rates aren’t always feasible, knowing how long things take helps you value your work properly.
My biggest negotiation tip: Always set your price with confidence — and stop talking after stating your rate. I struggle with this (ask those close to me; I love filling the silence). But one of the biggest mistakes I’ve made is rushing to justify my pricing or offering a discount before the client has even responded. State your fee, then wait. Let them process it and provide feedback. The answer isn’t always no!
5. Cut out the noise
Over the years, I’ve received plenty of (sometimes unsolicited) advice — some of it useful, some of it not.
“You’re trying to do too much.”
“Your CV is boring.”
“I wouldn’t pay more than R200 an hour for your services.”
“Communication? Anyone can do that!”
“ChatGPT will replace you.”
Some of it was valid. Some of it wasn’t. But if you stop for every negative comment, you’ll never move forward. Reflecting on all the comments I now know to:
• Take constructive criticism on board, but don’t let it paralyse you.
• Keep learning, reading and improving your skills.
• Surround yourself with people who push you to grow.
6. Set boundaries (and learn when to say no)
When you’re starting out, it’s tempting to take on every project, even the ones you aren’t equipped for. But compromising quality due to poor planning is a sure way to lose trust – and trust is hard to rebuild. Saying no is tough. I still struggle with it. But I’ve learnt to:
• Practise saying no in the mirror (yes, really).
• Ask my personal board of directors for guidance.
• Pray about big decisions.
You can’t deliver your best if you’re constantly overwhelmed.
Final thoughts
You will make mistakes. Some projects won’t go as planned. But the key is to learn, re-evaluate, and try again.
These past five years have brought challenges, growth, and opportunities I never expected. I’ve worked with amazing clients, both locally and globally, and I can’t wait to see what’s next.
Here’s to the next five years.
Stretto Strategies 