How to decide on the right career opportunity for you.

A guide on how to prioritise options, reverse engineer your goals, use the right information and trust your intuition.

Hello Hello

Writing from Cyprus again after two weeks back in London. I had the opportunity to fly back before London lockdown kicked in, so am feeling extremely grateful to have a base out here and being able to sort the fit-to-fly covid test in the nick of time.

Wherever you are right now, I hope you’re staying safe, and looking after yourself in these testing times.

Since the last newsletter, I’ve been coaching the current Le Wagon London cohort, from Mon-Fri for the last two weeks as the students begin to define what they will do after they finish the Bootcamp. 

With the help of my amazing associate coach Melanie, 90 people had coaching to align on their next career steps and to troubleshoot any presenting challenges.

In todays newsletter I’ve captured some of the questions, methods, and practices we used to help people distill the best next steps for them.

The advice and framework to follow applies no matter which line of work you are exploring.


PS, if you enjoy this newsletter you’ll get some value from the podcast I was featured on last week with Marc Champagne from Behind The Human.

You can listen here. I delved into some of the questions to ask yourself when navigating times of reflection in your life & career. (Global pandemic, anyone!?)


So here are some of the principles to use when deciding on the right career opportunity for you:

1-  Decide what you are optimising for right now

The answer to this question determines what needs to happen next. 

Certain factors will be more important to you in your life right now than others.

You should prioritise one or two factors that are most important based on your current needs and circumstances:

  • Stability - Do you want your next option to provide reliable income, security, and a clearly defined road ahead?

  • Learning - Are you mostly optimising for learning in this next career phase and maximising your professional development?

  • Creativity - Are you craving the ability to ideate, put your stamp on something?

  • Freedom - Do you need to be able to move around freely, to turn work on and off at your choosing, to travel?

  • Wealth - Are you saving for important life events or want to maximise your earning potential?

Some choices will provide you a few of these at once but rarely all. This is not an exhaustive list but the point is that trade offs have to be made somewhere, and so will determine which factors you prioritise. Freedom and stability likely will come at odds to one another, for example.

2 - Work backward from your end goal

Perhaps you’re open to what this stage offers you out of the list above, but you do have a specific end goal in mind for a later life phase.

Think of it this way:

If you’re unclear about what to do right now, you can use the information you do have.

You know where you’ve been and you might know where you want to end up. So the gap in the middle is what you don’t yet know about, but you can learn by figuring out what will bridge the gap between what you’ve done with where you where you want to go. This forces you to make some choices and gives clues about what is most important to do. By working backward from your end goal you can figure out what you should be doing in the lead time that will maximise the chances of that happening.  


3 - Look internally before you look externally

When making choices about careers its natural to seek inspiration from the external world: the internet, our peers, mentors, family and colleagues etc.

But before you ask them what you should do, look internally at your own inner world.

i) Take stock of what you’ve already done. Analysing your career to date helps you look objectively at your achievements and experiences. Draw out the commonalities and threads between the things you have enjoyed and excelled at. Do the same for the things you disliked.  Use this information to help you filter the right from the wrong.

ii) Know your personal values. By outlining these you are better placed to make decisions that are in alignment and from which you can judge your success against.  This piece can help with your values if you’ve not done yours yet.

iii) Decide for yourself, what is that you want to be doing with your time each working day? The answer to this question determines which next step will create the most joy for you. As a Coach for example I could easily get away without doing much writing, but I love writing and have always longed to find a way to weave it into my work. I’ve designed this newsletter intentionally around this piece of self-knowledge, to maximise my fulfilment.


4 - Get all the information you need

If you are faced between various choices, ensure you are making choices with the right information available. 

It’s important you’ve not created any binaries “it must be x or y”. We live in a world of abundance (even if it doesn’t always seem that way) so by expanding your horizons of what might be possible for you, other avenues for exploration reveal themselves.

You also want to check how you are deciding on various options. Are your beliefs and assumptions accurate? Do you need a different perspective? This is where coaching can help provide an objective lens (unlike family & friends who may be biased toward a certain outcome). 

This list of questions from Annie Duke’s book, Thinking In Bets, can help guide you.

  • Why might my belief not be true? 

  • What other evidence might be out there bearing on my belief? 

  • Are there similar areas I can look toward to gauge whether similar beliefs to mine are true? 

  • What sources of information could I have missed or minimized on the way to reaching my belief? 

  • What are the reasons someone else could have a different belief, what’s their support, and why might they be right instead of me? 

  • What other perspectives are there as to why things turned out the way they did?

5 - Tap into your resources

Use the people, resources, and tools available to you. List out all the options you have and brainstorm what else you may have initially overlooked.

Other people can shortcut the time it takes to learn something. Tap into what other people know by asking them, even if they are strangers on the internet. Seek their input and hard-earned experiences by reaching out, explaining your situation, and why you feel they may be able to share some insights. You’ll be surprised how many people are open to this, whilst people on the internet may feel like strangers who you imagine don’t want to be disturbed - with the right approach - can be turned into trusted allies and sources of information.  My post on online networking offers some tactical approaches here.

So who can introduce you to someone, lend a hand to look over your CV or portfolio, or give you a warts and all version of where they work?

6 - Trust your gut

With all these pointers it can sound as though there is a logical process to follow to make decisions. I try to provide frameworks for career choices you can use after seeing so many people pick ill-fitting career choices and cannot pinpoint what went wrong. 

Yet whilst I aim to break down the components into actionable strategies I also want to emphasise that above all else, sometimes you have to simply listen to the small still voice within. 

What is that voice telling you?

My intuition told me to quit a job in December last year, despite having no back up plan and a new mortgage to pay. That decision prevented me from being part of a company that layoff 70% of its team. That decision gave me enough time to get set up as self-employed and gain momentum before the pandemic hit. Had I chosen to ignore that inner voice (the warning sign) its unlikely be writing this newsletter today with the experiences I’ve had in my career and business this year behind me.

Sometimes you do know what you want really, you just have to listen to yourself.


I hope you found this framework helpful and as always hit reply if you want to discuss anything with me in the emails, and clicking the tiny ❤️ button lets me know you’ve gained some value.

(As a reminder there will be no newsletter next week as I’m on a bi-weekly publishing schedule for the time being!).