When You Keep Failing: How to Recover and Boost Your Confidence


“Success is a series of small wins.” ~Unknown

You tried everything. Nothing worked. What now?

I was the Marketing Director of a tech startup, and my work wasn’t bringing in the money or traction that it should. I did everything to improve my results: I read more books, consulted mentors, changed my mindset and tactics, did more field research and experiments, consulted even more books and mentors.

I won’t go into specifics, as that’s not what this article is about. But suffice to say that I did my best to learn from every book, mentor, experiment, and mistake. And I executed all the best practices. But after months of fruitless efforts, the CEO finally let me go. I didn’t contest it. Even I would’ve resigned out of shame for my results.

I went back to freelancing. After two months of rejected or ignored client pitches, I updated my profile on job search sites. Four months later, I was broke and still unemployed. One more month and my landlady would kick me out.

I remember one night, after another day of sending out client proposals, job applications, and going door-to-door to different shops in various neighborhoods to offer my services (and getting rushed out of each), I passed a group of college girls wearing preppy summer dresses. They looked young, carefree, on top of the world. I was the exact opposite: bent, worried, defeated, alone.

I went home, ate some muesli with milk, and poured my feelings on an article. It was the only form of self-comfort I could afford.

At that point, I’ve been losing and failing consistently for more than half a year. I’ve searched things like, “How to fix a failed career” or “How to rebound from failure” or “How to get back up when life kicks you the f**k down.” With plenty of other variations.

And this is going to sound very biased, but I read almost every article that those search queries produced, and I executed almost all of their tips. Yet, nothing worked.

I was hit by the sobering reality that it’s very possible to consistently do your best, to work so damn hard, to put your soul into something, and fail.

When you’re stuck and you feel like failing has become your “new normal,”  how do you recover and get back up?

Remind yourself what winning feels like.

I ran a 12-kilometer mountain race  once. It was my first 12K run and my first mountain race. I didn’t know if I could do it. I was unfit and overweight at the time.

During the first five or so kilometers, I was wheezing and ready to give up. But as I kept going, I started to feel better. My steps flew faster. And I finished the race among the top twenty.

There was a moment in the race where I ran an uphill climb. My lungs and legs felt great, and I kept overtaking other runners. Eventually, I passed all other runners in sight and I was running the trail alone.

On top of the climb, there is a clearing. I reached the mountain’s peak and, below me, blades of tall, soft Tiger Grass danced with the breeze. The sun was rising. Rays of light glinted across the swaying field, iridescent. The wind blew. I stared into the horizon and the word “triumph” flashed in my head.

Time passed and I eventually forgot that memory as I got immersed in my work. But it resurfaced one night, as I ate muesli with milk alone in the gloom of my apartment.

We all need to remind ourselves what winning feels like sometimes.

See, you can’t go to a job interview or a client presentation feeling like a loser. It would reflect in your body language, vibe, and energy. Soon, you’ll walk, talk, and think like a loser. Even when you’re doing your best.

So you need to break out of that. And my experience taught me that the best way to do this is to give yourself small victories.

Ideally, you can gain those small wins in the field you’re pursuing. Let’s say you’re trying to get big-brand clients for your business. If you achieved a few promising meetings, then it’s great.

But what if you can’t get anything in the field you want? Like me, with my consistently rejected or ignored client proposals and job applications?

In my case, the memory of that 12K triumph was the first step. If I couldn’t get a small victory where I wanted it, then I can get it somewhere else.

So I ran. Three to four times a week. And with every run, I’d give myself a goal: Maybe finish a difficult 10K route in one hour, or run a pace of six to seven minutes-per-kilometer for three hours, etc.

Every time I achieved my goal, I was gaining small victories. Sure, achieving those victories didn’t directly get me a client or a job. But it reminded me of what it feels like to win. Bit by bit, it rebuilt my confidence and energy.

Small victories aren’t empty words of encouragement. They’re real. And they helped me believe that I can achieve things again.

How to Get Back Up After Continued Failure

1. Accept that it’s possible to fail even when you’re doing your best.

This was the biggest shocker to me. I always believed that if I did my best, I’d get what I want.

So when all my attempts at the tech startup, at getting clients or work failed, I started to seriously doubt myself. Maybe all my ideas suck? Maybe what I’m doing is all wrong?

Maybe I have the Midas touch, but reversed; everything I worked on turned into stone, not gold.

Yes, there’s likely something wrong with my mindset, or how I executed things, or the kind of solutions I came up with. And I needed to change and adjust.

But I had to accept that, sometimes, we don’t control everything.

Years later, as I looked back on my tech startup failure, I realized that there were external factors I couldn’t do much about; accessibility of certain technologies, governmental policy norms, the readiness of the target market, and so forth. It was also the first startup I worked with. I had to constantly adjust and make my own solutions. No wonder I failed.

Likewise, I was able to defeat the thing that kept me from getting jobs or clients: My stubborn pride. Before the tech startup, I worked almost-exclusively with big-brand clients. I was young, ambitious, and making a lot of money. Why should I apply for anything less? So I pitched only to the biggest clients and applied only to the highest paying jobs.

When the reality of losing my apartment finally kicked me in the head, it was too late. Thankfully, the piece I wrote when I passed those college girls in their preppy summer dresses, was published by a national paper. And several kind-hearted business owners who read it gave me work (bless them forever). So I survived.

2. Achieve small victories where you can.

When you’re aiming for small victories, aim to win against yourself, not other people.

In this context, don’t feed yourself feelings of victory by winning against others. First, it’s unsustainable. Second, it won’t build the confidence you need.

Bottom line: Achieve small wins from self-imposed goals that are purely for you and about you. No other people in the picture. No trying to win someone else’s approval. And don’t go for outcomes you don’t control.

I’m currently writing my first novel. I’ve worked on it almost every day, for two to four hours a day, in the past seven months. So far, I’ve written and thrown away three drafts. I’m on my fourth draft, and I might throw it away too. I feel like a failure for not completing what I set out to do.

So I’m gaining small victories on Medium. I’ve started blogging this January, and I’ve committed to publishing a minimum of two articles a month while working on my novel and my client work.

Whenever I publish a full article, I feel good about myself. Sure, maybe no one would read my posts or engage with them (aside from a few supportive friends). But I’ve achieved my goal, and this small victory keeps me going.

If you’re reading this now, maybe you’re in the same phase in life. With that, I sincerely encourage you to gain small wins. Start small and grow your victories from there. I genuinely wish you all the best. Keep strong! Triumph!


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