How To Design Your Dream Career

By Natalie Eng   •   7 min read

Recently while connecting with friends, I noticed that the topic of navigating careers has been common among different circles. Given the current situation where we are still pretty much stuck at home, I believe this extra time has given people more time to introspect and think about the next steps. Below are some thoughts on how I am going about crafting a dream career for myself and I hope this will be useful to you.

Note that this is just my opinion and I am still learning along the way as well so we are in this together 🙂

Why Is This Important

“How we spend our days is, of course, how we spend our lives’ – Annie Dillard

Research shows that in our lifetime, we will spend about 80,000 hours in our jobs. That’s approximately 30 years, for those of us who can’t or don’t want to retire early. Given that we spend the majority of our time at work, it’s incredibly important that we take some time to look at the bigger picture and strategise.

1. Change Your Mindset: Be Proactive And Take Ownership

In my opinion, this is the most essential step. More often than not, I see people waiting for some opportunity to fall into their laps, waiting for their managers/mentors to advise them on their career, waiting for a promotion. Instead of being reactive, why not just take control of your own career and create opportunities for yourself? This ensures that you (1) get to what your goal actually is and (2) in a much quicker fashion. Ultimately, you are 100% in charge of how your life pans out so you should be the one setting your agenda.

What I tell my friends, colleagues, juniors, direct reports:

  1. No one will care more about your career than yourself. Your manager has 1,000+ things on their minds: Their work, your work, their other reports’ work, their own advancement, their families, friends, etc. Your personal development will not be the top priority for your manager!
  2. Your manager/mentor is not telepathic. They will not know what you really want and why. Only you would know that. If you don’t even know what you want, how do you expect others to? This brings me to my 2nd point.

2. Reflect On Your Strengths and Interests

It’s much easier to thrive in a job that you are genuinely interested in that also plays to your strengths. This might come as common sense but I have come to find that common sense is not all that common after all. (Don’t worry – I made this mistake too. The important thing is learning from it!)

Additionally, it is also much easier to multiply your strengths than to make up for your weaknesses. It just gives you much more leverage for the same amount of effort.

If we are going to spend 60-80K hours in our jobs, what’re 1-2 hours every now and then to think about what energises and drains us so we can work towards landing a job that we are excited about!

3. Write Your Future Resume

This is about starting with the end in mind. Understanding where you ultimately want to be so you can work backward from there. This visualisation exercise is also something that many successful people do.

What’s your ideal career? And why?

I understand that this exercise can be scary and/or overwhelming but know that this is not set in stone – what you want can evolve together with you because you are continually evolving as a person as well. What you liked or wanted 5 years ago might not be the same at the present moment and that’s totally fine. People and priorities change. Heck, even the world is constantly changing. This exploratory exercise is still of value because it provides you with a direction.

You can create a future resume for yourself by thinking about job functions and industries that are of interest to you or the characteristics of it (e.g. it should offer me flexibility, autonomy, etc). This should also link to the 2nd point above on your Strengths and Interests. The difference here is that these are potential outcomes/outputs for those inputs. Do also think about the Why behind it – why do these roles/industries interest you? What about it makes for an ideal career for you?

One thing I did for myself was to check out LinkedIn and click on profiles of people who are in positions that I potentially want to be at and the career paths they took to get there. I liken it to creating a career Pinterest kind of board for myself.

4. Work Backwards To Understand Gaps

After getting a sense of where you want to go, you will gain a better understanding of how to get there. At the very least, you can approach people for help in a more specific/structured manner. For example, at least you can tell your manager/mentor that you have a rough goal of getting to X and ask if they have any advice to help you get there.

And/Or: Continuing from the LinkedIn example I gave above, based on all the profiles I have selected, I looked at each of their career journeys to see if there are any similarities.

For example:

  • Do they all have a particular experience/skill set that helps them to get to where they are?
  • Is that something I can gain from my current job or do I have to look outside for it?
  • Outside could mean seeking another job to helps you gain the skill set or taking up external training classes, seeking a mentor, reading more books of that area, etc.

5. Learn + Iterate

Last but not least, never be afraid to make mistakes or fail. See it instead as an adventure or journey. Realising what you don’t like is also as important as realising what you do like. Every opportunity can be used to discover this.

  • Think about whether your current work helps you to get to where you want to be
  • If it doesn’t, what have you learned from your current work about yourself i.e what you like or don’t like to do?
  • Knowing this, how would you map out your next step?If you have fears and doubts about trying out for a new role or if you should sink that amount of money for that course, ask yourself what’s the worst that could happen and see if you can mitigate that to make yourself feel better.

I understand that not everyone can try the all or nothing approach because we ultimately do have bills to pay. But also know that many times we do everything we can to cap our downside but yet not generate enough upside options for ourselves. See this career process as an iterative one that is continuously evolving and on-going instead of one “correct” destination that you have to get to.

Closing Thoughts

“Don’t ask what the world needs. Ask what makes you come alive, and go do it. Because what the world needs is people who have come alive.” – Howard Thurman

We have multiple great paths that we can choose from – see all of them as possibilities that you can explore instead of something that you have to get right as soon as possible. I hope this helps 🙂

On a side note, I am thinking about doing some coaching and/or videos around similar topics explored on this site. If this is of interest to you, do let me know here. Thank you!!


This article was first published on

Natalie Eng

TalentTribe Writer

Natalie is a Manager in the CEO's office of Style Theory, SEA’s biggest fashion subscription platform. In her role, she reports directly to the CEO and COO on key business strategies to grow the company. Her experiences include launching new business lines, streamlining current processes to optimise for efficiencies and building high performing teams. Prior to Style Theory, Natalie was a management consultant, serving private equity clients in different geographic regions like Brazil, Malaysia and China. Her past projects included advising private equity clients on acquisitions and asset sales as well as strategies to improve profitability. Outside of work, Natalie prides herself on having a strong growth mindset and inspiring people around her to be the best versions of themselves. She is a big advocate of living more intentionally and thus founded her own personal development community called NeverDrift in 2017. Natalie is also in the midst of being certified as a Professional Coach with the International Coaching Federation and serves with the Young Women's Leadership Connection in Singapore.


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