Finding Myself Again With “The Odyssey Plan”

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Hey Readers,

It’s approximately a month after my wedding (check out the behind the scenes in this video, thank you Chun Hwee!) and I’ve managed to find a job just in time before I finish my National Service and I am preparing for the arrival of little Evan some time in October.

The overlapping of these events have got me thinking and questioning myself on my identity.

I find myself frequently asking, “Who am I?” and “What do I truly want to do in my life?”

For the most part, however, I did not acknowledge these thoughts and feelings and often push them aside into the realm of “part and parcel of growing up”.

I then coincidentally came across a newsletter from Ali Abdaal (a productivity Youtuber that I’ve been following) where he shared his thoughts regarding how he felt the same way as well.

This inspired me to write this article, journaling my thoughts and do the exercise that he did called “The Odyssey Plan”.

What is the Odyssey Plan?

So what is the Odyssey Plan?

It’s an exercise taught by professors at the Stanford Life Design Lab where you answer 3 life questions in detail which apparently, should help you with answering questions like “What do I want to do in my life?” or whenever you are facing lots of changes.

If you are feeling the same, feel free to do these questions yourself too.

The 3 questions are:

  1. Write out, in detail, what your life would look like 5 years from now if you continued down your current path.
  2. Write out, in detail, what your life would look like 5 years from now if you took a completely different path.
  3. Write out, in detail, what your life would look like 5 years from now if money, social obligations, and what people would think, were irrelevant.

My Odyssey Plan

I have not thought about the answers while writing this article, so I will answer and think about them as I write. Here goes..

  1. I’m 25 years old and a newlywed living in Singapore, expecting to start my first full-time job in a month’s time and also preparing for the arrival of my first child. I am currently still serving my National Service and will be done in a month’s time.

    The job that I’ll be doing will be helping out a relatively “small” business in customer service, operations, perhaps marketing and business development. The business is expanding rather quickly and in the next few years, I see myself working closely with the founder thinking of different ways to reach out to more customers.

    Little Evan would’ve been 5 and I would be getting the keys to my first house, my humble Inline-skating side-hustle “HappySkates” should’ve grown larger and maybe having a small rental space with coaches to conduct classes and selling skating related products.

    I’ll be making small but consistent returns through my Forex journey, hopefully without spending too much time on it.

    This blog would’ve become much more personal, a place where I journal every once in awhile.

    My YouTube channel would’ve grown as I make more videos and currently looking to branch out into much more entertaining videos while providing value to my audience. Most importantly to have some fun throughout the process.

    Will be travelling more with my family and friends in the next 5 years and taking those trips to the places we’ve been longing to go.
  2. If I were to take a completely different path.. (this is hard to think about haha)

    The most logical yet different path I think I’ll be taking is to sign on with the Police Force while studying part time for a degree.

    My house will still be ready in 5 years and I see myself staying with the force for good.

    I will be spending much more time with my family and friends while focusing on my career. And after getting my degree, in that next 5 years, I may or may not leave the force and move on to a career related to my degree.

    Honestly, it is pretty typical (not in a bad way) and practical if I am not pursuing the path I am currently taking.
  3. This would be the best case scenario which I think unless you’re in a perfect world, it wouldn’t be happening but let’s do it for the sake of the exercise.

    I would probably bring my family and friends overseas and bought a holiday home, stayed there every few months and enjoy the simpler things in life such as fishing, surfing and hiking. (I personally feel this part of the exercise, though may seem redundant, helps you figure out the actual goals in the life you want.

What Now?

To be honest, I’m not sure if doing this exercise will really help me hahah but it at least got me thinking about the current steps I have to face in life. On the downside, it’s more of a goal-setting exercise than a “what should I do in my life” kind of exercise (in my opinion). Or rather, it’s an exercise to get your life back together and helps you to see what are the next steps you should focus on next.

At least it has helped me map out the good things that will be happening in the coming 5 years such as Evan turning 5, getting my house and the oversea trips I will be taking with my friends and family!


In conclusion, give it a try if you’d like it’s more of taking some time to reflect on your current life and the life you envision in the next 5 years.

Hope it helps and have a great week!

Quote of the week:

Do not spoil what you have by desiring what you have not; remember that what you now have was once among the things you only hoped for.