A Practical Guide To Changing Careers | Chapter Two

Find your dream job without it destroying your will to live?

It’s not uncommon to read career advice articles and see something along the lines of “Do what makes you happy”. That’s great advice, but also not very practical, right!?

What if you don’t know what makes you happy?

Even if you do, how do you begin to determine which of the things that make you happy, might even be a good career path for you?

You might love to travel, but that’s not an indication of the type of job you could apply for it’s just a broad interest. You could apply for a million different job types - from pilot to cruise line entertainer - under that interest alone.

In this chapter we’ll guide you through a process that lets you truly assess what your new career path should be. We’ll help you to identify your strengths, weaknesses, interests, and - if we’re lucky - your purpose. So that you don’t have to figure it out all by yourself … and we’ll hopefully put an end to those useless career advice articles too.

This is essentially a practical approach to defining the types of jobs that give you purpose and play to your strengths.By helping you to determine not just what makes you happy, but also your skills, and preferences. We can start to sketch the outline of what your dream job might look like.

In a sense you could say that we’re evolving the suggestion from “do what makes you happy” to “Make a career switch into a field you’re interested in with skills that you already have and with people that inspire you”.

But that’s not as catchy … right?

What is a dream job and how do I find mine?

There’s a lot of conflicting evidence online. Some sources say “the dream job doesn’t exist” and suggest that you “find ways to cope with a bad job”. Which is honestly a bit concerning.

But you also find statistics, like this one, that say: “22% of Americans have their dream job” - typically entrepreneurs made up the majority of people that reported this - but is this even true, or is it just American optimism / showmanship? Actually, for most Americans, it’s just an income threshold.

Surely there has to be more to a dream job than just making over $400,000 a year? What about happiness, purpose, being challenged, and harnessing your potential?

It’s important to know that a dream job is still a job. But finding a dream job has been shown to have a heap of benefits for people who go out of their way to attain them. That’s a big part of this process too, you do have to go out of your way, or take a different path, to find a career that gives you purpose.

A dream job is also unique to you, so understanding what your dream job looks like requires some reflection, some research, and some time. In a nutshell, finding your dream job is a journey, not a eureka moment. If you’re lucky, you already know what you want to do, you might have an idea, an interest that gives you purpose, or something you feel you would be great at, and feel inspired by.

For everyone else, and that’s most likely the majority of you, there’s a practical approach we can take to help you find the things you care about.

STEP ONE: What does your personal life tell us about your dream job?

You don’t have to do this on the spot, in fact should take your time with this. But write out at least one answer to the following questions about your interests, thoughts, and pass-times:

What do you dedicate your free time to?

- What videos do you watch on YouTube? (e.g. Casey Neistat)
- Why do you watch them? (e.g. Inspiration)

- What accounts do you follow on Instagram? (e.g. Call me 917)
- Why do you follow them? (e.g. Motivation)

- What books do you read? (e.g.Travel)
- Why do you read them? (e.g. Learn about places I haven’t been able to go to)

- What Podcasts do you listen to (e.g. Economics)
- Why do you listen to them? (e.g. To learn about how people and things work)

- What do you do in your free time (e.g. Photography/ceramics)
- Why do you do this? (e.g. To create aesthetically pleasing, unique things)

- How do you relax (e.g. Cycling / exercise)
- Why is this relaxing? (e.g. It gives me a sense of freedom)

What are some of the bigger events in your life?

- Have you or people you care about been affected by anything in your life? (e.g. poverty/identity crisis)

- What do people tell you you’re good at? (e.g. mentoring)

- What have you been awarded or celebrated for? (e.g. digital marketing)

- What made you feel good about yourself? (e.g. charity work)

- What are the things that keep you awake at night? (e.g. People suffering)

- Who are the people you admire? (e.g. Anthony Bourdain)

- Why do you admire them? (e.g. Sharing real, human experiences)

If that took you longer than you thought, welcome back!

Now that you have all that info, let’s define what the common themes are. This should give you a good idea about some of the broader subjects and interests that you already dedicate your time to, and therefore may also find purpose in. Based on the examples given alongside the questions above, we found that we already dedicated time to:

  • Learning about other people
  • Feeling inspired by other people
  • Doing things for other people
  • Creating things
  • Travel

These themes may already help to highlight some of the areas you should consider when thinking about your dream job.

For now, keep them in your back pocket as we’ll revisit them at the end of this chapter.

What’s next then?

What transferable skills do you have that lend themselves to your dream job?

Defining the skills you already have can help you to further understand what your dream job might look like.

One of the many things that prevents people from actually making a career move is that they feel they like they don’t have the skills to work in another field. What the majority of these people neglect is the fact that there are an abundance of skills that are required in any career. Not even just soft skills, although that’s a good place to start.

Whilst this fear may also just be a case of imposter syndrome, it’s worth taking the time to reassure yourself of your existing skills.

Below is a list of over one hundred skills - bare with us - that are needed in almost any job and you probably already have at least 50% of them. In fact, you can probably even give examples of way’s you’ve already excelled in them!

If you struggle to identify your strengths on your own, that’s okay too. Just think back to your last review, chat to your manager or colleagues, ask your friends and family and they’ll give you a great idea about where your strengths lay.

From the list below, highlight all of your skills:

Communication Skills

Able to listen



Nonverbal communication



Public speaking

Reading body language


Verbal communication

Visual communication

Writing reports and proposals

Writing skills


Conflict management

Conflict resolution


Decision making


Dispute resolution


Giving clear feedback




Managing difficult conversations

Managing remote teams

Managing virtual teams

Meeting management



Project management

Resolving issues

Successful coaching


Talent management

Critical Thinking Skills


Artistic sense


Critical observer

Critical thinking

Design sense

Desire to learn



Logical thinking

Problem solving



Thinking outside the box

Tolerant of change and uncertainty


Value education

Willingness to learn








High energy





Sense of humour

Work-life balance

Team work

Accept feedback


Customer service

Dealing with difficult situations

Dealing with office politics

Disability awareness

Diversity awareness

Emotional intelligence


Establishing interpersonal relationships

Dealing with difficult personalities

Intercultural competence

Interpersonal skills





Selling skills

Social skills

Team building

Team player

Work Ethic


Business ethics




Following direction

Highly organised


Making deadlines







Proper business etiquette









Staying on task

Strategic planning

Time management


Working well under pressure

What can we learn from this new-found set of abundant and transferable skills (apart from the fact that you’re already very experienced!)?

Well, let’s take a look at the skills you highlighted and determine the top categories that they fall under. Make a note of the categories, as you’ll need them later on.

Tip: If you find you have a reasonably even distribution of skills, pick the top categories that you identify with the most. For example, if you see yourself as a team player choose Teamwork as your top category.

What else can we learn from this?

Understanding your strengths AND weaknesses can help you to better communicate your skillset to others and plan your next steps.

Naturally, the next step is to look at the list of skills you didn’t pick and determine if they’re:

  1. Skills you should acquire (e.g. attention to detail)
  2. Skills you don’t need (e.g. high energy)

This process should allow you to start creating your path to your dream job - for example: by taking a leadership class you will create opportunities for you to grow, network, and develop your skills [and probably your confidence too].

It should also help you to recognise the opportunities that may not be right for you. Narrowing your options down and defining a clearer path to your dream career.

For example, not having “high energy”  means a job in Sales or Events probably isn’t a smart path to pursue.

What do you like about what you do now?

Whilst you may not be happy in your current career, there are likely to be aspects of it that you find more enjoyable than others. Maybe you’re great at writing reports, or get compliments for your ideas during creative meetings?

By identifying the things you like, dislike, or want to change. It can help put into perspective the things you might like to carry over into the next phase of your career (and your dream job).

Have a think about the questions below:

  • What do people come to you to do for them? (e.g. Reporting & Analysis)
  • What are you complimented on at work? (e.g. Problem Solving)
  • What interests you about your current career? (e.g. Helping People)
  • What do you enjoy doing in your current career? (e.g. Content Creation)
  • What do you like about the culture? (e.g. work with young people)
  • What do you like about the people? (e.g. it’s a small, friendly team)
  • What would make it even better? (e.g. transparency)

If you’re struggling here’s a tip:

If you can only see the negatives in your current career/job/workplace - you’re not alone - try to think about what you would like to change e.g. If you dislike that the size of a team limits your impact, then you might like to work as part of a smaller team.

There are just a couple more steps (we promise):

So, looking back at all of your answers across the first three steps. You should now be able to create a shortlist of your broad soft skills, personal, and professional interests.

Something that looks like this:

Personal Interests:
- Learning about people
- Doing things for people
- Creating things
- Travel

Soft Skills
- Communication
- Teamwork
- Critical Thinking

Professional Interests:
- Problem Solving
- Creating Content
- Helping People
- Small Team
- Young Professionals


You’re right, it’s not, yet.

There’s one last thing to think about: How do you like to work?

This might seem a little random, but it’s the difference between becoming a creator, a teacher, a manager, or a strategist

You don’t even just have to pick one option, but have an idea about your preferences as it’ll be useful in the next part of this process.

So which of the following approaches to you most identify with:

  • Creating
  • Teaching
  • Managing
  • Planning

You may already know the answer to this, but if you’re uncertain a personality test may also help at this stage (check out this test from 16 Personalities).


Now you have everything you need to start defining your dream job.

Below is a framework that should allow you to create some ideas about what your dream job might look like, or entail.

Remember, the aim isn’t to create one single, clearly defined path, but to work out some options and stepping stones. A starting point for the rest of your career.

Fill in the blanks in the following sentence:

“I want to use my interest in_______ (professional Interests) & my skills in _________ (soft skills) to undertake a  _________ (creative / teaching / planning / managing) role with a company dedicated to ______________ & _____________ (personal interests) and a team of ______________ (professional interests) that are focused on  ____________ (professional interests/personal interest)."

For example:

“I want to use Problem Solving & Teamwork skills to undertake a Planning & Management role with a company dedicated to Travel & Learning and a team of Young Professionals that are focused on Helping People.”

This should give you one fairly well defined job description (if not a number of them). A job description for your dream job! Or a job that is actually aligned with your interests, desires, and skills... for once.

Now when you come across the advice “why not do what makes you happy” you have an answer. You have a detailed breakdown of what that might actually be.

In the next chapter, we’ll dive deeper into how you can use this information to start building connections, motivation and actually get your dream job.

…. Obviously, go and Google the job description you created and see what results show up too though.


Much like changing careers, finding your dream job is HARD! Hopefully this chapter has helped you to answer this question: what am I interested in pursuing a career in?

Ultimately, knowing what you’re interested in, is the first step in finding your dream job. From here on, you can start your journey with direction and an end-goal.

That might be taking a class, reaching out to someone you know who already works in an industry you’re interested in, or even reaching out to a total stranger and asking to shadow them for a day.

Instead of feeling uncertain about your career, you can start to prepare yourself and plan the journey towards actually getting your dream job.

... whiiiiiiiiich, honestly, is maybe underselling how big of a task that is, but we’ll address that in the coming chapters of this guide.

If nothing else, you now have a better idea about the area in which your dream job might exist. Which is one hell of a lot more useful than being told to go and figure it out for yourself.