10 min. read

April 21, 2020

career development

The Hidden Powers in Admitting “I Don’t Know”

This is a story about failure, vulnerability, and imperfectionism, and how to use all three on your journey towards self-mastery.

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Randy Tolentino, Software Developer | Team Lead

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The look on my face when I have no idea what’s happening…

“Hey, Randy. Did you see the email?”, my manager asked in a direct message. “Mmm, I did not.” “No worries, I can catch you up. We just got off the phone with a client who reported their entire site was down. They asked if you made any updates this morning.” “I don’t think it’s anything I did.” “Cool, just checking”, he followed.

I was in complete disbelief — I had just lied to my manager and I couldn’t figure out why I typed those words and hit send. I sat at my desk in a state of paralysis, thinking to myself, could that have actually broken their site?… there’s just no way. My hands started to shake from being nervous, and my heart sank as I slowly unfolded the gravity of the situation.

The truth was that I actually had been in the client’s production instance, trying out several plugins which would help solve one of their own requests. But in the moment, I wholeheartedly believed that nothing I was testing could have brought their site down.

I messaged my wife and explained how I just made a major mistake at work, and how I dug myself into a deeper hole by denying any involvement with the site crashing. I also told her that it wasn’t just some ordinary client website, but that this particular organization receives hundreds of thousands of site visits per day. She tried to de-escalate my anxiety, but I was past the point of being helped.

I was having a breakdown and it was only 9 AM.

“I need to take a walk,’’ I told her. Then I zipped up my coat, threw on my beanie, and exited the office building within seconds. As soon as I stepped outside, I began to shiver uncontrollably, unable to distinguish if it was from feeling anxious or the 40 degree Fahrenheit temperature that morning. But I walked anyway, because in my mind, I deserved the punishment from the cold.

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A well-deserved walk in the cold…

After one circle around the block, I returned to my desk to confess what really happened, knowing that the problem was two-fold. My wife encouraged me to just say it was a mistake, and to be as honest as possible with my manager until the whole thing cleared. She was right. I opened my direct message with my manager, took a deep breath, then began to type.

“Hey Alan,” I sent, “I owe you an apology. I actually was working on the site earlier before anyone got in, I don’t know why I denied it, that was completely out of character. I’m sorry for that.” “That’s okay, Randy. I’m going to book a room so we can get together and figure out what’s going on with their server.” “Thank you. Again, I’m sorry about all this,” I said as I fought the urge to cry.

By the time we got into the room, we received a follow up call from the client who informed us that they had figured out the issue and already solved it by simply restarting their server. Great, I thought. With the client’s website problem out of the way, all that was left to figure out was the dishonesty piece.

We sat and talked it over for a few minutes, then decided to move on with our day, though for me, it was already too late, my day had been ruined. You did this to yourself, you know. I needed to step away from work completely and take a few hours to get it together, mentally and emotionally. I requested for a last minute day off, and it was immediately approved — they knew I needed it. So I quietly packed my stuff, and messaged my wife that I was on my way home.

I was certain that by the following day, I’d be out of a job.

Residual effects

Fortunately, my manager had accepted my apology. The next day, during a quick check-in, I realised that he had forgiven me, and also gave me the benefit of the doubt since he felt that I didn’t break the client’s server after all.

Over time, he continued to show support for my work, though he knew my confidence was shaken. In the subsequent weeks following that disastrous trail of events, it felt like my work was built on thin ice. All of a sudden, every task seemed fragile and even the most basic code assignments had me feeling uncertain. I was slower to deliver work, I second guessed my ability to problem solve, and probably the biggest problem of all, I stopped reaching out for assistance when I needed it.

Eventually things would return to normalcy, although it’d be inaccurate to pretend that I didn’t struggle with some of the residual effects of that morning. About half a year later, I decided that I was ready to pursue a new role, a decision which mainly stemmed from wanting to level-up my skills from a technical perspective. Deep down though, I knew that in order for me to really grow, I would have to address a significant, internal blocker: I was scared of being exposed as someone who doesn’t know what he’s doing.

Let’s call it what it was: fear.

Interestingly, that fear would play a transformative role in my mindset for my upcoming job search.

Leveraging weakness

Just to provide some context, interviewing for a software developer role is a scary thing. These technical interviews involve the infamous white-boarding or live coding exercises, framed around complex algorithms, which, many times have nothing to do with the day-to-day expectations in the role. These can be extremely difficult for people like myself who don’t have the traditional computer science academic background.

Quick aside: prior to working in the tech industry, I had never heard of the term imposter syndrome — not in college, nor during high school, and definitely not in elementary. But once I learned more about the phenomena and had a solid understanding of what it involved, I had a stream of connect-the-dot-in-hindsight moments where I had definitely experienced feeling like an imposter (even all the way back to elementary).

In the beginning of my search for a new role, I had a life-changing aha moment. Instead of dreading the technical part of interviews, I needed to:

  • give myself permission to fail

  • allow myself to be vulnerable

  • learn to accept times when I didn’t have an answer.

This realisation was empowering and I had faith that these upcoming rounds of applications and interviews were going to be the perfect opportunity for me to experiment with failure and submerge myself in discomfort. I knew I would fail at some point and I knew I would run into scenarios where I would be exposed.

I was hyped, and I found myself on the other side of my internalised fears. At this point, I was looking forward to failing.

Experimenting with vulnerability

‘You have an amazing wife who loves you, with two brilliant sons. We have each other. Life is great.’

Those were the reassuring thoughts that I would replay in my mind over and over as I headed into my interviews. They provided me strength and protection as I prepared to face my worst (professional) enemies: fear and imposter syndrome.

Rehearsing these affirmations and actually believing in them let me know that if everything goes wrong today in this interview, you still have a great life.

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Technical whiteboard exercises

My first onsite interview was an all day event for a company in the healthcare space. The agenda consisted of 6 separate “conversations” with various people in the company. The first technical exercise was a white-boarding activity and its algorithm was unlike anything I studied for. It was so complex that I can’t even articulate the problem to this day. But (and this is an important but), it served its purpose in the bigger picture. This particular whiteboard problem had me feeling uncomfortable, it allowed me to fail, and it gave me the opportunity to recenter myself on those foundational, reassuring thoughts from above.

Later that afternoon, they passed on my candidacy.

A few weeks later, I attended a different onsite for a company in the financial space. Interestingly, by the time I stepped into the technical interview, I felt a little more relaxed. Wait, was the experiment working already? I was presented with one algorithm question which I had several solutions for, and another whiteboard activity which I was also able to answer. There were a handful of questions that I didn’t have an answer for, but I was at peace.

On my way home from this second onsite, again, I revisited my reassuring thoughts and embraced my truth, I have a wonderful family… life is great, no matter what.

Days later, the same thing — I found out that I didn’t get the role.

By the time I interviewed with a third company, I felt that I had made a lot of noticeable progress in my attitude towards not having the answers. I felt no shame, and I wasn’t embarrassed to admit “I don’t know”. I felt secure enough to fail, knowing that everything was going to be alright.

During this interview round, I found that I was able to carry myself with more confidence than ever; I could articulate ideas more clearly, I was comfortable, and I didn’t panic in the moments when I came across a question or topic I was unfamiliar with. At the end of the day, even though I felt great about the interviews, I still recited to myself as I left the building: I have a beautiful family, my wife is the best, and I’m blessed to have my boys…

It could be a coincidence, but I accepted an offer with the third company. I did it. By addressing my fears of not knowing and by also being okay with the possibility of failing, I unlocked new opportunities for myself to grow.

Life is great.

This can work for you

I don’t think this journey was for me, alone, which is why I’m sharing this with my extended network of family members, friends, and colleagues. As human beings, we’re constantly working through mistakes and continuously finding ourselves. Maybe you have your own internal fears or self-perceived insufficiencies to overcome — I believe we all do. I also feel there’s no better time to consider addressing these things than now, as we finish out the last pages of this decade and start a new book in 2020.

If you’re like me and potentially millions of others who are currently invested in self-mastery, I encourage you to consider trying the following thought experiments and ideas:

  1. Continuous learning

    Adopting this mindset automatically places you on a track where you’re free to always be in a state of discovery. Free yourself from feeling like you have to know everything, today, in this moment, and all the time. Instead, you’re continuously learning and constantly improving, and therefore, it’s okay to not know.

  2. Use reassuring truths as your foundation

    Ground yourself in your truth, whatever that may be. Your friends love you, your family is safe and healthy, you have skills that companies need, etc. Remember the bigger picture and proactively remind yourself of this no matter how you perform in different scenarios.

  3. Fail safely until you get used to it

    Failure is a sensitive area that many of us desperately try to avoid, but there’s a way to fail without letting it hurt your life. Embrace the imperfectionist in you, the one who’s allowed to fail for the sake of learning. Surround yourself with people who share a similar mindset. Accept you for who you are, and get into the rhythm of asking for help — all these practices help make it okay to fail.

  4. Learn to identify the lessons

    If you fail the right way, you’ll find a wealth of hidden lessons, somewhere buried in that journey. Learn to unearth those gems and you’ll gain more knowledge, acquire new skills, and you’ll have a more positive outlook in general.

  5. Share your stories

    The more we inform each other of our fears, failures, and triumphs, the more we learn as a collective people. I encourage you to let these moments and experiences find their way into the world so that we can support and inspire one another.

I still don’t know

To this day, I still find myself in situations where I don’t know. This happens every day, especially due to the complex nature of my role, but I’m positive that this is not specific to the tech industry. However, nowadays it doesn’t include the negative impact on my self-worth like it once did. Instead, I interpret these moments as signals that are designed to light the path towards discovering something new.

It’s fascinating when we examine how these understandings can improve our mental well-being — navigating failure to find success, and utilising fear to ultimately find security.

I’m here to tell you that the next time you encounter a problem, a task, or a situation where you don’t have an immediate solution, you’re going to be okay. What gives you the right to be okay with not knowing? You’re human, you’re imperfect — you just have to believe in your ability to learn.

In the year 2020, we’re moving towards better versions of ourselves. Be excited because I’m looking forward to hearing your stories of personal growth. I promise that when you give yourself permission to fail the right way or ask for help when you need it, without shame, you’ll find yourself in a better place, every time, this I know for sure.

Now, in terms of where all this will take you, I’ll have to be completely honest… I don’t know.


This piece was originally published on The Start Up by Medium. You can find it here.