JT9 | Prasad Naik On Taking A Career Gamble

Discussion Topics: Prasad Naik on Taking A Career Gamble

• The key decision-making points were role, compensation, career growth, and location.
• Making a pros and cons list did not work as it felt too static.Prasad decided instead to draw a decision tree of his choices till date so he could better introspect on what drives him, which ultimately led him to a key realisation and hence his eventual choice

His advice:

• Realise that your objectives will be different at different life stages
• Look at your past decisions and levels of success/ satisfaction to understand what drives you and hence define your objectives
• Ensure the immediate next step fulfils them, while also setting up a long-term and exciting future
• And where possible always try to acquire a broader perspective to make even better decisions

Transcript: Prasad Naik on Taking A Career Gamble

Hi welcome to JobTok, have you ever had to make a choice between a safe role that you know well, which will keep you moving forward. Versus something new and different and unknown that could really accelerate your career. But equally it could turn out to be a dead end or even a career disaster. Do you take the safe, boring route to the top or do you roll the dice and take four, might be the biggest gamble of your career.

How do you choose? Today we talked to Prasad about exactly that kind of choice and how he made the decision between a safe, lucrative job offer with a leading global brand versus joining an upstart on its growth journey. So, thanks so much for joining us today. We are keen to hear about your experiences, but first, would you like to tell us a bit about yourself?

Sure. Thanks for having me. Hello to the listeners. So I’m Prasad, I’m the Global Head of Support at a company called Wolt. This is a fast-growing delivery platform based in Helsinki, Finland. And we’re currently operational and. In 23 markets, including Germany and Japan. And I joined about a year and a half ago.

So support is a top competitive differentiator at Wolt. And my goal is to ensure that we can scale our operations without diluting what makes us special. And this is not so easy. given that we grew our headcount by a factor of 5 in the last year to 2000 people. And we have to manage all these issues such as COVID, IPO preparations, regulations, GDPR, et cetera. And previously I worked at UberEATS in regional operations in EMEA, Customer Success at Grabfood, and also at Uber. And that’s where we met, Amit. And previous to that, I actually did my MBA at Cambridge.

And before that, I used to work in Investment Banking in the UK. And I’m currently loving my role at Wolt because of how much I’m learning every day, challenging myself. But joining Wolt wasn’t a very easy decision at all. Yeah, it was a big gamble and that is what we are going to be talking about today.

Yeah, I remember actually, when we first talked about this role. I think it was around two years ago, right? Pretty much around this time of the year.

Yeah, it was about two years ago. And if I remember I was in a bit of a stupor trying to figure out what to do. I called you because you are the last manager that I really worked with, that I felt a good connection, and who could really advise me on the next steps. And yeah, basically I found myself in a job that was a dead end as far as I was concerned, you know

I was working at Uber in Amsterdam as part of the EMEA central team. And, all of a sudden the org structure and management changes. I find myself in a role that was very different from what I signed up for. I wasn’t learning anything. I was working on these low-impact projects. I didn’t have the creativity that I desired. Or the flexibility to choose my own projects. And I was basically stuck in a rut.

And I was therefore open to new opportunities and, long story short, I ended up applying for, and I’m getting two offers. So one role was to relocate back to Singapore and work at Facebook and an APAC-wide team focused on regional operations for their sales teams.

And the other was to relocate to Helsinki and actually build out a central team for support at Wolt for all our global market. Two quite different roles.

Okay, so Prasad, just to be clear, the choices you had were to stay at a truly world-changing unicorn or join what is one of the most sought-after companies in the world or move to a growth-stage startup. I bleed for you, the hardship seriously!

It’s a first-world problem. Haha

Yeah, but seriously though, I think most people would kill to have any one of these options. So you were really lucky to have so many, but again because these are all great opportunities, it must really have been a tough choice. So what was going through your mind?

Yeah. And not to sound ungrateful, but this is quite a big choice because  I have to think about your family and other things. So. It was easily one of the hardest decisions I ever made, you know there were three outcomes, basically, right? I would stay at Uber or I would join Wolt or I would join Facebook and there were so many issues to consider, it was quite overwhelming. It was almost like being paralysed by this decision.

I reached out to you. I might, as I mentioned before but at the end of the day only you and your gut feeling can make that decision. And, there were a few things to consider, right? So the first was the role itself. Would I be good at the role that I enjoy making an impact based on my experience at Uber currently in Amsterdam, I wanted to make sure the next job I did that I really enjoyed it.

And I could challenge myself. So with Facebook, I was confident that I would do a good job. It was what I did before at Uber. However, I wasn’t sure that I would necessarily be so happy in the role because I wouldn’t learn much. The role at Wolt was definitely a higher impact role as I would be the Director of Support and therefore define and project manage the strategy for 23 countries. I had a broad idea of what I would work on, but if you live in such a large central team it would be quite diverse. And it was a real gamble. I mean, what if I was over my head? What if I get fired? How would it look on my CV?

There was a lot of this imposter syndrome kind of thinking. And I never had such a big responsibility before and so much autonomy and visibility. So what’s that ready for it? All I knew is that Wolt was riskier. But it also had a bigger reward in terms of learning and ownership.

The next big factor was creating a trajectory. Now, where would I be in five years? And this was more clear Wolt was definitely the better opportunity.

However, Facebook is also a household name. So it would always be a good look at the CV. But I was aware that I’d be joining a team of five others at the same level. And so there’s a risk that I would remain stagnant and how quickly would my career progress? My age was an important factor here. I was thirty-three at the time.

I spent my twenties in another career path in banking. So I was acutely aware that by joining Facebook, I could end up being lost in the grand scale of it all. And it’s that old analogy, right? Like, do you want to be the small fish in the big pond or the big fish in the relatively smaller pond?

And another major factor was compensation. I mean, just to be realistic about it, you know? It’s a very important factor. Facebook obviously pays very well. And when you take into account tax rates in Singapore, You could have quite a comfortable and easy life. Wolt also on the other hand made a very good offer, but that was a gamble as, as with a startup you have a lot of it geared towards stock options and based on my risk with Uber It kind of gave me a bit of PTSD.

And the final factor was relocation. I lived in Singapore before and I loved it. My wife and I had a great time there. The weather, the food, the people, travel opportunities, Bali where my wife and I want to end up in. And also we were planning to have a kid, so I would have loved to have them go to school in Singapore. Helsinki on the other hand was a major, major, negative. I left the UK for Singapore to avoid the weather and Helsinki makes the UK look like Singapore. The food is really bad and the cost of living is super high and the taxes are quite insane.

I know I’m really selling Finland here. But actually, with hindsight, I was quite wrong. A lot of that. It is a great place for families, but anyway, when making the decision I was irrationally obsessed with Singapore and getting my hands on chili crab and durians again.

So anyway, there were positives and negatives of both and if I had been able to get Wolt in Singapore and that would have been an easy choice, but I couldn’t. So I have to make a choice between these two and guide the next five years of my life, at least.

Yeah, actually, that’s true. I realise a lot of folks tend to move around frequently, and that’s okay if it works for them. But a lot of career growth actually comes from sticking around. Building credibility and being there for the big opportunities when they come along. So, yes, I think you were right to think about this as a longer-term decision, rather than just something to try out. Plus, of course, you had to relocate. Which made this a bigger deal than it would have been if you just stayed in Singapore. So, how did you actually think it through?

Yeah. So as you can see, it looks like a large diatribe in my head of all these different factors. So classically what you do is you write these things down in a for and against the column and you try and figure it out. However, I didn’t find this very useful. It was too static. I needed to understand how this decision relates to my past choices and how it relates to my future and where I want to end up. So I actually ended up thinking of my career as a decision tree.

If you look at your career history, you can visualise it as a series of choices you have made, right? Whether it’s taking on internships or courses or projects or relocations joining another company or RO.

And as you make these choices, the future decision tree will unravel to give you a new set of permutations and new branches, et cetera. As you walk through this past, you know and make decisions at a particular node of that decision tree. You tend to make that rationally or irrationally based on the knowledge, principles, goals, and circumstances you have at that point in your life.

So I tried to make sense of these historical choices from that perspective. What choices did I make that were good in the past and what information was it based on and what were the bad choices that were made that I needed to learn from? And you could obviously post-rationalise here, but it’s worth being really honest about what actually happened on your journey at that point in time, as you made those choices.

Hmm. Actually, this is a really interesting way to think about things. So, essentially not just a forward-looking list of pros and cons, but actually as, almost like a backward-looking reflection on choices and how they worked out. So you can avoid making obviously poor choices as you go forward.

Yeah. And just to go through the example of my early career choices. My only goal initially was to earn a big fat salary after graduation. I wasn’t concerned about job satisfaction or some big hippy goal of helping society. It was a very basic decision tree with a lot of blind spots. How do I get more money? And I was quite shocked when I remembered my thinking back then.

Banking is what everyone of my colleagues and friends was doing. They look like they have Rolexes. Okay, great. Let’s do that. So it didn’t really matter that I was working 90 hours a week and hating my life dealing with the doom-listening of Radiohead and the Smiths. It was just let’s move along this path until it gets better. But it didn’t get better. I really hated it. I wasn’t very successful over time as I didn’t care. And I eventually burnt out.

And given my blanket decision-making I was stuck on this decision tree branch of banking. And I didn’t see how to traverse to a different branch of the tree. I needed to go back a few steps of this decision tree. And given my limited options and knowledge of what I wanted to do or could do, seeing only part of this decision tree, I eventually ended up deciding to do an MBA. I needed some breathing room and it was actually the best decision I ever made as I was able to take multiple internships in multiple sectors.

I was able to benchmark myself against others. And it brought me knowledge of alternative career paths on this decision tree. It gave me the confidence to try it out. But also it opened the doors to those paths because of the Cambridge name.

So sometimes it’s actually worth going back and expanding your horizons and trying these other paths. And I eventually joined Uber in Singapore with you, Amit, in your team when I was given a lot of freedom to drive these big changes that led to a lot of success.

But then I made a couple of mistakes, honestly by rejoining Grab, after they acquired Uber’s operations. In that role, I felt I didn’t have that much autonomy to drive change. And then I joined Uber in Amsterdam and that’s where the story begins.

It was basically a realisation that in these roles, I wasn’t interested in doing the same thing every day or driving the small step changes. I’m really interested in these big, big projects. Based on this analysis and I realised, yes, the safer option was Facebook with this reliable compensation and living in Singapore would also be great. But I knew that I needed to choose the company that offered me the better role. Not just the extraneous stuff, incidental to the road, like compensation or location. And I’m happiest when the job isn’t the means to an end, but the end itself, and I was determined not to make the same mistakes again. And I was happy to take the gamble as the opportunity to take a role like this would not come about very often. And it also allowed me to jump ahead a few steps in my career and open up these new opportunities, given the seniority of the role.

The fact that you did self-reflection at this stage in your career is in itself I think quite impressive. Most people don’t do it even in their forties or fifties or frankly ever. And I know I haven’t actually done this, so this whole conversation is kind of eye-opening for me as well. And I have to say getting self awareness early on is fantastic. And clearly like this process and the knowledge that you’ve gained through it will help you for the rest of your career and probably the rest of your life as well.

But the million dollar question here. So now you’ve made that choice. How did it work out?

Firstly, just to say that this thinking came about because of the huge number of mistakes I made in my twenties. I was pretty much falling down the decision tree rather than climbing up it with any kind of vision. So it kind of just came about organically, but yeah.

And based on this, like thinking it turned out to be the best decision I’ve ever made. I was very proud that I took the risk against the advice of pretty much everyone that I spoke to. I was the only one that wanted to do this actually. And it turned out to be the best option because I love my role. And I made sure that I didn’t make a decision based on these extraneous factors. And at Wolt I don’t really consider it a role. I think of it actually as a passion or a mission without sounding too cheesy. Yes, of course, there are issues with living in Helsinki and my wife hates the cold, but you know there are other things that make up for it. And I look forward to my projects every day. And I actually think about what, what would have happened if I took the other role at Facebook and I’d always have this eye on this opportunity and regret it forever.

Yeah. So I think that honestly looking back, I think it was a good choice.

I know I was one of those people who also suggested that you join Facebook so I have to say I’m very happy that you decided not to take my opinion here. And I think what you just said right now about regretting things forever is a point that will resonate with a lot of people listening in.

We’ve all made choices that we regret. And while it might not be possible to eliminate all regret in life, at least we can minimise them. So, what would you recommend to people worrying about making a tough decision or perhaps moving out of their comfort zone?

Yeah, absolutely. And  I think firstly, I would say that we are all very different people with different objectives and at different stages in life. And these things change and your decision-making criteria change as you go along your own decision path. And my advice to those who are making such great choices is to first understand that variance.

Your decision-making this year would have been different from what you chose last year. Maybe you have family, or maybe have different levels of savings now and so what I would say is to map out your historical decision-making tree and understand why you took those steps. What was rational and irrational?

Did you give yourself enough choices? Was it the role, the money, the location, the prestige, boredom or something else? And be very honest about that. And then evaluate what actually went well with those decision-making criteria. What were the good choices based on and what were the bad based on – then for your future career, you can apply those learnings to it. But the first step is to just be cognisant there is a variance throughout your life.

And second as you look to the future of your decision tree and you unravel it you have to look at both the immediate next step, but also the longer-term career at the end of that tree, what does that end path look like?

And that’s the problem that I had in my early twenties, I was looking at the immediate next step, not necessarily where I would end up in five years. Sure you have that fancy next job with a high pay or a great location. But what about in five years? Can you progress in that role? Will you end up in a dead end? What options will we have at the end of this branch? Can you come back a step and correct it easily?

Also the other way around is important too. If you don’t enjoy your current role and you sacrifice the present for the future, you may not be successful or burnout and never realise that goal in five years time. So you need to have this short and long-term thinking within that decision tree.

And finally, I would advise you to open up your horizons as early on in your career as possible. So if you are in your twenties have that freedom to be able to traverse different paths, try different things, open yourself up to opportunities so you’re not stuck in the one career path that you think is the only option. I know so many colleagues at Uber when we worked together and I met people that came from consulting or other areas. And they realised that they wasted the early part of the career, but then again, it’s part of your journey, right? You need to understand sometimes what you don’t want to do to be able to understand what you do want to do. So take everything in its own merit. And yes, you are post rationalising a bit, but then again, you’d have to learn from your mistakes. And yeah. Earlier in your career it is easier to correct your decisions. So yeah, those are the three things I would say.

Yeah. So thanks a lot. These are all extremely good points. And if I might summarise, essentially, you’re saying:

• First, we need to use our past decisions to honestly understand our motivations. And the keyword here is honest. This is not an interview or a LinkedIn post, I guess. Where you have to look your best. So no point fooling ourselves.
• And then we use that self-awareness to pick something that we will enjoy for the right reasons. And then figure out whether this next step in the journey has a longer-term future or whether it might turn out to be a dead end
• And all of this is made easier if you have a broader perspective, which you can gain by exploring the world outside of the scope of work, as you said. Do an MBA or meet up with people or discuss with people who have different experiences

So I think all of this is extremely valuable. A lot of people face this challenge on a pretty frequent basis. And I think the way that you’ve structured this whole thought process using a decision tree and self-reflection I think is something that any one of us can do, not just early in your career. So, thank you so much for that.

I really appreciate having you with us today. This was eye-opening as I said, and now I’m even inspired to go think of my career and future journey in a whole new way.

So, thanks everyone so much for tuning in.