The best part of working with highly ambitious people is that they’re driven towards achieving the best outcomes they can. They’ve usually weighed their options before they start working with me.
But here's where they get stuck: when their usual path or actions no longer work. They're scared of taking more risk. They don't want to admit that what they thought should work is no longer working.
These are people who made hard decisions in the past and navigated changing organizations. By this I mean they have wisdom and have learnt lessons from their adversities. Their experience and their wisdom is what made them successful up until now.
Earlier in their journey with a beginner's mindset, they had less to lose. They typically didn’t have a mortgage, a family dependent on them, or worrying about a retirement to fund. But it's more than just financial stakes.
When they’re starting out, failure is expected - even celebrated as learning. But once established, failure threatens their identity as someone who makes smart decisions. The same wisdom that got them here whispers: 'Why risk what's working?' Their past success becomes evidence that they should stick with what they know.
This creates a strange trap: the more successful they become, the more they have to protect, and the less willing they are to risk it all on something unproven.
What they don't realize is that inaction has its own price tag. While they're calculating the cost of taking action, they're ignoring the compound interest of inaction - the slow erosion of possibility, the gradual settling into 'good enough,' the quiet regret that builds when they know they’re capable of more.
Yet, every now and then they get to a fork in their life and career, that sometimes requires taking on more risk than they believe they can handle.
This awareness is essentially what drives them to seek out for external help to get them unstuck. They ruminate on this idea of what next, or know what is next, but are scared to bet on themselves.
The outcomes are uncertain, the risks are higher and hence the fear.
That’s the thing with risks, until we don’t take a step towards it, its hard to see the staircase.
The question I like to ask of someone considering a life-altering risky move: “What’s the worst that can happen if it didn’t work out ?”.
Most times, the story they tell themselves is worse in their head. Once they say it out loud and logically think through it, it is easier to mitigate or have a plan for each scenario. They can think through some realistic timeframes, and have a reframe of testing out some experiments to lessen the risk. This is when they can actually imagine taking that next step.
Not everyone’s story ends in success - it could end in lessons instead. But most people know that they can adapt to whatever comes next and keep moving forward. It is their innate resilience.
It is after this realization that a path becomes more clearer, more possible.
There have been many times when I wasn’t 100% confident on making a decision. I had doubts. I had to ask for what I wanted. But I also knew this: I couldn’t stay in the same place and expect a different outcome. Not all my decisions had the desired outcomes. Yet, I was glad I made them. Sometimes I wished I had taken an even bigger risk, sooner.
For where you are now, you have taken some risks to get here. Imagine if you had taken a bigger bet on yourself and risked more, what could have happened.
Here's what I've noticed: my most successful clients aren't the ones who were fearless about risk. They're the ones who became more afraid of standing still than moving forward. They realized that the 'safe' choice was actually keeping them from growth.
The question I like to ask someone considering a life-altering risky move: 'What's the cost to you of not taking that risk?'
The discomfort of risk is real. But so is the pride that comes when you back yourself and do something that scared you - regardless of the outcome.
Take the bet. You might just surprise yourself.
Hi, I’m Dipti, and I work with ambitious professionals navigating growth and change. Each week, I share practical insights, personal stories on leadership and intentional living.
If you enjoyed this read, please tap ❤️. Send me your questions at diptipatel@substack.com.
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