Everything I've learned about failure (from building a startup with +4 million users)

“Ever tried. Ever failed. No matter. Try again. Fail again. Fail better.”

Samuel Beckett’s famous words have a nice ring to them. And for a long time, they’ve permeated the wider circles of entrepreneurship as a kind of Silicon Valley mantra.

Failure is necessary. Failure is humbling. Failure is, almost — trendy?

At least on the outside.

Backstage, we scramble hysterically to avoid it at all costs. After all, businesses rely on consistency, predictability, and success — the opposite of failure.

And let’s be clear. Taking a glib, cavalier attitude toward failure is dangerous.

Entrepreneur-turned-VC Mark Suster argues that the Fail Fast mantra is:

“Wrong, irresponsible, unethical and heartless. Tell that to the person who wrote you $50,000 of their hard earned money and entrusted you to try your best. Fail fast?”

And failure certainly isn’t something to seek out. But it is inevitable. And with the right perspective, it can be transformed into something altogether more positive.

Throughout the 12-year process of transforming Jotform from a fun side project to a 110-employee business that serves 4 million users, I’ve navigated many failures: often laughably small, occasionally worryingly big.

Here’s everything I’ve learned.

1. Your reaction to failure matters more than…

When we hear billionaire moguls like Richard Branson or Jeff Bezos wax lyrical about the benefits of failure, what they really mean is this:

As an entrepreneur, you need to be prepared to experiment; to take risks that don’t always pay off.

Launching a startup sets you up for a sky-high chance of failure: from the dreaded 90% club to the inevitable roadblocks throughout the rest of your journey, it just comes with the territory.

What matters, then, isn’t whether you manage to avoid failure altogether — but how you react to it when it does.

There’s no way that you can live an adequate life without many mistakes. In fact, one trick in life is to get so you can handle mistakes. Failure to handle psychological denial is a common way for people to go broke.”

  Charlie Munger

We can let failure drag us down. Or, we can let it shape us.

Here’s the thing: growth and comfort cannot coexist.

And when we fail, something inside us inevitably changes. And by embracing that feeling of change instead of fearing it, we can use it to our advantage.

Ray Dalio, founder of Bridgewater Associates, discusses this sensation in his book, Principles:

I call the pain that comes from looking at yourself and others objectively ‘growing pains,’ because it is the pain that accompanies personal growth. No pain, no gain.

It’s no coincidence that the most successful people have also failed the most:

Richard Branson oversaw Virgin cola, cars, and wedding dresses crash and burn. 

James Dyson made 5,127 unsuccessful prototypes. 

Thomas Edison tried over 1,000 patents.

Even Jeff Bezos endured the spectacular flops of Amazon Auctions and Amazon Z.

Did they seek out failure? No. But they took an experimental approach that ultimately led to incredible achievement amongst the failures.

As 3M’s William McKnight once said,

The best and hardest work is done in the spirit of adventure and challenge… Mistakes will be made.

2. Have a light touch

Some ideas look fantastic on paper and then nosedive. Others seem like flash-in-the-pan madness, and then go on to make millions.

Basically, it’s impossible to predict how your market, circumstances, and customers will change.

As Paul Graham once remarked:

You haven’t really started working on [your idea] till you’ve launched.

When you devote a ton of energy, time and money into something, you develop a strong sense of ownership towards it.

It becomes your baby, a little seedling of hope. Naturally, it’s hard to let go of.

But attachment clouds judgment. It causes smart entrepreneurs to cling to ideas well past their sell-by-date, hoping for a sudden return on investment.

The prospect of failure takes on a very different form when it’s not costing anyone their money, or their time, or their sanity.

So start projects with a light touch and an open mind. I can vouch for this approach: Jotform started as a pressure-free side project, which meant I could test it as a fun hypothesis rather than a serious source of income.

Learn to be hyper-frugal with time, finances and resources; at least in the early stages of a venture.

Then, if it flops, it’s less of an ego blow, more of a learning curve.

Failure becomes part of a positive feedback loop.

Plus, testing quickly and cheaply gives you scope to try a different, better idea. Soon.

Being completely consumed by an idea is exciting — but risky.

Keep it casual.

3. Rock bottom = a foundation

Travis Kalanick’s first startup declared bankruptcy before he founded Uber. 

Oprah Winfrey was fired from her job as a reporter before she became a household name. 

Steve Jobs was forced out of Apple before making a glorious comeback.

When we see people doing incredible things, we forget they often started from nothing — or worse.

We see rock bottom as a conclusion. But if you look at it from another angle, it’s a foundation.

That’s because falling down — however humiliating it may feel — has positive side effects. It forces us to start afresh. It breeds humility.

Failure simplifies by process of elimination. It removes excess noise and hurdles, giving way to greater movement.

Another consequence of failure is total freedom. With nowhere else to fall, we can let go.

Losing everything should never be glorified. But we must remember that we can build from the ground up.

4. Limitations illuminate

Failure hurts because it strips away.

But when we’re left with the bare bones of an idea, something magical can happen. We’re forced to endure limitations and do more with less.

I’ve learned first-hand how limitations can illuminate and create a new direction.

When I was building Jotform — a bootstrapped company — I had the absolute bare minimum to work with: no outside investment, no mentors to guide me, no plan B.

It was tough. It was terrifying. But in the long run, it helped me.

These constraints made me super-thrifty, squeezing every ounce of value from the situations I found myself in. I had to think creatively, living firmly outside the box in order to survive.

It’s easy to assume that more is more — more money, more support, more time — but in reality, a sense of abundance can be treacherous.

In The Paradox of Choice, Barry Schwartz points out how backward our thinking is.

He explains that, despite modern culture’s obsession with freedom of choice, more choice equals less action.

Learning to choose is hard. Learning to choose well is harder. And learning to choose well in a world of unlimited possibilities is harder still, perhaps too hard. […] But by restricting our options, we will be able to choose less and feel better.

Having too many options is paralyzing.

Instead, working with the bare minimum streamlines. It clarifies. It lets us see clearly.

Limitations drive resourcefulness and fuel inspiration.

Learn to see them as a blessing, not a curse.

5. Know when to be flexible, know when to persist

Every successful person has had moments of self-doubt but persevered.

Grit and determination — even in the face of brutal knock-backs — are crucial to realizing an ambition. But equally, “never give up” is terrible advice.

It’s just as important to know when to pivot, adjust — or bow out altogether.

So how do you know when to stick with it, and when to quit?

James Clear suggests you identify your ‘non-negotiable’: the one thing you are not willing to budge on. No. Matter. What. Then, lose the obsession with everything — apart from this.

It’s easy to get attached to a particular version of an idea. And if it doesn’t pan out the way you’d expected, or planned, you might feel tempted to give up.

For instance, your non-negotiable could be running a profitable business. But there are thousands of ways to achieve this that don’t follow the conventional trajectory; you just need to be open-minded.

I like Jeff Bezos mindset for Amazon:

We are stubborn on vision. We are flexible on details.

So, you might accept defeat on a version of your idea; but that doesn’t mean you need to quit.

You’ve just gone slightly off-script. Get up, dust yourself off and try a different version.

Once you change your perspective on this, you will be able to see mishaps as interchangeable details rather than abject failures.

Harry Potter was rejected by 12 publishers before it was picked up by Bloomsbury for a £1,500 advance. Today, the combined series is estimated to have sold close to 400 million, making it the best-selling book series ever.

Imagine if JK Rowling had given up after her 3rd, or even 11th attempt at submitting it? It seems crazy now, but the prospect isn’t unreasonable.

If you believe what you have is worth showing to the world, endurance matters.

If you try once to get a ball in a hoop, it’s likely not to go in.

If you try a hundred times, it will.

Persistence increases your odds of success. So be resolute in your non-negotiable. Stick with it.

And be open to getting everything else wrong.

6. Failure delivers knowledge

According to Harvard Business Review, of the main reasons companies struggle to grow is due to fear of failure, with risk-averse working cultures blamed for lack of innovation.

But failure is impossible to avoid. And by identifying where things went wrong, we can extract extreme value from tricky experiences.

Failure shouldn’t be underestimated; but it shouldn’t be feared, either. Because mistakes are an opportunity to adapt, learn and grow.

Ed Catmull, Pixar’s president, agrees:

Mistakes aren’t a necessary evil. They aren’t evil at all. They are an inevitable consequence of doing something new… and should be seen as valuable.

Track and measure projects from the beginning. If things don’t work out, you’ll have a clear indicator as to why.

Crystalize these insights. Look for patterns. Develop a formula to follow next time round.

Reflect on positives, too. Ask for feedback and share your thoughts.

There’s so much to be learned about ourselves and others if we can push past the discomfort of examining our failures.

Worst case scenario, we make sure it doesn’t happen again. Best case scenario, we gain knowledge we can apply to other areas of our life.

Sign off

It takes guts to stick with a venture through thick and skin.

But it takes just as much courage, if not more, to know when to duck out, conduct a post-mortem, and move on.

We shouldn’t glorify failure. But we should celebrate the resilience it takes to bounce back.

Growth occurs alongside discomfort. Boredom and frustration are the foundations of incremental improvement.

And sometimes, you need to go back to move forward.

In other words, what feels like failure is often success in disguise.