How I view building my career: a forward-looking decision framework

When I have career chats with people, I seek to understand the reasoning behind the big decisions in their career path. I am curious to learn how other people chose between role A and role B, or why they prefer to grow as a people manager vs. an individual contributor (IC), so that I can take away generalized logic to build my own career.

Here, I will discuss some decision making frameworks on career building that I’ve encountered, as well as my own. While most of my other articles on the subject usually focus on what I have concretely accomplished, this article is more future facing, and focuses on the thought process, rather than how the results might be in a few years.

One: Real experience of 5 years, not 1 year experience repeated 5 years over

I believe that careers can be built intentionally. It is fully within one’s control to develop new and interesting skills at work. The opposite extreme is the following scenario, which I am deathly afraid of:

There are many ways of measuring experience, the most popular being tenure. However, working in the same place for five years does not imply five years of experience. If you’ve been doing exactly the same thing, day in and day out for five years, and it only took a day to learn, you have one day’s experience, five years over. - Jacob Lund Fisker

In my career I value learning, expertise, and variety. This is not a selfish wish - it can easily be achieved in harmony with organizational needs. I provide value to the organization with existing skills that I bring at the time of hiring; it’s also in any organization’s best interests for their employees to constantly be pushing the boundaries of their skills. The org even gets much more bang for buck this way.

For my first data science role switch, I was looking for variety, which I felt was a way to avoid repeating my experience too much. I conceptualized variety as two axes: industry and company type. I managed to make a move on both: from telecom to fintech, and from large enterprise to a ~200 people startup.

What I learned from a large enterprise - many-in-one bundle deal

When I was in a large enterprise, I felt that my main takeaway was how scale works. Any data science project I worked on would have a vast amount of data at my disposal, and impact millions of users without much effort on my part on the “acquisition”. For a smaller company still growing their customer base, this would be a luxury.

On the business side, I got incredible insight into “how Canada works”, and would never trade this experience for anything. Because of this, I actually recommend every professional to work in a large enterprise at least once in their life. To illustrate how it’s like a many-in-one bundle deal:

“Robelus” are Rogers, Bell, and Telus. While it feels like there is competition in the telecommunications space in Canada (sarcasm), there actually isn’t - each of them own multiple other telecoms, respectively, in the premium, affordable mid-price, and pre-paid low-price consumer markets. For readers in the US: It’s like how T-Mobile owns Sprint.

I also gained an insider look into industries such as media and supply chain: Bell Media owns Crave (subscription streaming platform), CTV and several news channels, and The Source (electronics retail, originally Canadian RadioShack). Bell and Rogers co-own MLSE which owns the Toronto Raptors (NBA team), Toronto Maple Leafs (NHL team). It was really a many-in-one deal, in terms of career experience for me.

All this to say: If I went from a large enterprise to another large enterprise in the same industry, I couldn’t learn exponentially in the same way. I wouldn’t be surprised again by how large departments and teams work together. Hence, the next step was ideally on the other end of the axis, such as a startup.

I think I made the correct choice - and I’ll probably write a follow up article once I’ve learned more from Fintech, venture capital, and ecommerce.

Two: Big fish in a small pond, or small fish in a big pond?

If you’re the smartest person in the room, you’re in the wrong room.

I agree with this saying to some extent: it comes down to the marginal benefit of learning at the stage of one’s career. I imagine that being a small fish in a large pond is much more beneficial early career, and then in mid to late career, being the big fish in a small pond, so that one can pass on the knowledge to others.

Being the “smartest person” in the room early career, is possibly the easiest way to make one’s career plateau. A local maxima would be an apt analogy. But even if it’s not the right time to leave for another opportunity, one can still learn from the outside world.

In software, working with open source is a great way to understand best practices and collaboration with incredibly talented people, not limited to one’s full-time “small pond”. I personally have learned a lot just from tinkering and making small pull requests. I suggest reading Let’s do some open source if this is a new concept to you.

Back to career decisions: I try to be aware of possible stagnation, and reflect regularly if this is happening. I want to avoid being like the fable of a frog in boiling water, which isn’t aware of its impeding demise until it’s too late.

Three: Proactively learn from intentionally built career paths

Here is an example of two career chats, with real life details changed. Both people were directors or leads:

  1. Worked in a large enterprise for ~10 years, was laid off, and then went to another large enterprise in the same field.
  2. Worked in different fields and varying company size.

Both are people that accomplished a lot in their professional lives, but 2’s trajectory was much more self-designed, and I believe 2 has much more experience, compared to 1 which could plateau at 5 years of experience repeated 3 times (see quote above from Jacob Lund Fisker). In addition, while 1 did complete many projects, it seemed like a function of time, rather than deliberate choice.

When asked, only 2 could answer why they made each career decision, which was immensely helpful, because it is something I could model myself. Meanwhile, 1’s advice boiled down to “just stay put, find the next job when the universe grants it, and find a new learning experience when it falls into your lap.” Because 1’s advice is unreproducible, it’s simply something I keep in mind as a personal “do not do”.

There are some resources I recommend to read about people’s career paths, in order to pick out reproducible patterns that I can apply to my own unique situation:


I feel that since we are all alive on this world just once, I’d rather proactively seek out growth, rather than just let life happen to me until I die. I understand some folks may value other things like family, and thus decide to only build their careers in ways that are offered to them by “natural” circumstance. I respect that; I also value many things outside of work.

But personally, since we are working 40 hours a week or so, that is a huge part of life. No matter how much quality time in the evenings or weekends I spend on other priorities, I would still be wasting my life if I didn’t grow and get satisfaction in those 40 hours a week. This is why I think about how to build my career intentionally and not accidentally.

These thoughts on career are still being updated - I imagine that I will have more revelations on what works and what doesn’t work, as time goes by. As usual, feel free to reach out on LinkedIn or about this article.

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