Most advice about career changes focuses on two moments: the decision to leave, and the success that follows. The missing piece is the expensive middle, the part that takes years, costs everything, and teaches you more.

I spent three and a half years trying to pass a real estate licensing exam. During that time, I burned through my savings, worked as a food delivery rider, crashed a motorcycle, and watched my family’s income drop to zero. When I finally passed in 2022, people congratulated me on my perseverance. But what I actually learned had nothing to do with perseverance. It had to do with why we lie to ourselves about what career transitions actually require.

The myth of the clean break

The narrative around career changes has become dangerously sanitised. Someone quits their corporate job, discovers their passion, and six months later, they’re thriving. The timeline is neat. The arc is clean. The lesson is clear: just take the leap. This story is misleading and expensive. Because it convinces people that if their transition isn’t working within a reasonable timeframe, something is wrong with them rather than with their expectations.

Here’s what a more honest timeline looks like: In 2019, I left my role as General Manager at Singapore Sports School because I wanted more time with my young children. I enrolled in a real estate course, assuming it would take a few months. I failed the exam twice that year. I quit my job to study full-time in December. Then COVID-19 hit, the exam was postponed indefinitely, and my household income disappeared.

By April 2020, I was delivering food on a borrowed motorcycle, hiding my identity under a full-face helmet. During one rush delivery, I crashed. A metal barrier sliced my arm open to the bone. I rode myself to the hospital, bleeding the entire way.

That’s the expensive middle. And almost no one talks about it honestly and openly.

Why the middle costs more than you budget for

Career transitions fail not because people lack commitment, but because they underestimate three specific costs:

• Identity loss: When you leave a stable role, you don’t just lose income; you lose the social proof that validates your decisions. I went from General Manager to a food delivery rider. Every shift felt like a public failure. The helmet wasn’t just safety equipment; it was a way to hide from people who knew me. That psychological cost compounds daily in ways financial planning can’t capture.
• Decision fatigue under pressure: When I lost my savings through failed day trading attempts, I wasn’t making rational choices; I was panicking. The stress of providing for a family while repeatedly failing creates a decision-making environment where mistakes multiply. You’re trying to think strategically while in survival mode. These are incompatible states.
• Relationship strain: A friend once told me, “If I were your wife, I would have divorced you for putting the family through this.” That comment reflected an uncomfortable truth: career transitions don’t just test you, they test everyone around you. The person changing careers bears the identity loss and decision fatigue. Their partner bears the anxiety of watching it unfold, often while holding the household together. Both costs are real.

Also Read: Rewriting the narrative about motherhood and career: Insights from a female tech leader

What actually keeps you going (it’s not motivation)

By my fourth exam attempt, I wasn’t motivated. I was exhausted. Motivation is what gets you to start. What keeps you going through years of failure is something else entirely.

Systems replace willpower. After failing three times, I stopped studying harder and started studying smarter. I found someone who had passed and asked them to coach me. I identified my specific knowledge gaps instead of reviewing everything. The shift was mechanical.

You stop comparing trajectories. I deliberately don’t follow other real estate agents on social media. Not because I’m uninterested in their success, but because comparison is a distraction I can’t afford. When you’re in the expensive middle, other people’s timelines become noise that drowns out your own progress signals. The discipline isn’t in working harder, it’s in ignoring what doesn’t matter.

You reframe failure as data. Each failed exam wasn’t wasted effort; it was an expensive education. By the fourth attempt, I knew exactly where my gaps were. The question wasn’t “why do I keep failing?” It was “What specifically am I missing?” This reframe transforms failure from evidence of inadequacy into evidence of incomplete information.

The hidden value of unreasonable timelines

Three and a half years to pass a licensing exam is objectively unreasonable. But the extended timeline created something I couldn’t have gained otherwise, which is the clarity about what I was actually building.

When success comes quickly, it’s easy to confuse luck with skill, or timing with strategy. When it takes years, you’re forced to separate what works from what doesn’t. You eliminate the variables. You test your assumptions under stress. You discover which parts of your plan were fantasy and which were foundation.

More importantly, the unreasonable timeline filters out people who aren’t serious. I don’t mean this judgmentally, some people realise mid-transition that the destination isn’t worth the cost, and that’s smart recognition, not failure. But for those of us who stay, the extended middle becomes proof of commitment that no amount of early success could provide.

What working parents face that solo founders don’t

The startup world talks a lot about founder resilience, but working parents face a compounding pressure that solo founders don’t: you can’t iterate fast and break things when “things” include your family’s stability.

Every failed exam wasn’t just a setback for me; it extended the period my wife couldn’t plan around. Every month without income wasn’t just financial stress; it was my kids potentially feeling the instability. The risk isn’t just yours to take.

Also Read: How to use AI positively and stay ahead in your career

This creates a different kind of discipline. You can’t pivot recklessly. You can’t “fail fast” when fast failure means your family loses their home. You have to balance conviction with responsibility, and that balance is more complex to strike than any business model.

My wife joined me in real estate in 2024, while pregnant with our fourth child. She passed her exam on the second attempt, studying late at night while caring for a toddler. The fact that she chose to enter the same uncertain profession, having watched what I went through, says something about how we evaluate risk differently after surviving the expensive middle.

What the expensive middle actually teaches

The lesson is about honest accounting. Most career transitions will cost more, financially, emotionally, and relationally than you budget for. The question is whether you can maintain clarity about costs while they’re accumulating, and whether you can separate sunk costs from future value.

I now help families buy and sell homes, and the skills that matter most aren’t the ones I learned studying for the exam. They’re the ones I learned in the expensive middle: how to stay focused when outcomes are uncertain, how to make decisions under pressure, how to communicate honestly about risk.

These aren’t skills you gain from success. You gain them from surviving the gap between decision and outcome.

If you’re in that gap right now, if you’ve left something stable and the new thing isn’t working yet, you’re not failing. You’re in the part nobody talks about honestly and openly. The part that costs more than you planned. The part that lasts longer than seems reasonable.

The expensive middle is where the real work happens. Not because it’s noble or character-building, but because it’s the only place you learn what you’re actually capable of building.

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