From Average to Not-So Average

Outside of a few close friends and family, I have never really shared my journey from growing up as an average kid who had zero opinions about what he wanted to be when he grows up and meandered through most of his first twenty years thinking he wouldn’t amount to anything to a decently successful executive who now thinks he can make a positive dent in the universe. This is definitely not a humble brag post, but rather me doing the 5-whys on my own transformative journey and sharing some of my insights with the hope that it might inspire others who might think they are mediocre to go from average to not-so average.

I am not sure how it is right now, but being an average kid in a middle-class South Indian household is not for the faint of heart. Constant scarcity is a bitch and the parents pushed their kids hard into a path that they thought led to prosperity. Growing up, I only had two choices. Become a doctor or an engineer. In all my time as a kid, I was never asked what I wanted to be when I grew up, and after some time, I just stopped thinking about it. I just did what my parents asked me to. I went to all the extra-curricular activities they signed me up for. I let them move me to different schools without throwing a fit. I went to all the extra tuition classes they signed me up for. In the end, it didn’t change a thing. I was an average kid through and through. The only thing I was good at was languages. I loved (and still do!) reading and writing. In hindsight, maybe I should have been more vocal about what I wanted to do. This is something I am acutely aware of as a parent myself. Instead of vicariously living through him, we encourage him to try out different things and push him to double down on the things that stick. We also let him fail and not yell at him for not being good at something that WE thought he might be good at.

My parents always thought I was special. I was. Just not in the way they thought.

Even though I was average, I wasn’t terrible. I scored just enough to graduate high school and a decent enough score to make it to an average engineering college. However, once I graduated, I decided that I needed to leave India if I truly wanted to find my path. I scored decently (average again!) in the various entrance exams that US colleges needed, and I made my way to the States along with a few of my friends. I landed at Wayne State University in Detroit!

When I mention to people I got my Master's degree from Detroit, their immediate question is, “Whoa, Detroit?? Of all the places in the United States, why Detroit???”. The reality is, I didn’t think too hard about where I wanted to go. All I wanted to do was get out of India so that I can clear my head, and I went to the first University that said yes to me. If memory serves right, I believe I also got into some master’s program in Colorado, but it was more expensive than Detroit.

Detroit is a difficult place to survive, and I give the city and its people a lot of credit for reshaping my worldview. Working minimum wage jobs alongside struggling families who were working multiple jobs made me humble and activated my survival skills. If a mother and father in their mid-thirties, working minimum wage jobs with two young kids can make life work, I could do it too.

I had enough money to survive a semester and a half at Wayne State, but I had made up my mind that I wouldn’t ask my parents for any help, because doing so would mean giving up my freedom. I wasn’t smart enough to become a research or teaching assistant or earn a scholarship, so I flipped burgers at McDonald's and maxed out my credit cards. I am pretty sure my family was embarrassed of me, but I didn’t let any of that affect me. The only thing that mattered to me was that I am in control of my destiny. I now believe that people (especially young ones) need to experience some hardship in life.

Hardships activate your survival and adaptability skills.

I would not exchange my time in Detroit for anything in the world.

When I graduated from the Master’s program, the job market was completely dead. It was 2003/2004, and the world was still recovering from 9/11 and the dot-com bust. Many friends moved back home due to the lack of jobs. I was determined to make it work because I had no interest in returning home. I joined a small consulting firm that placed me in Wisconsin, working for an insurance company to do some Java work, from which I was promptly fired. There is something sobering about being let go for incompetence. This was the first time my ego was activated. I decided that I wouldn’t grovel or badmouth the boss who fired me, but instead figure out how to succeed in my next role. I found another consulting gig, but this time I hit the books. I spent hours reading the existing codebase. I didn’t turn down any tasks and met all my deadlines. What I realized about myself was that when sufficiently motivated (which I was after getting fired!), I was a quick learner and even quicker at producing results. I wasn’t the smartest software professional in the room, but I could outperform everyone because I took the fastest path to completing tasks, and to my surprise and delight, that’s what companies wanted

This is where I learned that producing results will always surpass academic purity or perceived smartness in corporate America.

So, with my ego fully activated and with my knowledge of how to succeed as a developer in tech, I set out to climb that ladder and climb I did. I made it all the way to Software Architect, which in current times equates to a Staff/Principal engineer. Being a software architect is 90% cat herding and 10% coding. My boss back then helped me understand that I am pretty good at building interpersonal relationships and convincing large groups of stubborn people to do something they don’t want to do. However, I also realized that there isn’t much of a ladder to climb after software architect. As an immigrant who grew up in scarcity, I wasn’t ready to just accept the fact that I might have hit my career and compensation ceiling. So I decided to pivot to management.

Switching to management was extremely challenging. Keep in mind this was right after the 2009 recession when no one was hiring, and those who were needed experienced managers. No one was willing to hire me. I cold-emailed countless hiring managers. Although most of these attempts were unsuccessful, I established some valuable relationships with leaders I still keep in touch with. I determined that the best strategy was to move laterally, which didn’t grant me the engineering manager title but offered me valuable experience. I navigated through various companies while on a work visa.

Moving jobs while on a work visa is challenging. Your visa isn't transferable, so the hiring company must apply for your visa from scratch, and it costs them thousands of dollars. Additionally, each time you change companies, you lose your position in the green card (permanent residency) line. I believe all my lateral moves likely delayed my green card by about 5 to 7 years. However, I have zero regrets. Each of those lateral moves provided the right experiences and led me to my first engineering manager job, where a supportive boss gave me my chance. Jeff R, if you’re reading this, thank you! Those lateral moves helped me save about 5 years on my journey to an executive role.

Don’t hesitate to take risks and make some lateral moves if it will eventually lead you to what you are looking for.

It's worth mentioning that I was able to make these moves because of my support system, especially my amazing wife, who stood by me through it all. With the right support system, you can realize even your wildest dreams.

As I began managing teams, I realized that I couldn’t depend solely on my ego and my own methods of getting things done to make my team productive and cohesive. I can’t simply do all the work myself for my team, although in the early days, I did that quite a bit and frustrated my team to no end. I needed to change. I needed to learn new skills. I thought about pursuing an MBA, but ultimately determined that it was too expensive and I probably wouldn’t be a model student, given my history with academic success, lol.

One thing above all helped me become a good manager: books. I have always been a fast and voracious reader, which enabled me to absorb a lot of information in a short amount of time.

Books are not the only way to learn something new, but I have found that a well-written book, nine times out of ten, has been more useful than online posts or social media sound bites. So, if you want to learn something quickly, grab a book.

The books that dramatically shaped my management style are :

1. How to Win Friends and Influence People - How to build relationships.

2. One Minute Manager - How to be an effective manager

3. The Effective Executive - How to operate like an executive (I guess I was thinking about the future :) )

4. First Break All the Rules - Management frameworks for the post-industrial era

5. Drive - How to motivate people

6. Turn the Ship Around - How to convert task followers into problem solving leaders

I also read an HBR article in which the writer argued that managers need to be more vulnerable with their teams, which encourages employees to open up. The writer also said that managers should own up to their mistakes, which encourages employees to be self-critical. It was complete serendipity that I came across that article, but that single article impacted me tremendously and has definitely shaped me into who I am.

Be vulnerable, transparent, admit to your mistakes, and learn how to apologize. When done consistently, your team will do the same. Teams have a funny way of reflecting back what you give them.

My ‘graduation’ from engineering management was my time at Amazon. If you have the option to go to Amazon or pursue an MBA, choose Amazon. Amazon’s culture (which isn’t for the faint of heart) will transform specialist leaders (engineering leaders, product leaders, etc.) into business leaders. This is where I learned how a technology business actually operates. I learned everything from assessing the size of the opportunity to determining the TAM (total addressable market) for a feature or product, how to align stakeholders, how to execute through a team, and how to launch it in the market. I also got promoted and began managing other managers. Things were good. So good that I decided to pivot.

My friends told me I was crazy to leave such a great job. They weren’t wrong, but I also had zero interest in slogging at a company for a decade plus and hope to become an executive or a senior leader. Also, Alexa had grown from just a thousand people when I joined to close to ten thousand people in just three years and had become a giant bureaucratic machine. I wanted a faster path to the C-Suite. That’s when Smartsheet came along.

Smartsheet was a relatively unknown company in 2017. They were looking to hire an engineering leader who could build out an east coast development hub for them. I interviewed with them and I got the job. The next few years was a ride of a lifetime. The company IPO’d a few months after I joined and its growth took off. I was able to build all the high value leadership skills that I needed to break into the C-Suite in an extremely condensed time frame. Skills like:

1. Recruiting at scale. By the time I left, my org was north of a hundred people across multiple geographic locations.

2. Help define and enforce company culture

3. Helping set department level goals, including figuring out input and output goals.

4. I learned from top executives. My bosses gave me immense responsibilities and freedom, including allowing me to run both product and engineering!

It was a challenging job, but I enjoyed it and was fairly successful at delivering value through a tightly-knit team that I built from scratch. If I had to highlight a few things I did that contributed to my success there, they would be: a) Building relationships with key leaders, stakeholders, and customers, b) Never starting with a ‘No', c) Encouraging bottom-up thinking, d) Learning how to hire good leaders.

Eventually I got promoted to VP and……Covid happened.

After spending more than a year under lockdown, we (my wife and I) decided to get out of snowy Massachusetts and move to sunny California. I started looking for CTO gigs in Southern California and got randomly connected to Kajabi through a common connection. I interviewed there and got the job to run engineering. This is where I fell in love with the creator economy, which eventually led me to Everette and Kickstarter, where I currently am the Chief Product and Technology Officer running both product and engineering.

I am rapidly hurtling towards the end of the career arc I am on right now. I am not sure what the future looks like, but I hope it involves a lot of writing, teaching, and helping. I am on a mission to send the ladder down to others who are were I was five or ten years ago. All you have to do is ask. Readers, if you want my advice on anything, start here https://intro.co/MaheshGuruswamy.

P.S - For new readers, If you are a manager and are struggling to deliver bad news, my latest book will help. Get it here https://www.amazon.com/How-Deliver-Bad-News-Away/dp/B0D7FHTTNN

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