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Avoiding the Downside Vs Achieving the Upside

How to achieve success by focusing first on not doing the wrong things than doing the right things.

For the past few months, I have been taking Tennis lessons. It’s a group setting and all students are at the intermediate skill level. Last week, during a typical drill session, all of us were hitting the ball into the net more often than hitting it across the net. Finally, the coach paused the drill and advised us –

“Just try to hit the ball across the net. It doesn’t matter if it’s IN or OUT. If you hit it across the net, there is a 50% chance that at least it will be IN. And there is another 50% chance that your opponent might make a mistake. So you have a 25% chance to win a point.

But if you hit the ball into the net, there is a 0% chance you will win a point. Your opponent doesn’t have to do anything to win points. She just needs to wait for you to continue to make mistakes.”

Unlike professional players, who play and place their shots wherever they want, amateur players make endless mistakes of hitting the ball into the net. Professional players win points. Amateur players lose points.

As our coach advised, to achieve success (i.e. to win a point), avoiding the downside (i.e. not hitting into the net) is probably more valuable technique than achieving the upside (i.e. hitting across the net and IN the court).

It is a step by step journey. In every step, you first try to avoid your downside and improve your chances of moving to the next step. The better you get at avoiding your downsides, the longer you stay in the game, and the closer you get towards your destination.

As you get better at avoiding downsides, and as it becomes the skill, you transition from being an amateur to being a professional. And when you become a professional, you start controlling your shots and focusing on achieving the upside.

As you begin the journey, at every step, it is quite clear what downsides you should avoid going to the immediate next step compared to what upsides you should achieve as it becomes apparent very sooner what is not working than what is working. The downside always looks clear. The upside always looks hazy.


As a startup founder, I can also correlate this advice on how we should run our business. The step one is always about what to avoid i.e. what not to do in your business to reduce the risk.

Some examples of things I carefully avoided since we started Avoma

  • not starting a company without co-founders
  • not jumping to building a solution without extensive customer research
  • not picking up a small market, etc.

I believe to win in the hyper-competitive market, you simply need to figure out a way to stay longer in the game. As long as we avoid making stupid mistakes of burning cash too quickly, building products that no one wants, etc., we will keep increasing our chances of winning in the market.

As long as you systematically avoid the downside in your life, you will continue to increase the chances of achieving your desired success.

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Why I Still Iron My Clothes Instead of Giving to a Dry Cleaning Service

And how it keeps me grounded, humble and calm.

It was a typical Saturday afternoon and I was lying on the bed thinking about what to do for the rest of the day. And I saw the stack of my shirts to iron has piled up in the corner. Looking at the size of the stack, I questioned, if should I iron these clothes at home, or should I give it to some ironing service.

After pondering for a while, questioning what’s my worth for an hour, searching for the closest ironing services on Yelp, I ended up deciding to iron the clothes myself only.

For the past 13 years that I have been living in the United States, I have NEVER given my clothes to any dry cleaning or ironing services.

In hindsight, it was mostly a cost-conscious decision in the early days. It typically takes me 5–10 minutes to iron a shirt. So on average, I can iron somewhere between 6–8 shirts in an hour. With $2/shirt, I was saving somewhere between $12–16/hour. And that’s not a lot saving considering what would be my hour worth.

Over the period I questioned if I am spending my time on the “right” i.e. “high leverage” activity, and instead if I should just give this work to a someone who’s specialized in this job. But every time I decided to give this work to an external service, I would get an inertia of searching for a place, commuting to drop the clothes and then again commuting to pick up the clothes, etc. Considering it would take at least 40–50 minutes in total just to give it to an external service, I would end up doing at home only.

And every single time I iron my clothes at home, it reminds me a story of an ironer from my small hometown in India.

The story of a an ironer from my hometown

I remember this ironer who used to come to our house to pick up all clothes, take it to his home, iron them, and then deliver back to our home. He ran this home-based pickup and delivery service for a couple years until he got enough customers from our neighborhood where he became the de facto ironer for most of the homes.

Eventually, he outgrew his business and built a small 3 ft. x 3 ft. iron sheets based shop near our house. It was a very tiny shop. It didn’t have anything other than — his ironing table, coal-based iron, and a kerosene lantern for the night. Now he stopped coming home, and we had to drop and collect the clothes at his place ourselves. He ran his operations from that shop for a couple years.

He again outgrew his business and bought a small 10 ft. x 10 ft. shop in a shopping center of our neighborhood. He then upgraded to an electric iron, had a light and a fan, 2 ironing tables, hired one additional helper, etc. His business was still growing. He looked very happy and satisfied with his hard work and the progress he had made so far.

All of this happened between my 6th grade to 11th grade. And one thing that did not change in these many years was — the person.

He was still the same hard working person I had seen him on the day one. He was still doing the ironing work himself every single day. He still had the same level of humility and humbleness even after achieving so much success.

Lessons learned from the ironer

And every single time I iron my clothes at home, I still remember him. I remember his journey, his hard work, his success, his humbleness.

Ironing my clothes keeps me grounded and humble. It makes me appreciate the journey of hard work to reach to your desired destination instead of being impatient and taking shortcuts.

But you might question if we would not have given our clothes for ironing to him and instead if we would have done it ourselves, then he would have never built his business. So if I give similar work to the local businesses here in the United States, then they could also build and flourish their businesses.

And I completely agree with that. The only rational argument I could use in my defense would be — the unit economics were very different for similar services in India vs here in the United States when I started working in the United States. And now, it has just become a habit.

I also find ironing my clothes a relaxing and meditating activity. You are focused on one task and are trying to do your job well done. Sometimes I also listen to podcasts or music or watch a movie on TV. That way the regret or concern of if I am spending my time on the right activity does not become a concern anymore.

There is also a sense of satisfaction after finishing ironing with the sight of a neat pile of freshly ironed clothes.

Closing thoughts

By any means, I am not saying this is “the” approach. This works for me — even though financially or opportunity wise it may not be a wise decision, but I’ve learned to find a good meaning out of this activity.

I hope you may also find any such activity that’s not worth doing yourself purely from a financial perspective, but may inspire you or just bring up the good old memories.

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The Delusion of Success and Failure

How Success and Failure are dependent on each other and are also tangled with each other.

I had shared this brief thought on LinkedIn the other day, but due to their number of characters limit for the post (BTW, it’s 1300), I couldn’t explain the thought in detail. So expanding it here.

The Context

A few days ago, I met a founder, who was very smart both academically and intellectually, and had raised a solid Seed round from Valley’s top-notch VC firms, but after 2 years of execution, they had to shut down the company.

In her own words, they failed to achieve a product market fit. They had built an innovative solution, which was looking for a problem.

In her defense, it’s not that they didn’t know how to identify a problem. She had read everything about Lean Startup, Customer Development, Paul Graham’s Startup essays, etc. and had done extensive customer development interviews. Despite all of this, they still failed.

While it’s one thing to learn these things in theory, it’s a completely different ball game to follow it in practice.

Failure?

Meanwhile, I kept thinking, did she really “fail”? And failed from what perspective?

If you consider her entire career span is just 2 years, then yes, probably she has failed.

But if she’s still early in her career, then in my opinion, this is just a setback. Her entrepreneurship journey is not done yet. She can come back again with a new venture and be successful next time.

You could argue that she failed to return investors’ money.

But again, if she had executed with her best effort and intent, then those investors will most likely back her again for her future venture, which could be wildly successful too.

Success and Failure — Dependent

The boundaries between success and failure are diminishing now.

Many times you become successful in future after you face a failure. And many times you fail in future because success goes too much in your head.

Success and failure are pretty much dependent on each other.

If you failed to achieve your desired objective, but keep the right attitude and rise up again, the chances are you have more drive and are better prepared to achieve it this time around than the first time.

In that founder’s case, if she keeps the positive mindset, and decide to start her next venture — (it need not be immediate as she could take a job somewhere and learn more skills as well), then a combination of her on-job training and her lessons learned from previous failure, she would be much better prepared for the next venture.

Similarly, as we’ve also seen in many cases for celebrity people, if you achieve too much success too early, chances are you will lose it all if the success goes too much in your head as with the success, your behavior, priorities, and expectations change.

I just saw this tweet from Alok Kejriwal on my Twitter timeline today morning — it’s very relevant and consistent to the point I’m making here –

Success and Failure — Tangled

On the other hand, we classify “failure” as if everything was lost and there was nothing to gain.

Failure can be absolutely devastating if you look at it from only one perspective.

But if you look at your journey to achieve any objective and the number of other things you gained before you failed in achieving your core objective, you will realize that it’s not a zero-sum game.

In that founder’s case, I could argue that while she failed in her core objective, she had achieved success in other areas like — learning lots of new personal and professional skills, building strong relationships and network, etc.

I’m not saying that we should take pride in failing and nonetheless celebrate it because we learned something.

In fact, I argue that you could be considered failure too from one’s perspective while you’re wildly successful from many’s perspectives.

I’ve known some people who’ve achieved great financial success, but at the cost of some health issues, family problems or some kind of personal sacrifice.

In that founder’s case, I could also argue that there are actually thousands of other people of her age who took more stable, less risky, high paid salaried career paths. So financially they are successful, but from one perspective, they could be considered as a failure too because they didn’t take the risky route she took and didn’t gain those valuable skills and relationships, etc.

Conclusion

So the best way is for us to confront these failures as much as possible early in our life as we do successes too.

And we should treat these failures as more of temporary setbacks in our journey than calling it an end.


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