30 Tips for a Successful and (Fairly) Painless Career Change
Updated: Aug 2, 2021
Career change is a mine field. Explore the factors to consider before you set out in the pursuit of your dream career.
My career change was supposed to be easy. That was the plan. I knew what I wanted to do. I have had the clarity since I was 21: I want to be an entrepreneur! Then, there would be a simple plan and a quick implementation. Execution. Done.
Having performed a few major life changes previously, this was just yet another change. This time, without moving countries, packing up frantically, trans-Atlantic flights. With interesting awards. No downsides in my mind.
That’s what I thought.
In practice, it turned out to be far from easy.
There were tears, self-sabotage, guilt, shame, perceived judgment, fear of failure and procrastination. Together with leaps of growth and incredible learnings.
Spoiler alert: I’ve changed careers and feel very happy now.
I’m happy now to be sharing my tips and lessons from the journey. Although some of the tips I share might not be understood now, once you are moving, you’ll know when the same thing happens to you.
Here are my 30 lessons I wanted to share with you. It was initially just 10 lessons… But eventually I came up with 30.
I want to be honest with you so you know exactly what to expect if you hop on this journey, but also where I believe you can do better than I did - so learn from my mistakes!
1. Forget the “shoulds”. Do it for yourself.
Forget who or where you think you should be.
Or what you think you should be doing.
Or what you think your family thinks you should be doing.
The chances are you are using someone else’s criteria or your perception of their opinion.
A career change is something you need to do for yourself first. Why?
It’s not selfish. It really isn’t.
But you need to do it for yourself. When you are happy, the rest will also be happy.
First of all, it’s your career. If you’re changing the field of work, you might as well change into something you’ll love spending time on. You’ll not create as much value if you work on something you are not excited about.
Secondly, on the way to fulfilment and achievement, there’s no point in living other people’s ambition. You’re not showing your family the best example even though you might think so. You will be most successful if you do it in alignment with your values and beliefs, and where you know your potential can be optimized.
Thirdly, you do not want to find yourself late in life… regretting. I know I did not want to.
I think - and I’d love your opinion on that - that we all have 2 options:
one career that is a logical, easy to attain choice.
the second one is what I’d call the “secret career”. Something you’ve always wanted to do, even just for the sake of trying. Your family and closest friends don’t know about it. You do not talk about it.
Which one will you choose?
2. Get your people on board
You do not want to convince people to be on your side. It takes a lot of mental energy, and those around you might not be on board. They might be projecting their own fears on you, or just not want you to flourish.
However, if you can provide more information for them not to worry anymore, do that. You want as many ambassadors and cheerleaders as possible, and as much positive energy around you.
If you cannot make someone see your point of view, move on. They will see the result, but won’t witness the journey. And that’s ok.
3. Raise self-awareness
This part of the process is a very interesting one. And this is where you do your inner research.
I am yet to determine whether there can be a shortcut to this, or a sure-fire way to get this done within a certain timeframe.
What I do know is that it’s best accomplished through questions. And counterintuitively, the answers will not always pop up immediately. Why?
For some of the questions, your breakthroughs will come through self-observation. You’ll notice what you say, what you’re drawn to, what you spend Sundays and every morning on. “Follow the effort, not passion” advises Mark Cuban.
Other answers will be thrown suddenly by your subconscious. Over time.
Other insights will come from questions such as “what do I want?” - you’re studying your preferences, but also deciding on them. You cannot go for it all at once.
“What is it that I am fearing to lose through this career change?” - research your fears and beliefs.
Study your values.
Another interesting part of this research is to get feedback from your family, friends, mentors - regarding your strengths. This might surprise you what blindspots you might have.
Similarly, if you hire a career coach to figure this out, you’ll have someone by your side, unconditionally, who notices your body language, challenges you and holds you to a higher standard.
4. Study your beliefs
As you learn more about yourself, one extremely important topic is your beliefs. You do not want to have beliefs conflicting with your new vision of yourself and your world.
They will just make any implementation impossible.
Over time you’ll notice how you react to certain ideas. When someone says “you’ll earn 1 million”, do you think “it’s not for me”, or “yep! When?”, “I’m ready”?
Both reactions imply a different set of beliefs. Choose the beliefs to support your journey. And work on embodying them. Earlier said than done - I know.
Remove any roadblocks. Depending where you are in your journey, you might discover mindset blocks. Make sure to give yourself time to heal and bid farewell to those blocks.
Time to replace them with a new set of beliefs and to reinforce self-belief. This is of paramount importance. If this is not nailed in your mind, it will be hard to move ahead.
5. Build your criteria set
When choosing your options, you might instantly know what to go for.
However, if you want to be more methodical, build a set of criteria to guide your selection process.
A scorecard listing your criteria, so what the new job or new career needs to have.
All this to guide your decision making.
How much calmer will you feel if you know you’ve got the clarity of what you want? And that your selection process is not an ad hoc random one?
You know what drives you: is it money, work-life balance, possibility of hybrid work, emphasis on wellbeing, high position etc. This criteria may vary over time as your priorities shift.
A set of carefully chosen criteria makes the whole process an actual process. Nothing happens willy-nilly. You’ll feel so much more confident, peaceful and clear. This is also a sign you’re treating yourself seriously, while increasing the certainty of getting to the desired outcome and decreasing a possibility of future regrets.
6. Instant vs. delayed gratification
Vs. building for delayed results.
When crafting your options, you’ll see these 2 groups will be popping in your mind.
The “should” option - the logical next step in your career. You’ve been around for a while so this should be attained pretty quickly and easily. And you think your family is expecting it of you. Instant gratification is involved here.
Or the “could” option. Not as straightforward, but you know you’re made to do it. You might have not mentioned it to anyone ever (I call this your secret career desire) as you’d feel embarrassed for even daring to dream that big. But you know you’d be very happy and good doing it. This is also a more risky option, not as logical, not the logical next step… There will be delayed gratification.
A couple of things here… This needs to be solely your decision, without consideration of anyone or anything, at least for the start. You will need buy-in eventually.
But you need to be clear what you want to choose and what’s important now.
Just make sure not to postpone the choice of the delayed gratification option for too long in your life. What’s easy to obtain will not make you happy for long.
Even if it takes you 3 years to get where you want to be, and you might not like to be seen starting from scratch, uncertain and insecure… Well, attaining your goal and level of satisfaction will make it all worth it. Accept the challenge!
7. Build skills.
Skills are the basis of your futureproof career.
Once you’ve got the option selected and a plan built on how to get there, you need to review your skills.
What top skills will you need to build? It’s worth getting feedback from others, self-assess and break down skill groups into specific skills you’ll need to develop.
Look, you don’t need to go totally academic. You might not need a M.Sc. for all the skills. Google and YouTube are perfectly fine sources of information. Depending on what you want to learn, you might want to hack the learning and seek out experts to learn from. Just make sure you get started and not hide behind getting a qualification.
In this day and age, it should take you 3-6 months to build a skill. And anyway, you’ll be able to achieve it mainly through practice.
Just remember not to feel embarrassed about being incompetent at the beginning. Especially if your entire professional life you were good at everything.
If you cringe at the idea of being judged by others, buckle up. Because you will. But it should not matter to you.
It’s your fight and your skills. No one is doing it for you.
And even if you change careers again in the future… You’ve got a new skill in your portfolio!
For me right now? I’m building content creation skills. I broke it down into chunks and the first skill to tackle is copywriting. You see, I can go through life whining about how as a foreigner I’ll never be able to dominate the field. I choose to strive for excellence.
When I started doing videos on LinkedIn last year, I got mocked in person. And you know what? No one cares. Those who mock do it because they feel like they are missing something. It’s not about me. So bye, haters! Back to practising my craft.
8. Be extremely honest with yourself.
This point is crucial. And not only for career change. But just for everything you do in life.
If you want to improve yourself and an aspect of your professional or personal life, you need to be honest with yourself.
What do I really want? Am I being honest with myself? What’s my secret dream?
Where do I suck?
What do I do amazingly well?
Why am I in a point of pain in my career?
What do I need to improve about myself?
Is it possible that I perform self-sabotage?
Why do I not proceed with change?
Who do I need to become to get into the next level?
What’s my next step?
It’s not a matter of self-flagellation, but tweaking and moving on. Let’s be practical, while honest.
If you see you need to heal, take your time to do so. You’ve taken the first step.
9. Get radically responsible for your results.
When we are in enough pain, we tend to desperately look for solutions. And often to overestimate the power of others to induce change in our own lives.
The truth is though… Seek as much help as you wish. But treat all the mentors, coaches and therapists as your support council. And remember: you perform the change. No one else.
There will be no hand-holding or done-for-you. It’s all up to you to figure it all out and take action.
10. Embrace reinvention.
This is the cool bit of the process. You might be in pain now.
But imagine… You can choose and create anything you want. You can become anyone you want.
If you think big enough, this reinvention process can be a super exciting event in your life.
Whatever you dream of right now, there’s a path and plan to get there. And once you decide, reach clarity and kick off the process, you can get there quicker than you think! And I hope you surprise yourself.
11. Embrace your strengths.
Your strengths will help you build further competence and new skills, then confidence in turn.
Embrace them because it will make the whole career transition easier. And it make the new career creation so much more effective and efficient.
And whenever you have days of lower confidence, or maybe impostor syndrome is kicking in, you’ll always have the evidence in front of you: your strengths, to convince you and your brain that you can and will figure everything out.
12. Do not look to the sides. Comparison is the enemy.
I’ll repeat that: comparison is the enemy.
As much as we get accustomed to corporate ladders, performance reviews, looking at other people’s results to understand where we are on our paths… the truth is…
There is no one path.
And it is not a cliche.
You should always be working on laying your own path, and executing to the best of your ability.
The rest: positions, titles, salaries and cars… It is all irrelevant in comparison. And definitely nothing to focus on.
Work on your fundamentals. Look ahead. Never look back or to the sides.
13. Focus. Hyper-focus. Clarity.
Once you’ve worked on your options, chosen an option to go for with the imperfect information at hand, you’re clear on what to do next. You’ve planned. You know what you’ll do in the next 3-6 months. Or longer if necessary. But the main point: you’re clear.
Now: focus. Actually, now. Deploy hyperfocus.
It’s that much that this is important.
You’ll find it incredible how quickly you’ll be able to see results when you focus on 1 thing at a time. And work on it obsessively. Experiment, try and test.
Even if you feel there’s so much to do, always practice focus. Your mind will become calm and your output will be of higher quality.
You’ll thank yourself.
14. Learn new habits and unlearn the old ones.
Another success factor: habits.
This is where you also need to be very clear on what the new ones need to be to get the result you want.
And where you need to be very honest on what old habits to unlearn.
And both learning and unlearning is essential.
I’d advise you to review this on a weekly basis. And kick off with a week of observation.
Unlearn first to create space for the new. Build the new as it will still take time.
Try to build new habits one by one. You don't build all in 1 week.
Use old habit triggers to stack new habits. As in… You love to start your morning with coffee (trigger!). You go to the kitchen and what you see on your coffee table is a journal. You can easily start journaling (a new habit!) as you get your coffee.
Mindset-wise - see how you need to approach this with yourself: do you need to be strict to yourself? Or create comfort to be able to unlearn the old and learn the new?
15. Forget the (online) success stories.
Yep, forget the success stories. If they are not inspiring you, forget them.
But also… if they are… you also need to remember not all of them are actually true. The Internet is full of people who fake their success, or do not reveal the truth about the entirety of their journey.
A coach who tells you they created 6 figures in their business in the first 4 months. But they forget to mention they worked 3 years for free before that. All this to create authority with prospects.
All success stories need to be taken with a grain of salt. People tend to reveal the ups of the career change process, but not the downs. This will not sell. It will not show them in the best glorified light either.
This is also why I quite like to reveal my journey transparently. I just know the pain of feeling inadequate because I did not leave a job after 3 months… My memory is also good enough to remember the stories of online coaches and the gaps… None of my business what others say. But I also won’t allow that to affect my self-esteem.
16. You are doing it for you. You are not proving a point.
This is a tip which I believe has to be implemented more often, my more people… If you’ve built a foundation: self-belief, self-esteem and self-awareness, you do not need others to validate what you’re doing.
You do not need to prove a point to anyone who doubted you 20 years ago. Although I get the point and the fun of it.
You are doing it for you, your future and your people.
Adjust your view accordingly.
Make sure you also get rid of the clinging opinions of others.
This is your fight and only you care.
17. There is not just 1 path. Not 1 way to do things.
Although I am a fan of learning from others and picking useful tips on the way, I’ve learned this: there is not just one way to do things.
Not just one path.
Whatever your path is, it is what it is supposed to be.
It took me a moment to accept it. I am not an extremely patient person. But I learned my path and my timing is what I need to honour.
18. In case of a detour, do not worry. It is still serving you.
When we plan, we want the plan to be perfect, and then implement it perfectly.
The reality is there will always be a detour or some sort of redirection.
On my way from a corporate job to entrepreneurship… it was… a message from a headhunter with an offer for a Google job. Of course I went for it! And although there was a moment where I felt I was to blame for what in my mind were delays, I am now grateful for everything I learned through that experience.
Every experience serves you in ways you might not understand as and when it happens. Wait til you connect the dots!
There is a general obsession in society about the phenomenon of rejection. And I kind of don’t get it, in my naivety.
Ok, I know... no one likes to be rejected. And we have practiced it since we’re little… First loves, first tests at school, first exams.
I know I got evaluated, compared and rejected very many times.
If you take rejection as part of the process, you understand it is just natural it will happen sooner or later. Mathematically it just has to happen.
It can also mean redirection.
Or the timing is not right.
Or simply: try harder and come back again.
It is up to you to decode what rejection means for you in a certain context.
Accept disappointment and then do what you feel you need to do about it.
The same happens with failure. Everyone fears failure as if they were the only ones to have experienced it.
While, again, it is a natural part of life and any significant endeavor.
Hold on though: what does “failure” mean to you?
It is not experimenting, trying and not succeeding.
It is not quitting when you’ve changed your mind on what you want.
It is not taking a million years to get where you want.
To me, it is giving up on oneself. Not summoning the strength to try. Subduing to some beliefs that say you do not have permission so you should not even think about it. Only that.
Fear of failure is probably the most common one, felt by anyone and everyone who takes on a task of any size. If you feel it, it means you are doing something you care about. Keep going.
Fear of judgment of others might be an extremely powerful force, paralyzing our actions. Remember, we are social creatures. A lot of our actions are driven with the intent of avoidance of shame. This is a conditioning we’ve had for thousands of years.
When it comes to career change, you’ll need to grow a thick skin.
At the same time, be aware that people are self-centered, driven by their own problems and concerns. They really do not care that much about you.
Make sure you remove fear of judgment, coming from strangers or from relatives. It will affect you otherwise, and you will not be able to be yourself.
Once you’ve diagnosed this is what is restricting your actions, identify who these people are and why their opinion is important to you.
Have they judged you before?
Does their opinion normally mean a lot to you?
Or maybe it is irrational?
Get to the bottom of the issue. And choose to say goodbye to those thoughts.
If for some reason, and for a period of time, you need to stay away from them, do so. Whatever helps you get to the finish line.
You can also work with a coach or a therapist on all these fears. When they are mirrored to you, you’ll be able to understand them more thoroughly.
“I’m lazy!”, “I know what I need to do. Why can’t I get myself to execute the plan?”.
Actually, it’s never about being lazy. So please, don’t judge yourself. Do not feel eternally guilty.
When it comes to procrastination, there’s usually an underlying reason for it.
When you’re doing something new, it might be the fear, lack of self-belief or lack of clarity of the process.
It could be a lack of clarity. You’ve got options but still no decision on what to do. Maybe you’re a multipotentialite and you’re looking for that one perfect option. So you’re stuck.
It could be a lack of alignment. In other words, you are doing something you do not want to or what is not interesting to you.
Or simply, you overcommit and your agenda is overscheduled.
Once you spend a bit of time analyzing, you’ll figure it out.
You can tell, it is all a mind game?
This is where you can fully understand how contradictory human nature is.
On one hand, you know you’ve got the potential to pursue better and bigger things.
On the other, you do not feel like you deserve the big outcome you’ve envisaged.
I’ve suffered quite a bit from self-sabotage. It’s only when I found the source of lack of safety that kept me stuck and understood the reason, is when I could pretty much immediately kick self-sabotage to the curb.
And it was so empowering!
Talk to yourself nicely, give that self-sabotaging person a hug and tell them they are safe.
Now, let’s get back to work.
Before there’s confidence and competence, there has to be courage.
The reality of a career change is you’ll be scared and fearful.
The underlying fear is often… what will they say...
if they see me starting out?
If I seem ridiculous?
if I seem incompetent?
if no one buys?
If I need to start from scratch / from a lower position?
There will be more mental chatter than that.
From a practical standpoint, you can take 2 approaches… It’s like dipping into cold ocean water or into a swimming pool.
You can either ease into it… and suffer until you’re fully in the water.
Or take a plunge… be shocked and into it quicker.
Remember this. Although you might feel so many restrictions with your steps, the judgment, fear etc., your step is taken by many as a brave leap. So you shouldn’t agonize. Those who object are projecting their fears underlying their deep desires onto you. Showcase leadership. People are watching your courage and they do get inspired.
The only way to understand whether a decision to change careers is a good one is through empirics, i.e. through action and experimentation.
You just won’t know your success until you stop holding onto your last best thing in your career; to use the water metaphone - you need to stop holding on to the edge of the pool.
However, once you do that, remember that when you verify the parameters of you test, tweak and conclude you are not as interested in coaching a semi-pro football team as you thought you would, or that baking was fun as long as it was a hobby and not a full-time business, it’s ok to quit.
And I mean it.
I’m not saying it because I did it. I’m saying it because I saw people stuck in an awful situation just because they wanted to prove themselves and a point to others.
I prefer to see it as cutting losses.
In my testing phase, I started a coffee brand, an IG account, a blog and a couple of other things… The timing was not right and I was not ready but happy to test and learn. Happier to change my mind.
Once you know it’s the thing you want to pursue, you’ll know you need to exhaust all avenues until you get it right.
On the other hand, if you see yourself pausing and quitting too often, troubleshoot your process and intentions. Get aligned. Plan realistically. And it will all be ok.
26. There’s never a perfect plan.
As a project manager, and from a logical point of view, we all would love to have as much detail planned for this life-changing event. The thing is… There might be aspects of the change you might not be in control of. At the same time, if you don’t keep it too tight and closed-ended, you will leave room for opportunity and serendipity.
Especially as you’ll be learning a lot along the way. And not only about the rules of the new industry, but about yourself, above all else. So just keep that in mind.
For the start, try to plan as much to keep yourself on track. Define milestones and break down all goals into manageable chunks of work.
The change will feel so much more attainable straight away!
The point I’m trying to convey here is not to be sloppy in your planning, but to plan and then leave room for the learnings and tweaks.
One aspect I am still in two minds on is this: whether to have a plan B to Z, or not.
It might be easier for you to start, when you know there is a fallback plan. But you might also want to remove plan B, C…, Z, as soon as you know exactly what you want to do, and once you notice your own conviction and willingness to try out all the avenues until you get where you want to be.
Keeping an open mind and a perspective on where you are at, what you’re doing and what it all means in the grand scheme of things is so important.
If you think about it, you yourself will be your own biggest obstacle. You’ll set a goal and then strive to achieve it, and to get that recognition and sense of purpose.
You might also be more of an end-all be-all approach. With a more finite mindset.
The thing is… you can change careers as many times as you want. And you never actually start from scratch as long as you have skills and stack new ones upon them. As long as you keep on learning and growing. As long as you remove obstacles and trauma.
Not many things in life are irreversible.
Nothing lasts forever.
As long as you are good at what you do and a human being with a moral backbone, you’ll do fine anywhere your career path takes you.
So just don’t overthink, do not stress too much. Try it out. You don’t want to live in regret and with an idea you could have achieved something and become someone else. Keep the bigger picture in mind and stick to your vision.
28. Must-haves for the process.
A career change can look differently for many of us. There are a myriad of parameters to take into account. If I was to distill the fundamentals though - the make-or-break elements of the process, I’d bet on the following elements:
Self-exploration. This is where you explore your strengths, passions, preferences and criteria for your next career move. You raise self-awareness so you can also remove any stumbling blocks.
Research of the options of interest, both existing and the ones you have an opportunity to fill. Ensuring you know where the grass is actually greener.
Decision, based on criteria of choice, taken within a timeframe and using insights gathered over time. Risk mitigation plan.
First step taken in order to get into motion and gain momentum.
Experimentation. Testing. Trials and tweaks, followed by more action.
Solitude. There is a simple reason why this element is stated here, beside the necessary stages of a process. All the questions you’ll have regarding your choices need to be answered in the peace of your own mind. You’ll need support from your other half, and work in tandem if that’s what matters to you. But at the end of the day, you need to feel you are doing what’s right for you, even if it means taking a hit to your salary or a twist in your career path.
Simplicity. Every time you feel stuck, look for simplicity. What would you do if it was easy?
Since there are so many factors at play in the process, and usually so many requirements you might have for the process: for it to go fast, no downward movements, a perfect decision and plan diligently implemented. This, together with all the fears, perceptions and perceived opinions, can drive you crazy.
A lot will depend on the mindset you’ll adopt for the process. You want to be curious, keep an open mind, and experiment within calculated risks.
You might want to get help which is great and will help you grow and overcome limiting beliefs quicker. However… just a word of caution. The responsibility for the actions to be taken is on you. And you need to rely solely on yourself for the solution. I see too many people who crave a solution (and it might have happened to me). You’ll do whatever and pay any price to have your issue solved. The thing is… You need a toolkit and a new upgraded way of thinking. But you do not need any hand-holding. And you’ll know best what to work towards. This is where a coach will help with heightening your levels of self-awareness, which in turn allows you to make the right decisions, sustain self-belief and troubleshoot and problematic situations.
30. Choose the new you.
This one is a fun one.
I know everyone says change is hard. Because it is.
However, when it comes to career change, think of it as a fun project. You create your own challenge and your own future. Which can be delivered when you acquire a new set of skills and new ways of thinking.
Instead of the end-all be-all thinking, put on a scientist cap. Experiment. Prove a hypothesis.
Imagine a new you. Create that person. And then reach a new height. It really is fun.
Of course it’s difficult. You’d rather just progress steadily and that’s it. So why create those leaps?
Well, let me tell you one thing. Whatever your reason why is for the change, remember this. You know you can be more and do more. There is something within you, telling you your potential needs to be fulfilled. And that’s why you’re reading this article.
As any change, the career change is a process with various forces exerting force over who’s bravely taking on the endeavour.
You need to remember though… As much as you’ll listen to many people and take many factors at play into account, there’s really only one voice to listen to, and that’s YOU. And I mean it! Make your career happiness the driver of your career design. The rest of the reward you want to see in your life will follow. Be patient, persistent, and keep on going!