August 28, 2025 • 8 mins
Have you ever thought you landed your dream job—only to realize it was just comfortable? In this episode, I open up about what it’s really like to hit a career crossroads at 40.
I share my personal journey of thinking I had my “forever” job, only to be forced into an unexpected pivot. That moment became the shock I needed to leave my old firm, build my own practice, and run it successfully for nearly a decade.
This episode is a reminder that reaching a turning point in your late 30s or 40s is not the end of your career. It may be the chance to rebuild, refocus, and redefine your path.
If you’ve ever asked yourself “What’s next for me?”—this conversation is for you.
Become a supporter of this podcast: https://www.spreaker.com/podcast/in-the-know-with-tony-reeves--5596987/support.
I share my personal journey of thinking I had my “forever” job, only to be forced into an unexpected pivot. That moment became the shock I needed to leave my old firm, build my own practice, and run it successfully for nearly a decade.
This episode is a reminder that reaching a turning point in your late 30s or 40s is not the end of your career. It may be the chance to rebuild, refocus, and redefine your path.
If you’ve ever asked yourself “What’s next for me?”—this conversation is for you.
Become a supporter of this podcast: https://www.spreaker.com/podcast/in-the-know-with-tony-reeves--5596987/support.
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
And in the good evening everyone in the red Tony
reads you read, Tony read bier following the news that's
right shape or no sortage of things to talk about?
Speaker 2 (00:15):
What did read? What will? This is a reality. We
simply have to step by me, read.
Speaker 1 (00:23):
Me, read, Let's go ahead and kids started.
Speaker 2 (00:31):
At thirty eight, I thought I found my forever job
until I was told I need to do more, and
that just shook me to the core. So what do
you do when the career you thought you were going
to have forever turns out to be very uncertain? Let's
get at it. One are the dangers that happens that
over time, as you move through your profession. If you're lucky,
you may find yourself in what I call a comfortable job,
(00:53):
one that's stable, one that gives you the support you need,
one that satisfies all of your financial requirements as well
as your cultural vironments. And all of a sudden, you
may find yourself believing you have now acquired your dream job.
That means a job that's going to allow you to
do all the things that you want to do during
your personal life and your professional life during the course
of your employment there and as such, because you've just
(01:14):
decided decided this is your dream job. You are not
taking any actions to do anything more than to do
everything possible to stay at that job as long as possible.
And for me, I found myself in that same spot
when I was around thirty eight years old. I thought
I was in a position where I believed that I
was at a dream job, that I was at a
job that I was going to be at for the
remainder of my career. I had been there about five
(01:35):
years and they literally supported me in all of my endeavors,
not only inside projects but outside projects as well as
providing a support network for me with my personal activities
as well as professional And there's nothing wrong with having
a dream job, and there's nothing wrong if you believe
you have a dream job. But there is a problem
if there's a turn you didn't expect. In my case,
(01:56):
it was being told after working for a firm, that
I was needed to do more in order to demonstrate
that I could go up in a higher position within
the company. Now, just merely being told to do more
and of itself, is not problematic. The problem within this
particular instance is that up to that point I was
instructed and provided information indicating that I had been doing
everything I needed to do to evolve accordingly. But now,
(02:18):
for the very first time, I was being told that
I hadn't done enough, even though I was under the
impression based on information I received that I hadn't done enough.
And now I'm being told that I needed to do
more in order to be able to get to the
next level internally within the organization. This concept of doing
more without any clear cut direction in terms of specified goals,
specified target objectives, things of that nature, created a measure
(02:42):
of uncertainty that I had never experienced during the time
that I had been there. So now I found myself
in this unique position of starting to realize that maybe
the company that I was working for, the firm I
was working for the long term commitment may not have
necessarily included me in that calculation. So now I found
myself with a really difficult challenge because I was at
(03:02):
a company who had been loyal and supportive of me
for this entire time period, but I was now facing
the fact that I was comparing the loyalty to the
realization that I needed to now not look at this
place as a place that I was going to be
at for the long haul and wondering what does that
mean for me if I choose to endeavor to try
to stay longer, or if I needed to look in
a different direction. This is where you get to what
(03:23):
I call the crossroad decision, because you're not just balancing
your own decision, you're looking at everything in its totality.
For me, I had to decide did I want to
stay and hope that everything that I was doing going
for would get me to the desired direction, or did
I want to start seeking other opportunity outside with the
uncertainty of whether I would find a place that was
(03:44):
similarly situated to where I was at, or if I
needed to entertain the lot of going on my own.
And it wasn't just merely focusing on what my next
professional objectives were. I still had a lot of other
things to take consideration as well. I had a card note,
I had a mortgage, I was married. I had all
these responsibilities that I had that were directly tied to
the job that I currently had, and so now I
(04:05):
was looking at possibly disrupting that all together, and I
didn't know what that would mean going forward. But the
hardest part is when you have all these responsibilities, it
sometimes makes you forget about how you manage to get
to this point to begin with. In other words, for
someone like myself, I had made career pivots before. This
wasn't a newer phenomenon, so I had a proven track
record of pivoting and being able to do so. But
(04:27):
the difficult thing I faced was that this part of
my life, as I was heading to thirty eight thirty
nine years of age, I didn't think I necessarily had
to make that pivot anymore. I was yearning to be
in a position where if I had to evolve, it
would happen organically internally at one place, and not me
having to physically go do something else. For me, the
decision was to start my own firm, and it wasn't
(04:49):
an easy one. It's what you have to call, ultimately
the leap of faith because I had no idea what
to expect. I had never run my own business before.
I was starting a new business with nobody at all.
Literally was taking advantage of opportunities that some of my
colleagues had provided to me, as well as referrals as
well as using their office space, and I still had
to be mindful of all my financial responsibilities, which included
(05:11):
a mortgage, which included the car, node which included bills.
All of these things, and even though I had my
wife who was also working that provided a measure of
comfort as well. The reality is is that these things
didn't go away just because I no longer was working
for my prior firm and I had now created my own.
But fortunately, two years afterwards, I was still going strong,
and I would remain strong for the next seven to
(05:33):
eight years. And it was this resiliency that helped me
feel more comfortable with the reality that I had made
the right decision. So by the time I had turned forty,
it did not feel like I had taken a step back.
I had just moved in a different direction to build
upon my skill sets and build upon my ability to
do things I had to anticipated. So what did I
(05:53):
learn when I learned that skills are transferable, So never
underestimate yourself. A lot of times what happens is that
you I think that the only person that truly values
your skills is the company that you work for, because
they're u lizing your skills to do something for them.
So there's a natural inclination to think that only your
job will pay for or value the skills that you
have when you don't realize that there are plenty of
(06:14):
people out there and opportunities out there that will take
advantage of those skills if you put yourself on the
right platform to be able to allow them to take
advantage of them. Two, don't fall into the cruise control
or your dream job. That's one of the hardest thing
to do because a lot of us crave stability, and
there's nothing wrong with that. A lot of us crave comfort,
nothing wrong with that as well. But the danger that
sometimes happens is that when you put your hands and
(06:34):
your livelihood and your future into the hands of one
specific group of individuals with the thought that they are
going to create this environment that's going to stay with
you for a particular period of time, there's always the
potential that something could happen to that job that could
shake or undermine exactly what it is that you value
in terms of stability. Third, and finally, crossroads are opportunity
(06:56):
for growth. A lot of times what happens is that
because we stay so laser folks on doing what we
do on a day to day basis, taking advantage of
the fact that we have an employer that's paying for
us to do certain things that we don't realize that.
One of the great things that may be kind of
tough things that comes from being at a crossroads that
forces you to look at things differently is that it
forces you to also grow. When you are now in
(07:17):
a position where you start to realize that your current
circumstances may change, whether it be because you're going to
have to change it or somebody's gonna have to change
it for you, you may find that this might be the
best time to start exploring skill set that you didn't
even realize that you had, or more importantly, skills that
you didn't fully maximize until put in a position where
you had to do so. I realized I was built
for this, and so are you. A lot of times
(07:39):
it takes being put in these positions to show you
and remind you that you are the person that got
to where you are today because of how resilient you are.
And never let the fact that you have been in
a position where you've been kind of on cruise control
have you doubting all of the energy that you put
into it gets you to that point. If you're at
a crossroads. Just remember three things. Trust your decision, trust
(08:03):
your resilience, and recognize you can. You will never go
wrong betting on yourself.
Speaker 1 (08:09):
M m hmmmmmm hmm
And in the good evening everyone in the red Tony
reads you read, Tony read bier following the news that's
right shape or no sortage of things to talk about?
Speaker 2 (00:15):
What did read? What will? This is a reality. We
simply have to step by me, read.
Speaker 1 (00:23):
Me, read, Let's go ahead and kids started.
Speaker 2 (00:31):
At thirty eight, I thought I found my forever job
until I was told I need to do more, and
that just shook me to the core. So what do
you do when the career you thought you were going
to have forever turns out to be very uncertain? Let's
get at it. One are the dangers that happens that
over time, as you move through your profession. If you're lucky,
you may find yourself in what I call a comfortable job,
(00:53):
one that's stable, one that gives you the support you need,
one that satisfies all of your financial requirements as well
as your cultural vironments. And all of a sudden, you
may find yourself believing you have now acquired your dream job.
That means a job that's going to allow you to
do all the things that you want to do during
your personal life and your professional life during the course
of your employment there and as such, because you've just
(01:14):
decided decided this is your dream job. You are not
taking any actions to do anything more than to do
everything possible to stay at that job as long as possible.
And for me, I found myself in that same spot
when I was around thirty eight years old. I thought
I was in a position where I believed that I
was at a dream job, that I was at a
job that I was going to be at for the
remainder of my career. I had been there about five
(01:35):
years and they literally supported me in all of my endeavors,
not only inside projects but outside projects as well as
providing a support network for me with my personal activities
as well as professional And there's nothing wrong with having
a dream job, and there's nothing wrong if you believe
you have a dream job. But there is a problem
if there's a turn you didn't expect. In my case,
(01:56):
it was being told after working for a firm, that
I was needed to do more in order to demonstrate
that I could go up in a higher position within
the company. Now, just merely being told to do more
and of itself, is not problematic. The problem within this
particular instance is that up to that point I was
instructed and provided information indicating that I had been doing
everything I needed to do to evolve accordingly. But now,
(02:18):
for the very first time, I was being told that
I hadn't done enough, even though I was under the
impression based on information I received that I hadn't done enough.
And now I'm being told that I needed to do
more in order to be able to get to the
next level internally within the organization. This concept of doing
more without any clear cut direction in terms of specified goals,
specified target objectives, things of that nature, created a measure
(02:42):
of uncertainty that I had never experienced during the time
that I had been there. So now I found myself
in this unique position of starting to realize that maybe
the company that I was working for, the firm I
was working for the long term commitment may not have
necessarily included me in that calculation. So now I found
myself with a really difficult challenge because I was at
(03:02):
a company who had been loyal and supportive of me
for this entire time period, but I was now facing
the fact that I was comparing the loyalty to the
realization that I needed to now not look at this
place as a place that I was going to be
at for the long haul and wondering what does that
mean for me if I choose to endeavor to try
to stay longer, or if I needed to look in
a different direction. This is where you get to what
(03:23):
I call the crossroad decision, because you're not just balancing
your own decision, you're looking at everything in its totality.
For me, I had to decide did I want to
stay and hope that everything that I was doing going
for would get me to the desired direction, or did
I want to start seeking other opportunity outside with the
uncertainty of whether I would find a place that was
(03:44):
similarly situated to where I was at, or if I
needed to entertain the lot of going on my own.
And it wasn't just merely focusing on what my next
professional objectives were. I still had a lot of other
things to take consideration as well. I had a card note,
I had a mortgage, I was married. I had all
these responsibilities that I had that were directly tied to
the job that I currently had, and so now I
(04:05):
was looking at possibly disrupting that all together, and I
didn't know what that would mean going forward. But the
hardest part is when you have all these responsibilities, it
sometimes makes you forget about how you manage to get
to this point to begin with. In other words, for
someone like myself, I had made career pivots before. This
wasn't a newer phenomenon, so I had a proven track
record of pivoting and being able to do so. But
(04:27):
the difficult thing I faced was that this part of
my life, as I was heading to thirty eight thirty
nine years of age, I didn't think I necessarily had
to make that pivot anymore. I was yearning to be
in a position where if I had to evolve, it
would happen organically internally at one place, and not me
having to physically go do something else. For me, the
decision was to start my own firm, and it wasn't
(04:49):
an easy one. It's what you have to call, ultimately
the leap of faith because I had no idea what
to expect. I had never run my own business before.
I was starting a new business with nobody at all.
Literally was taking advantage of opportunities that some of my
colleagues had provided to me, as well as referrals as
well as using their office space, and I still had
to be mindful of all my financial responsibilities, which included
(05:11):
a mortgage, which included the car, node which included bills.
All of these things, and even though I had my
wife who was also working that provided a measure of
comfort as well. The reality is is that these things
didn't go away just because I no longer was working
for my prior firm and I had now created my own.
But fortunately, two years afterwards, I was still going strong,
and I would remain strong for the next seven to
(05:33):
eight years. And it was this resiliency that helped me
feel more comfortable with the reality that I had made
the right decision. So by the time I had turned forty,
it did not feel like I had taken a step back.
I had just moved in a different direction to build
upon my skill sets and build upon my ability to
do things I had to anticipated. So what did I
(05:53):
learn when I learned that skills are transferable, So never
underestimate yourself. A lot of times what happens is that
you I think that the only person that truly values
your skills is the company that you work for, because
they're u lizing your skills to do something for them.
So there's a natural inclination to think that only your
job will pay for or value the skills that you
have when you don't realize that there are plenty of
(06:14):
people out there and opportunities out there that will take
advantage of those skills if you put yourself on the
right platform to be able to allow them to take
advantage of them. Two, don't fall into the cruise control
or your dream job. That's one of the hardest thing
to do because a lot of us crave stability, and
there's nothing wrong with that. A lot of us crave comfort,
nothing wrong with that as well. But the danger that
sometimes happens is that when you put your hands and
(06:34):
your livelihood and your future into the hands of one
specific group of individuals with the thought that they are
going to create this environment that's going to stay with
you for a particular period of time, there's always the
potential that something could happen to that job that could
shake or undermine exactly what it is that you value
in terms of stability. Third, and finally, crossroads are opportunity
(06:56):
for growth. A lot of times what happens is that
because we stay so laser folks on doing what we
do on a day to day basis, taking advantage of
the fact that we have an employer that's paying for
us to do certain things that we don't realize that.
One of the great things that may be kind of
tough things that comes from being at a crossroads that
forces you to look at things differently is that it
forces you to also grow. When you are now in
(07:17):
a position where you start to realize that your current
circumstances may change, whether it be because you're going to
have to change it or somebody's gonna have to change
it for you, you may find that this might be the
best time to start exploring skill set that you didn't
even realize that you had, or more importantly, skills that
you didn't fully maximize until put in a position where
you had to do so. I realized I was built
for this, and so are you. A lot of times
(07:39):
it takes being put in these positions to show you
and remind you that you are the person that got
to where you are today because of how resilient you are.
And never let the fact that you have been in
a position where you've been kind of on cruise control
have you doubting all of the energy that you put
into it gets you to that point. If you're at
a crossroads. Just remember three things. Trust your decision, trust
(08:03):
your resilience, and recognize you can. You will never go
wrong betting on yourself.
Speaker 1 (08:09):
M m hmmmmmm hmm
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