Fail Like Churchill, Please!

Failure. The word alone makes anyone shift uneasily. Thanks to an archaic education system, social norms, and the modern quest to ‘win’ at any cost, we've been conditioned to see failure as an irredeemable red mark. It is a fictional ghost that haunts, but in reality, failure is always intermittent, and often, it’s the most enriching part of the journey.

I recently watched a lovely wartime movie, ‘The Ministry of Ungentlemanly Warfare,’ which made me want to learn more about Winston Churchill. A name synonymous with wartime leadership and indomitable spirit, but few recall how many times he fell flat on his face. Not only did he fail his entrance exams to the British Royal Military College—twice, but his early political career was a carousel of blunders. His biggest flop? The Gallipoli Campaign—so bad it almost ended his career. 

Many in his place would have given up, content to fade into oblivion. But Churchill had something most don’t - a willingness to absorb failure as part of the process. Instead of crawling into a hole, Churchill learned from his epic failures. When history came knocking, he was ready.

He famously said, “Success is not final, failure is not fatal: It is the courage to continue that counts.”

My rejection emails to startup founders who fell short of venture funding considerations on our investment platform always had a signoff message that I truly believe…A setback is a setup for a comeback. See you soon again!

Own Your Oops & Keep Walking

A 2019 study from Northwestern University examined over 700,000 scientists and found that those who failed early in their careers were more likely to achieve significant breakthroughs later than those who found early success. Those who failed and kept going developed a kind of failure immunity; they learned to pivot, adapt, and persevere.

Here’s how to channel your inner Churchill and make every stumble count.

Ctrl - Alt - Shift > Mindset

Instead of dwelling on the past and what-ifs, focus on the rich toolkit that failure often leaves behind. Thomas Edison famously quipped, “I have not failed. I’ve just found 10,000 ways that won’t work.” Failure becomes a stepping stone when we view it as a part of a broader timeline, not as the final chapter.

Step 1. Objectively analyze what went wrong and why. This will help you internalize the lessons and improve your chances the next time. This is gold.

Troubles Are Teachers, Say Thank You

Failure stings, but that’s a feature, not a bug. Churchill didn’t cry over his screw-ups—he used them as fuel. You can fortify yourself with past mistakes and equip yourself with resilience and perspective that only failure can teach. 

Step 2. Thank your detractors and all those who made you taste this rich flavor. If Gandhi had not been thrown off the train in South Africa, India might have lingered much longer under British slavery. Trust the divine interventions.

Timing is (Almost) Everything

Timing is an often overlooked element but can be as crucial as effort. The tech bubble of the early 2000s. Webvan, the online grocery pioneer, is often cited as a monumental failure, having burned through $1 billion only to go bankrupt in three years. But was it a failure in concept, or just a company ahead of its time? Fast forward to today, and the likes of Instacart thrive using a similar model. Timing, it turns out, isn’t everything, but it’s close. Research by Bill Gross points out timing too.

Step 3. Reframe the failure. See it in the context of macro events and related timing factors. Sometimes, your success doesn’t follow your schedule. Don’t judge yourself.

Persistence Beats Perfection

Churchill was relentless. He didn’t need to be perfect—he just needed to keep going.
Forget perfection. Focus on progress. When you stumble, pick yourself up and try again.

I love the concept of increasing the Surface Area of Luck. It is the amount of action you take around your passion and the number of people you communicate it to. The equation is L = D x T, where L is luck, D is doing, and T is telling.

Step 4. Start a side project, volunteer, and meet new folks. What seems like a mess now is likely preparing you for greatness later. Keep showing up.

Fail Forward, Expect Miracles

How they interpret and leverage their failures separates stagnant people from thrivers. It starts with acknowledging that failure isn’t a verdict; it’s feedback. Setbacks are not fatal flaws—they’re chapters in a story still being written.

Churchill once put it, “Success consists of going from failure to failure without loss of enthusiasm.” And that, my friends, is how you turn failure from a dreaded foe into a trusted ally on the road to triumph.

You’re just warming up for your finest hour. 

^{Image Credit - Artist Yuvi on Clarendon}

I teamed up with seasoned founders, investors, and experts to create an ‘Idea to Startup in under 15 weeks’ co-pilot program. It’s for corporate warriors who want to create their venture without leaving their golden nest. This program will help you ideate, build an MVP, validate, launch, and get the tricks of this opaque world of venture capital and innovation economy. Rose-tinted glasses are not enough to survive in the wild. 🙂 

Email me for a 20 minute 1-1 discussion to learn the details > [email protected]

___Why is it called /SALTT______________

^{In Roman times, salt was prized as much as gold—it was essential and invaluable and paid as a “salary.” To “earn your salt” is to add real value, which is crucial. The phrase still resonates today, but perhaps with an even deeper meaning. Earning our salt is not about compensation only—it’s about contribution, fulfillment, and the courage to live with intention.}