Career Change at 40

The Ultimate Guide to Career Change at 40 and Beyond 1
The Ultimate Guide to Career Change

at 40 and Beyond
Table of Contents
CAREER CHANGE AT 40 AND BEYOND 2
MAKING THE MOVE 4
Wishingwell Life Coaching © 2014

EXIT STRATEGY 5
KNOWING WHAT YOU’RE GETTING YOURSELF INTO 6
FINANCIAL SECURITY 7
USE YOUR EXPERIENCE - DON’T LOSE IT! 8
DOING SOMETHING MEANINGFUL TO YOU 10
FINDING YOUR PASSION 14

PASSION RULE NUMBER 1 19
MAKING YOUR MOVE 27
Career Change at 40 and Beyond

Career change at 40 and beyond can be scarier than career
change at an earlier stage in your career.
Why?
Because not only do you feel you have more responsibility, you
also probably feel you’re getting close to retirement, and are
“too old” for a change.

The stakes are too high to fail at this point in your life, and
therefore you feel you had really better get it right or you
might not have time to recover.
Yet you wouldn’t be here if you didn’t feel stuck.
You are probably having trouble knowing how to make the

move not because you lack the practical skills like how to
interview for a job, but you don’t want to leave the stability of
your current situation – even if you don’t like it – for something
so uncertain.
After all, with all of your responsibilities, how practical does it

really feel to jump head first into the unknown with no idea
which direction you want to go?
It seems impossible to figure out. Well, stop that thinking now!
Instead, it’s time to get excited.

You CAN figure out what you want to do next.
Not only that, but a career change now can be better than at
any other time in your life too.
Think about this – you have more freedom to do what you

want on your own terms than you have at any other point in
your career.
Anything you lack in energy will be made up for in skill,

wisdom and experience.
And you’re not that likely to make all the mistakes you’re
afraid you’re going to make, because your decision is going to
be a well thought out one.

It’s because you’re more mature, have responsibilities and
need to get this right that you’re going to take your career
change seriously.
You’re going to get the right resources, network with the right
people and get the right skills before you do anything big.
That’s why you’re here.
So let’s take a look at how this all works.
Making the Move

A career change at this point in your life into doing what you
love is a transition, not a flying leap.
For people with responsibilities like you and me, taking a flying
leap into something we think we’ll love just isn’t going to
happen.
Sure, you might fantasize about telling your boss that you’re
quitting today, but you can’t do that. (Well, you could, but you
wouldn’t like the consequences much! For some people who
really, really hate their jobs they do up and quit, but that’s a
special circumstance.)
But here’s the good news: You don’t have to take that flying
leap.

So forget what you’ve seen about a dramatic resignation, or

about leaving everything behind to live in a commune in India.
Doing what you love is a reality for people with responsibilities

just as much as it is for the 20-somethings without any.
It just looks a little different.
You’ll have to plan an exit strategy.

You’ll have to know what you’re getting yourself into.
You’ll have to have financial security the entire time.
It can still be done.
Every person’s situation is different, but the three elements

above (exit strategy, knowing what you’re getting into, and
financial security) will be huge factors in the transition.
Here are things to think about with regard to each one.
Let’s go over them in more detail:
Exit strategy
For some people, whatever comes next is something they can

ramp up while they are still working steadily.
For some, their current job may allow them to wind down
while their new job gains momentum.
And for others still they must work, save, plan and strategize
for a while as they work towards making the move more fully
at some future date.

Think about which of these is right for you.
In any case, you’re going to be working a main job for at least a

little while as you transition.
One very difficult thing to do is to remain focused and positive

at a job you don’t like while you make the move.
It can help to remember that this job is serving a function: it’s

allowing you at least the financial stability to make the move to
something better.
Hold onto that emotionally so that you can survive if your

current work situation has gotten very difficult.
Also, if you need a job for a while as your dream job or

business is in the works, you might consider doing something
else in the interim. For example, if you’re a qualified sales &
marketing rep, but you hate your company, go find work
somewhere else as you build your business. There’s no need to
suffer at a particular job any longer than you have to.
Knowing what you’re getting yourself into
Knowing what you’re getting yourself into means that you’ll

have to (as much as possible without being psychic!) know
what the next situation is likely to hold for you.
If you’re making a transition and there are things that you

could have or should have predicted that end up being
problems, you’re going to kick yourself.
So start by doing your research and thinking from the end.

Here’s an example I see quite often.
Many people come to me thinking they want to start a business

doing something, usually something like coaching or being a
yoga instructor or some other helping professional.
But after a little work together, what we discover is that while

they love the coaching/yoga/helping aspect, they don’t really
like the business aspect, nor do they believe they have the
skills to be successful.
They don’t enjoy marketing.
They don’t want to work long hours.
They don’t want to be “on the hook” the way small business
owners are financially.
Once they have figured out what they would have been getting
into, they realize the path they were heading down was
actually not right for them.
They reconsider, taking the helping skills that they do love to

use and reapplying them in a way that they will find enriching
and not draining.
You have to think about your situation and know what you’re
going to be getting yourself into.
Does it feel right for you?
Financial Security
This one is pretty self-explanatory.

You never want to feel like you don’t know where your next
paycheck is coming from, whether you’re transitioning to a
new job or starting a business.
Many people are tempted to quit jobs they hate so they can
focus full time on starting a business or looking for a new job.
I would never say you shouldn’t – there is something to be said

for putting it all on the line and not giving yourself an out –
when it has to get done it often finds a way.
But sometimes the financial stress of that situation is too much.

It can squash the creative energy you have, wreak havoc on
your sleep and health, and generally leave you in a worse place
than when you started.
You’ll have to think long and hard about this decision and how
you operate under pressure, and also what your current
financial situation is like and how bad the stress at work is for
you.
Sometimes making it happen is not just about wanting it bad

enough. There are things outside of our control that can go
wrong, and giving ourselves such a small margin for success
may be too stressful.
Use Your Experience - Don’t Lose It!

Many of you are probably thinking about moving to a career in

a completely new field, and at this point in your career you’ve
gained skills and expertise that you don’t want to leave behind.
Luckily for you, you don’t always have to kiss them goodbye.
There may be a powerful intersection of your skills and your

new field, or there may simply be a way in which you see your
new field from the perspective of someone who already has
earned her stripes.
What’s the perfect intersection of what you’re trained to do

and what you’d love to do?
Are there any similarities or skills that translate?
Even if the fields seem completely dissimilar, looking for

higher-level skills, like leading large groups, teaching, public
speaking, etc. can still translate and be valuable to an
employer.
No matter what, you’ll be bringing something novel to the

situation. That means you’ll have a chance to see your situation
in a new way, and be the one to bring fresh ideas and insights
to work that might be in dire need of innovation from someone
passionate about making improvements.
When it’s just you running your own business, you’ll find that
you’ve probably got what it takes, and any gaps that need
filling in terms of skills or experience can be quickly filled –
you’ll figure it out.

You’re much higher up on the food chain now - even if you
decide to make a move to a totally different industry, you have
years of experience in the workforce that will serve you well
no matter what you end up doing.
Doing Something Meaningful To You

If you’re looking to make a career change now, it might be
because you just don’t like your job or are tired of your
industry.
But it might be because you’re ready at this point in your life to

do something that means more to you than just a paycheck.
But if you’re like many people, having the desire to do

something more meaningful doesn’t mean you know what that
meaningful something is . . .
So how do you find it?
Ask yourself:
What do you want to do next?
This may sound like a simple question, but many of us overlook

the fact that our desires can drive things like our careers.

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We’re taught that careers and finances are serious business,

and that wants and feelings are to be kept out of it.
Even if you don’t believe this completely, there’s still probably

a part of you that was taught this. So you resist doing what you
want to do, because you believe it’s impractical. But it doesn’t
have to be by definition.
So start here, thinking about what you want, and then see if
you can figure out how that can get you paid.
I recognize that taking on that one statement – what you want

to do - might take you months or years to fully tackle.
But if there’s one thing that stops you from moving forward
with something you already find meaningful it’s fear.
Whether you’re at the very beginning of doing what you love –

just trying to find your passions and define your dream – or if
you’re on the other end, starting to make it happen, I’m sure of
one thing.
You’re afraid.
But you’re not as afraid of going for it as you think you are,
because there’s an even greater fear than going after your
dream.
And that’s never going after it.
Imagine it.

When it really is too late, you look back and you think about
what a shame it is that you wasted all your potential, gave
away all your time to things you didn’t care about, and never
saw what might have been . . .
The fears related to going for it are usually fears about failure
or success, or fears about what people will say.
But I challenge you to really think about it.
Which difficulty would you rather come up against?
The pain of regret - which you can’t do anything about - or the

struggles related to making your dream happen?
Thought so.
When you don’t know what you’re looking to do, people will
often encourage you to try to find your passions.
To me, passions are activities that get us fired up.
They are often the tools we use to accomplish our mission.
Our mission, sometimes called our ‘purpose’ or our ‘why’ is the

thing we want to accomplish in our lifetime or be engaged with
during our life.
Our mission is the thing that makes us feel “at home” or “on
purpose” and without it we feel a little lost in life, like we’re

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drifting and like there’s something we should be doing, but we

don’t quite know what it is.
I think people often say they want to find their passion when
what they’re truly seeking is their mission.
Passions without mission can be fun, but they sometimes lack a

deeper meaning.
This is why passions can seem all over the place – we have too
many, we sometimes get bored of them. They can lack the
substance of mission.
Mission can be an overarching life goal that can take on many

different forms during one’s lifetime. For example, one might
be a life-long teacher, and the form that takes on may look
different at different points in life.
Finding your mission looks a little different for everyone,

which is why a one size fits all prescription is so difficult to
create.
Just like in therapy, no two client experiences are the same. But
in therapy there is an overarching framework of how therapy
works , which consists of building an alliance with the client
and helping them re-write their negative story into a more
positive one.
The same is true for finding your mission, though the

framework is different. One of the elements for the framework

is that your whole life up until this point has been leading you
to it.
It can feel very difficult to see until you find it and then it’s like
it was staring you in the face the whole time.
An intense and personal approach to finding your passion and

your mission, like coaching, helps you because it is much easier
for someone to see this from an outside perspective than it is
to spot these patterns from inside your own life.
Finding Your Passion

You’ve heard over and over that passion is what you should be
looking for in a career.
And I have nothing at all against passion.
In fact, I think when we feel passionate about things we are

able to go that extra mile – we have the burning intrinsic desire
to do something because it’s “fun.”
But when it comes to building a great career, you have to think

about more than just fun.
You have to think about who you are as a person and what
means something to you – and that’s why this has all been so
hard to figure out.
The reason is that you’ve never been forced to define yourself.

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You don’t really know who you are.
You may disagree with me. After all this time on Earth you
probably think you know.
But I’m not talking about things like whether you enjoy art or
accounting. I’m not even talking about things like your Myers-
Briggs type or how many years of therapy you’ve been in.
I’m saying you still don’t know what resonates with your soul.
That’s why I get so many emails asking me “How do I come up

with good business ideas?”
And the truth is, I have no idea.
Because I don’t know what a good idea is for you.

Sure, I can help you discover it, but I can’t just pull it out of my
hat like a floppy-eared rabbit.
Something that might be dazzlingly fun for me could make you

shake in your boots.
And the thing that would be a dream come true for you would
make me want to pee my pants in fear. Or make me think about
gouging my eyes out because I’m so bored.
Before you can find THE thing, you have to know yourself. And
not just your personality. Your soul, too.

You’ve gotten here, to the point in your life when choosing
what you want to do with yourself is on the horizon, and now
you’re drawing a complete blank.
Or nearly complete.
Hey, I did it too. It’s human nature, I think.
Until you are faced with the question of what would you do if
you could do anything, you don’t really know what you’d do.
We’re never really taught to think about it.
But now that you’re there, or nearly there, to a place where you
have to decide what you’d do if you could do anything – maybe
because of impending retirement, maybe because you were
smart about your money and can afford to downshift to a less
demanding career, or maybe because you just hate your job so
much you’d rather take a flying leap into the unknown than
stay another year – you realize you have only a hazy idea of
what’s next for you.
So how do you actually answer the question, what would you do

if you could do anything?
Most people will tell you that you need to find your passion.
I think it’s important, but in truth, I don’t think it’s the right
place to start. Because passion is fickle. It will leave you as fast

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as your steamy young Italian lover, and then be back again the
next day, pleading with you and swearing its undying love. And
that just leaves you confused.
Instead, why not try and define yourself?
Passion is about what you love to do, but purpose – who you
are, what matters to you, or what you want to do with yourself
or more narrowly your career – is more about meaning.
When you think about who you are, what matters, or what
gives you meaning, what comes up for you?
What is your reason for being? Your WHY?
Of course, if the question were easy to answer we wouldn’t

struggle with it for so long. So what’s happening?
Sometimes we’re just afraid of being seen by others or of

seeing ourselves. There are lots of reasons why we find parts of
ourselves difficult to face.
So we keep those parts buried. Sometimes we’re listening too

closely to others and not closely enough to ourselves.
Perhaps we’re afraid of being called upon to be “brilliant,” and

so instead of stepping into our greatness we delude ourselves
into thinking we have no idea what we’re here to do.
But to find your purpose, you must to the opposite.

Be brave. See yourself. And when you think you’ve seen all you
believe there is to see, find someone smarter and more
insightful and braver than you who loves you enough to tell
you the things you don’t want to hear about yourself, but that
you have to hear in order to grow into the person you’re meant
to be.
Uncover those parts. Listen to yourself and SEE who you are.
ALL of it. Do that work. Because when it’s done what’s left is a
real understanding of who you are and what you have to offer.
Embrace your brilliance. Step into your greatness. Feel your

way toward what actually matters to you. Not what feels “fun”,
not even what feels “exciting.”
But toward what feels “kick-you-in-the-gut,” “this-is-it” “I-
have-to-do-this” experiences that tell you “If I don’t do this, I
don’t know what I’m doing with my life, and I’ll regret it
forever.”
When you get that feeling, you know you’re on the path toward
your purpose.
No matter how much I talk about purpose and meaning, its

prettier younger sister is always going to be passion. It just
gets more attention.
Maybe it’s just me, but I’d say there’s been a movement lately.
A movement all around how to live a passion based life. And

with any rebellion, there starts to become rules about how to
do it right – rules about how to rebel – which is sort of silly

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because isn’t the point of the rebellion to do your own thing in

the first place?
Whether or not you know it, you’ve become aware of a few

rules about the right (and wrong) way to do this passion based
life thing.
And doing it wrong gives you a lot of anxiety. I know that it

does because I get a lot of emails from you all with questions
and concerns about these things.
I want to break the rules of the passion based life so that you
know you don’t have to do it the way they say you do, but that
you can make up your own rules.
Let’s commence with the rule breaking now:
Passion Rule Number 1
You need to have just one passion – and if there’s more than
one you have to find a way to combine/condense them all into
one to have a successful career doing what you love.
Wrong.
Life’s just too full of interesting things not to be multi-

passionate, if you ask me. And the truth is, you don’t

necessarily have to choose just one thing to be the next thing
you do in your career.
It may be that you are able to easily do more than one thing
you’re passionate about in a single job (for example I get to
coach and write and be creative in the work I do), but if that
doesn’t work out for you, don’t worry.
Life will allow you to do everything you’re passionate about in

time.
Maybe you won’t do everything as a career. Some things you’ll

take up as hobbies, some as aspects of your career, and some
as major career focuses at different times in your life.
Also, if there’s one thing that’s constant, it’s change. So if you’re

looking forward to the day when you get to live out some
passionate dream you have, keep working towards and
planning for it. Your career can morph in the direction you
choose to take it.
Don’t fear that your passion has to be singular and static.

Passion is a living and breathing thing.
My passions won’t or can’t make me a lot of money.
Nope.

1
This simply isn’t true. Why should it be? Because many of us

are passionate about things that are “artistic” or are in some
way “softer” we automatically equate that with the idea that
we’re going to be doing what we do for love and not for money.
If this is what you want, there’s no problem with that. But if

you want to find a way to make your passion pay your bills,
there’s every reason to think that it’s possible.
The secret (yes, I’m spilling the beans here) is to structure your
business so that it actually makes you money, and to weigh
what you give up in doing so in terms of passion (if anything)
against what you gain in terms of income to find the sweet spot
for you.
With some creativity and deep thinking about what is really

right for you, you can structure a business that supports both
your passion and your lifestyle.
To follow my passions, I must live an unconventional, nomadic

or location-independent life.
Not unless you want to. Geez, this one really irks me. I get a
little frustrated with this one model of passion based living,
which is the “location independent lifestyle.”

Now, maybe you are ready to pick up and leave everything
behind if you just knew that one thing you really, really wanted
to do.
Maybe, if you sat straight up out of bed tomorrow and it hit you
like a thunderbolt, you’d pack your bags as quick as you could
and head for whatever exotic and sweaty location you were
called to, to carry out your mission.
But I’m guessing probably not.
I’m guessing that there’s more that ties you to wherever you
live than just not being 100% entirely sure of what comes next
for you.
There’s probably family of some sort. Friends. Obligations,

financial and otherwise.
And given all that, it would probably take you a while to make
this transition in the thoughtful and adult manner that you
make transitions and decisions in.
Do you worry that all this level-headedness makes you too

rational? Do you sometimes think you should pack your bags
as fast as possible and be spontaneous?
I think that only really works in the movies. It’s not all it’s
cracked up to be. The real path to fulfillment is not in being
rash, but in being honest – about your values, your needs and

3
about who you are and how you feel comfortable moving
through your life. Honor all of that.
Don’t think there’s only one model for embracing a passionate

life. You can take on a passionate life one step at a time from
right where you are.
I can’t start a business or get a job with my passions because

I’m not an “expert.”
Really?
First of all, chances are you’re probably more expert than you
give yourself credit for.
Second, even if you have some learning to do, there’s no reason

you can’t do it. You may decide that you don’t want to make the
investment it would take to become a doctor at this point in
your career – but that doesn’t mean a career in medicine is out
of your reach.
Whatever it is that you yearn to do, you can find a way to do it

and gain the skills and credentials you need to be paid to do it.

It’s too late.
This one really is a matter of choice. As mentioned in passion

based rule number 4, you might decide you don’t want to make
certain choices or sacrifices at this point in your life – and that
makes complete sense.
If it’s something you want so bad that you’re just distraught

that it feels “too late,” then you need to do everything in your
power to make it happen because no one wants to live with
that kind of regret.
But if not, think about it this way – it’s just life narrowing your
choices (thank you, Life!) because the number of choices really
is overwhelming anyway.
I don’t know how to start with a passion-based business or job.
Maybe you don’t know how to start now, but what about after
you do a little research?
What if you enlisted some help in the form of family, friends, or

coaching?
What if you put together a business plan or a job search

strategy?

5
Any big undertaking feels big until we tackle it systematically.

We often need a plan, some help and more than one tool in our
toolkit.
It’s too disruptive to my life/family.
What’s more disruptive: this move or your regret?
If making this move were a problem you HAD to solve, you’d

find a way to solve it, right? Well, think of it as a problem of
that magnitude. Because living with the regret, the never-
having-done, the might-haves and the missed experiences of
not solving it are just not acceptable.
Often, the disruptions that happen in lives and families because

of moves like this can be managed and minimized.
In fact, they can also often be seen as fun new adventures, too!
But whatever twists and turns life takes, staying stagnant
because of your family or some other part of your life doesn’t
have to be the final resolution.
I don’t know what I want to do, or what I think I want to do

isn’t really all that original or earth shattering.

You can figure out what you want to do.
Listen, I know you probably feel like you’ve beaten your head
against the wall about it. But I’ve worked with enough people
who were in exactly that spot who then got clarity to know
thatit can be done.
You need to look at what you like or love doing (or are
passionate about, but don’t get too caught up in that), and let
go of fears around it. You have to go down rabbit holes, ask
questions, make mistakes, back up and try again, but
eventually by feeling your way forward toward what is right
for you, you will find something that probably feels like it’s
been there all along in one form or the other.
Some people worry that they have a business idea but it’s not
completely new. That’s fine. In fact, that’s good because it
shouldn’t be completely new. You don’t want to reinvent the
business model, just improve how you do business so people
want to do business with YOU. Even a small improvement on
an idea can make all the difference – and sometimes it’s
people’s level of passion in the idea that is that special
something.
Maybe no one has told you until now, but you don’t have to
play by the rules. You get to make up your own rules. When it
comes to living a passion-based life, it really is about doing
what works for you.

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Making Your Move

I hope that I have shown you that while making a career move
might require planning and personal exploration, it’s not
impossible.
You probably found me through my post “Top 5 Tips for Career

Change at 40,” which says,
“Your major concern is probably that your relative age and

inexperience in your new career are a double-whammy.
The truth is, only your inexperience really matters, and luckily that’s
the one you can do something about.
Why?
People your same age with experience can find jobs. The higher -
level jobs, the ones that require a great deal of experience, are going
to pay more and be harder to land. And of course you can’t get years
of experience without years. So it follows that people filling these jobs
will be older.
The complete newbies are landing entry-level jobs. To compete

against them is difficult because they’re young and they don’t need
the paycheck you need.

So it makes sense that the jobs you’re going after will need you to
have some experience in your new field to be considered
competitive.”
Going into this move, one big question is “Is anyone going to
hire me?” The answer to that question will depend a great deal
on what you do right now.
Know that to be competitive, you may need to gain some

experience in your new field. You may need to get training.
There may be other things to consider.
That’s why it’s really great that you’re here. It shows that
you’re taking this process seriously and seeking information
about how this process might work.
You’re also open to the idea that you can learn things that will
improve your chances of success, which, believe it or not, is a
huge indication that you can be successful. You already believe
in your ability to make a difference in your own outcome.
So let’s embark on this journey together and see what we can

discover about you, about what’s next for you, and about what
you need to do to get there!
Beginning in December 2014, I will be starting Career Change

Coaching Circles.
They are intimate coaching calls, limited to 15 people, where I

will facilitate a group talking about career change, answering
questions, and coaching individuals in the group setting – we’ll
lay the ground rules before we start.

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It will be an incredible opportunity to learn and get coaching

around your career change for a very affordable price!
You can learn more and register here.
Every Monday I’ll be sending you an “Inspiration in Your

Inbox” email. It will include blog updates, insider news, new
programs, goodies, ideas, and freebies discounts and more.
Let me know if you have a question, want to schedule coaching,

if you just got a fabulous idea, want to share a resource, or if
something I sent you made you think.
I’m here to help you any way I can. So let me know what I can
do for you.
If you like this book, please consider sharing it! Just click the
bird!
With Love -- Jess

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The Ultimate Guide to Career Change at 40 and Beyond 1

The Ultimate Guide to Career Change

MAKING THE MOVE 4

Wishingwell Life Coaching © 2014

USE YOUR EXPERIENCE - DON’T LOSE IT! 8

DOING SOMETHING MEANINGFUL TO YOU 10

FINDING YOUR PASSION 14

MAKING YOUR MOVE 27