Career Transition 101: How to Make Big and Bold Changes


In the past month, I’ve been making my way across the globe to cities like Bangkok, Vancouver, and London to meet people on the road and start conversations around career transitions and unconventional routes to a successful life.

It has been amazing to hear everyone’s stories of what motivates them to seek an alternative solution to how they can live and work. 

Some people were corporates recovering from burnouts. 

Some were just fed up with climbing the 9-5 ladder without getting personal fulfillment from it all. 

Others were simply refusing to believe ‘this was all there is’, and were craving inspiration to get out there and do something different with their lives.

One of the biggest things I heard from people that were in transition to make big and bold changes for their careers were this:

People were craving communityThey felt alone in carving out the path to transition on their own.

People wanted to feel inspired by other people who are doing what they want to doThey simply wanted to meet a new community of people who believe in their dreams.

People needed accountability for their goalsThey were falling off the wagon too often when it comes to doing what is necessary to achieve their dreams.

People didn’t know what they were great atThis made them feel stuck on what to do if they were to quit their jobs.

If all of this sounds all too familiar, today’s blog post is for you.

[Don’t forget to register for my free masterclassReinvent Yourself:  How to Live Out Your Vision For a Meaningful Life and Careerwatch it here]


1. Make your choice and decide wholeheartedly that you want it

Decide to make a choice

When you decide that what you want in your life is your top priority, everything you do focuses to get you there.  One of the biggest game changers for people I’ve ever interviewed or studied for the Screw The Cubicle book or on Screw The Cubicle TV was the moment they made a distinct decision to make their dreams non negotiable

It wasn’t a “I’ll do it when the children grow up”, or “I’ll wait for when life isn’t as busy”.

The decision has to be made in your mindset that you deserve what you want, and you’ll do what it takes to bring your dreams into reality.  You may not need to know how yet, but you do need to know you want what you want.

Deciding to make a choice is the first step to get your heart and mind ready to receive what is necessary to make changes in your life.

Define what success and a good life means to you

One of the biggest reasons why most of us are dissatisfied with our careers and lifestyle is because we got busy creating a version of success that weren’t ours.

It was defined to us by society, our teachers, our parents, and what we believe we HAVE to do.  Not what we WANT to do.

Once you feel a misalignment with your current life path, whether it comes to you in a form of a burnout, health scare, unhappiness, or all of the above, THIS is your opportunity to redefine what success means to you instead.

You have gone down the route of what doesn’t work.  Let’s find out what DOES work.

I remembered when I was struggling to quit a high paying job in exchange for an unknown road of entrepreneurship.  It was difficult for me to justify giving up a six figure job for a ‘chance’ of freedom.

I had to really understand what a successful life and career meant to me.

For the longest time, I thought it was about the money (you too, right?).  But I received that money.  I bought a house, car, and nice things with that money.

It sure as hell didn’t get me closer to feeling successful.

So if money doesn’t buy happiness and the feeling of success, then what?  What would I REALLY want to experience with all these buckets of money I felt I had to have?

When I started writing it down, it surprised me that things that made me feel fulfilled and meaningful in my life were sometimes the simplest things.

Success and a good life to me was what I was experiencing every day.

And those experiences didn’t cost as much as I thought.

That helped me make that trade from a six figure job to an unknown path of independent working.  I did not have to make six figures to have a good life..today.  Not when I’m 65, but right now – read my blog on how I live in a tropical paradise for less than $1,000/month.


2. Act before you think you’re ready

Small incremental moves leads to results

When I facilitated meetups in the last month in several communities, so many people came to me to tell me that they have had ideas brewing in the back burner for so long, but they’ve been waiting for the perfect time or the perfect solution before they made a move.

I’m here to tell you to stop this right now (with love).

Every small move you make to create active changes in your life matters, big time.  Every conversation you have, every thought you change, every skill you learn, all leads to small incremental steps towards the results you are craving.

But you gotta move.

Think about one thing you can do each week (or even each day) that will chip a little bit more towards your goals.

It can be simple things.  Ask someone for help.  Read a book someone recommended.  Join an online community to ask questions.  Help someone with what you know.

Every move you make (and every breath you take – The Police fans, anyone?) creates the difference between getting what you want and hoping for what you want.

Create value-driven actions and decisions every single day

Don’t just be a sheep in the online world duplicating what everyone tells you to do.  Listen to the advice, and make it your own.  But always check in with yourself whether each strategy, tip, or advice you get is also one that is in tune with your values.

Just because it works for someone else doesn’t mean it’ll work for you.

Whatever action you decide on to create a new career or reinvent your lifestyle, make sure it links to how YOU want to live your life.  If it feels sleazy, don’t do it.  If it shakes up your ethics, walk away.

Seek mentorship, but find your route of doing it your way.  That’s the point of a freedom-based career and lifestyle anyway.

Start where you are

Everything you know now, puts you in the perfect place to start today.  You do know enough.  You are equipped enough. 

You are enough.

Give yourself the permission to know that everything you’ve experienced so far in life has led you to be ready for where you want to go.

Consistently put yourself out there and do the work.  That means if you are curious about something, make the moves to see where it goes. 

Start that research.  Sleuth a competitor.  Ask someone about the industry or career type you are interested in.  Help someone with a problem you think you may be interested in solving as a job.

As you expand into different horizons, your knowledge and expertise expands with you.


3. Side hustle while still in your full time job

Start small and look for ways to repurpose what you know

One of the questions I got asked the most is “How do I know what I’m good at to create a business from?”

Well, sometimes you don’t know until you do it.

My advice is always to start small, and test different paths, without overcomplicating the process.

If you’re in a stage where you may not know what you’re great at, or are good at multiple things and need some focus on your career niche, start with the best skill or strength that have gotten you paid or recognized in the past.

Repurposing what you know into a new career is a low hanging fruit opportunity that may be best for you to start at.

Perhaps you’ve been a good financial advisor, but you do not want to work for a bank anymore.  So instead, could you re-use that knowledge into a new direction?  Perhaps it’s mentoring millennials on how to plan for their future with a better money mindset.  Or helping women who are starting a business to plan and budget for their dream business. 

There are multiple ways to repurpose your skills to create a new direction for your talents.  You can breathe new life with old knowledge simply by changing who you help, how you help, and why you help.

Same knowledge, new focus.

Experiment, test, and adapt your ideas

In the beginning stage of dreaming up a business idea or career direction, it’s essential that you create an environment where you can experiment with your ideas and test where you can take them.

Get out there in the playing field and ask questions.

There’s no need for a website or anything shiny to start this.  You simply must be curious about figuring out how to solve problems for people.

Use social media to your advantage by using platforms like Facebook groups where you think your potential clients may be hanging out and learn to ask questions.

People love giving their opinions.  Especially if you are committed to helping them.

Use this stage to dig deeper into what people struggle with by asking specific questions on the problem you think you want to help solve.  Ask them how they currently deal with the problem and what they wish they could learn.  Get on the phone with people.  I like using a 30 for 30 exchange format – 30 minutes of surveying them, and they get 30 minutes of free advice/coaching as an exchange.

The point is to use all these real valuable insights to help you create a solution you can sell in your business.


4. Community and people matter

Surround yourself with people who are doing what you dream to do

As humans, we are like sponges.  We become who we hang out with most often.

If you are surrounded by people who aren’t living a type of life that you want to have or believe in (don’t worry, it’s not a personal thing), you need to start talking to different people.

When we are able to meet people that are like-minded and share common values that we have in our lives, we can become more courageous in reaching for our dreams.  They believe in us and they get our ‘why’.

Now imagine being around people who are DOING what you dream to do.  Seeing real people do the things we dream to do can be a very powerful thing to change our belief systems of what we dream to do.

You can hear their stories and get their advice of how they got to their success.  They can help you bypass the unknown.

Change the community around you, and change the reality of what you can achieve.


5. Change what you know and see ‘problems’ from a new view

Your attitude determines whether you see opportunities or setbacks

Mindset and attitude is the most important thing you’ll need to transition from being an employee to an entrepreneur.

Being an entrepreneur means that you create your own solutions, not wait for someone to do it for you.  If you hit a wall, you find a way to go over or around it.

However, to see these solutions, you need to have a positive perspective.

You have to see your circumstances with an attitude that wants to see opportunities rather than setbacks.  Your intentions must be focused on using so called ‘failures’ and ‘setbacks’ as stepping stones or clues to alternative possibilities.

Get curious as to what new door you can take.  Explore what didn’t work to lead you to what can work.  Breathe in, breathe out, dust yourself off, and keep going.

Perseverance is the name of the game

What makes a successful entrepreneur?  Perseverance.

Perseverance = persistence in doing something despite difficulty or delay in achieving success.

My friends, you will get somewhere if you keep going.  But if you stop, you fail by default.

Steve Jobs said, “I’m convinced that about half of what separates the successful entrepreneurs from the non-successful ones is pure perseverance”.

Most people give up at the first sight of an obstacle, when really, that obstacle had key insights and answers to what their next step should be.

In order to keep persevering, you need to redefine what you believe is ‘failure’.


6. Disrupt your routine

Don’t let monotony suck you into a ‘not bad enough’ life

We are creatures of habit, but we must also choose to change things if those habits aren’t leading us to a life experience we want to have.

Most of us that live in the western first world may suffer from the ‘not bad enough’ syndrome that keeps us even more stuck in circumstances that aren’t making us happy.

I know it was true in my case where it took a mental breakdown and burnout to finally wake me up to the fact that my life was extremely dissatisfying and unhappy.

Don’t wait until something major happens to create change.

If you have an inclination that something isn’t right or where you are isn’t where you want to be, trust that feeling.


Reinvent your career and create a major shift in how you live and work

Making big and bold moves in your career transition can be daunting, especially if you’re doing it alone.

Join my free masterclass to get the help you need in your transition journey.

Register now to watch how to you can reinvent yourself to live out your vision for a meaningful life and career.