Career Switching Journal — Part 1

6 min readJun 23, 2022

For those who had come across my articles, it is very obvious that my intention behind the content has always been to help as many people as possible, no matter it is to understand complex technology concepts or to resolve long hauling problems. I have always been the hands-on, deep-dive person, so that part of me will always be there and there will still be cool technical write-ups coming out here and there in the future.

I cannot clearly remember how the idea of switching to another career started. All I can recall is that I needed more and more to motivate myself to work every day. When I look back at my 8-year working journey, the trajectory seems crooked and disorganized, but at the same time with the constant of change.

“Above all, don’t lie to yourself. The man who lies to himself and listens to his own lie comes to a point that he cannot distinguish the truth within him, or around him, and so loses all respect for himself and for others. And having no respect he ceases to love.”
Fyodor Dostoevsky, The Brothers Karamazov

Great. I knew I needed a change, but what? I never had a thinking structure when making big decisions, maybe because of my personality and I never had a lot to consider. With what has been happening in the society nowadays and with my new identities in life, I needed to think more. I needed a way to deal with what all was in my mind and still make progress.

I break down my career-switching journey into 3 phases, which are plan, perform and pivot.


This phase to me is the most important phase of all 3 as it sets the goal and strategies to reach it.

If you stop and take a moment to think, finding a job is just like finding the next restaurant you want to try. The market mechanism is the same, supply and demand. The truth is most job-hunting people know about this, but they often overemphasize the weight on market demand and forget about what they themselves can provide.

I created this flow chart to better demonstrate the thinking process in my head at the time.


There are 2 parts. Essentially, strength and weakness are what I already have, and passion is what I might want to have but am not yet there. In my opinion, it is extremely difficult to know exactly what I want to do. So, instead of beating myself up on thinking deeper on that, I just put down whatever comes into my mind and change anytime in the future when needed. At the end, I wrote down the following.

Personal Strength (PS):

  • Logical
  • Fast learner
  • Strong initiatives
  • Great collaborator
  • Work smart.

Personal Weakness (PW):

  • Get bored easily with the routine.
  • Bad at saying no when needed.
  • Jump to solution quickly when being asked.

Professional Strength (PfS):

  • Customer engagement
  • Cross-team collaboration with tracked records.
  • Cloud technology — Azure IaaS and PaaS
  • Open-source technology — Linux, container, Kubernetes

Professional Weakness (PfW):

  • Had never been on the product side.
  • Little experience in software programming.
  • Little experience on leading programs.
  • Little experience on leading a team more than 5 people.


  • Product management
  • Program ownership
  • Data analysis

One interesting fact I found when I was doing the exercise is that I doubted myself every time after putting something down. It is great to know that we are not alone for having that feeling of self-doubt.

“Our doubts are traitors,
and make us lose the good we oft might win,
by fearing to attempt.”
William Shakespeare, Measure for Measure

Environment Assessment

This process is pretty straightforward as we might already have some ideas even before starting. A few pointers to provide are instead of thinking what companies we want to work for as the first step, we should be thinking what whether the company’s mission statement aligns with what we are looking for and whether the company’s business strategy is toward the areas we are interested. At the end of the day, if we do not look at the big picture, we can be progressing without clear directions and that just potentially leads to more frustration. Let’s take an example. I may want to work in a technology company and I know names such as Google, Adobe and Salesforce. Google is the closest to a traditional information company of all 3. Its strength is the cloud market for consumers and its mission is “to organize the world’s information and make it universally accessible and useful.” Meanwhile, Adobe and Salesforce’s strength are elsewhere and having different business goals in mind. If we take a step back to look at what is going on and what will be coming in the company or even in the industry, we might have a totally different perspective.

With the industry and company research done, the next step will be looking for open positions in each respective company but that will require the self-assessment result.


I will like to tell you the hardest part has passed but that is a lie. What we have gone through is barely the prerequisite. The rest of the planning phase is all logical and methodical. In most company’s job openings, the description will include at least 2 parts, what the position is doing on a day to day basis and what the required skillsets and experience are to apply for the position. Depending on how the job listing is conducted, the clarity of day-to-day responsibilities can range broadly. The fact is no matter the description is very vague or very clear, the people will only “really” know what they are doing when doing them.

A lot of people I have come across will stop the job-hunting process when they see the required skillsets and experience of each listing. It is understandable if we think about the market mechanism, which we quickly have the X graph in our mind and think what we can provide will never meet what the market demands. I, on the contrary, think that the gap is an opportunity for growth. Additionally, I personally do not think learning a new skill or gaining the relevant experience is the hard part. The hard part is to know what I want to learn and that should be the intersection of PS, PfS, passion and the job requirements.

The safe approach is that our PS and PfS covers more than 60% of the job requirement and 20% matches our passion. If you are more of a risk-tasking person, you can go with 50-30. Bare in mind that we are analyzing based on our best knowledge but the reality is that the percentage for both are lower.

The rest 20% is what we save for PW and PfW. It is impossible to find a position to completely exclude them but it is possible to find the ones with the least. 20% is the hard goal and we should not allow it to be more than that. Otherwise, why are we even looking for a change?

In my career-switching journey, combining my personal strengths (logical, great collaborator), professional strengths (cloud technology, open-source technology and customer engagement) and passion (product team, program management), the direction seemed to be clear. But, even with all that, I still went through a few stops before I landed to an ideal spot. The details will be unraveled in the next part of this series.




Started my career as a consultant, moved to support engineer, service engineer and now a product manager. Trying to be a better PM systematically every day.