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Part 2 of 3: The Lessons

This is the second in a three-part series. In Part 1, I shared the story of my leap into self-employment. Here, I break down the key lessons I learned—and offer a personal exercise to help you map your own safety nets before making a big change.

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The Foundations of a Bold Career Move

In my previous article, I detailed the intense personal circumstances that led me to take the terrifying leap into self-employment. The ultimate decision was an emotional reckoning, but the journey that followed taught me profound, practical lessons that apply to anyone facing a critical career or life transition.

Here are the three most important insights I gained—the ones I wish I’d learnt much sooner.

Three Key Lessons I Learned

1. Fear of Failure is Natural, but It Can Be Overcome
That paralysing fear of failure can hold us back from taking necessary risks. For me, that fear was tied directly to my past and my children’s stability. However, by focusing on the bigger picture—the undeniable need to provide, and the support system my mother created—I was able to push past my fears and take the leap.

2. Having a Support System Makes All the Difference
My mother’s unwavering support and wisdom played a pivotal role. She didn’t just give me advice; she created a practical financial shield that allowed me to fail without catastrophic consequences. A strong support system—whether it’s family, mentors, or friends—can provide the courage and reassurance needed in difficult decisions.

3. The Importance of Cash Flow
In business, the focus shouldn’t be solely on securing new contracts or sending out invoices. The real, often painful, challenge is ensuring that clients pay on time. My uncle’s practical warning proved true: the excitement shouldn’t be about invoices going out, but the money coming in. Managing cash flow is absolutely crucial for long-term success and survival.

Three Key Learning Points

These personal lessons translate into universally applicable wisdom for tackling risk and change:

1. Support systems can enable bold decisions: The presence of my mother during this transition provided both emotional support and a practical safety net. We often need others to help us take that leap of faith by minimising the perceived consequences of failure.
2. Practical business wisdom matters: Focusing on the money arriving—not just the billing—is the difference between theoretical business success and actual, bankable financial stability.
3. Work flexibility can align with life priorities: The freedom to structure my work around caring for my family demonstrated how self-employment can provide a level of control that traditional employment often can’t, allowing me to put my priorities first.

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Your Action: The “Safety Net Exercise”

This one’s personal. Grab a cuppa and settle in—before you can help your organisation map its safety nets (we’ll get to that in the next article), you need to understand your own.

This exercise is designed to help you quantify your risks and fears before making a big change in your life and career.

1. Map Your Support System
Take a piece of paper and create a mind map or a simple list. Don’t just list your assets; list your safety nets.

2. Identify Four Critical Areas
For each area below, write down every resource you have available. Be honest and thorough:

• Emotional Support: Who could provide genuine, non-judgemental backing during a stressful transition? (e.g., a friend, a mentor, a partner)
• Financial Resources: What specific resources could you access if needed? (e.g., emergency savings, an available credit line, a spouse’s income)
• Transferable Skills: What skills do you already possess that are immediately marketable or valuable to a client? (e.g., project management, grant writing, team leadership)
• Knowledge Gaps: What specific, practical knowledge would you need to acquire before taking the leap? (e.g., tax law, marketing basics, accounting software)

3. Reflect and Assess
Once your map is complete, ask yourself: How does the presence (or absence) of a strong net in one area influence your willingness to take a risk in another?

Missed Part 1? Read it here – https://theartofstupidity.com/2025/10/31/article-1of3-tough-decisions/