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May 1, 2025 19 mins

Do you feel like you’re working hard but hardly moving up the career ladder? Is success only achievable through promotion? What will give you satisfaction?

In this episode our host Iona Bain is joined by Helen Tupper, co-founder of Amazing If and co-author of The Squiggly Career, to explore why success doesn't always mean a straight line to the top.

They discuss how to rethink promotions, build confidence and find purpose in a working world that’s increasingly non-linear. You’ll learn how to identify your values, grow your network with purpose and create a career that works for you.

Whether you’re climbing, pivoting, or staying put in your career, there are so many ways you can rewrite the rules of your success.

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Iona and her guests share their own personal thoughts and opinions in this podcast. These might be different from L&G’s take on things. They give information for a UK audience that’s relevant at the time of recording.

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Iona Bain (00:01):
Hi, I am Iona Bain and welcome to A Little
Bit Richer, brought to you by L& G. Now there
can be pressure to get ahead in your career to earn
more money and push for promotions. We can see competition
from all angles and it can be hard to build
the confidence to succeed, but we might be thinking too
linear. So here today to talk us through why we
need to reconsider our career opportunities is Helen Tupper. Helen

(00:26):
and her co- founder Sarah Ellis started the award- winning
company, Amazing If. They work with companies like Microsoft, Levi's,
BBC, Danone, and Visa to support people with the skills
to succeed in a squiggly career. Together, they're the authors
of two Sunday Times bestsellers, The Squiggly Coach, and You
Coach You. And their TEDx Talk, The Best Career Path

(00:49):
Isn't Always a Straight Line has been watched by almost
2 million people. Welcome, Helen.

Helen Tupper (00:55):
Thank you so much.

Iona Bain (00:56):
My generation has often been told that if we work
hard, then we can achieve success by climbing that career
ladder. Is that true? And if not, why not?

Helen Tupper (01:09):
There's a few things to unpack there. So work hard,
achieve success. I think what we might need to challenge
is what success means. So what the career ladder has
presented is that success equals seniority. And the promise is
if you show up, you work hard, you'll go up
this mythical ladder and you'll be happy because success is
being senior and that's possible for everybody. And there are

(01:30):
two really big challenges with that assumption. So the first
is that everybody is motivated by becoming more senior, and
the second is that promotions are possible for everybody just
as a result of working hard. And the reality is
that people are motivated by different things. Some people want
to stay in the job that they're in and grow
in that job and feel a sense of achievement and
connection to the work that they already do. Some people

(01:53):
want to experiment and learn by developing in different directions,
and some people do want to become more senior, but
what we have created is a construct where that freedom
isn't really allowed. And so people feel like they're failing
if they want to stay where they are or they
feel like they're doing the development wrong if they want
to take a sideways move. And so we need to

(02:14):
redefine what career success looks like for people and make
different answers okay. And also presenting this idea of the
career ladder where promotions are possible for everybody also doesn't
reflect the reality. They just are not that many promotions for
people and so it's a bit of a false promise.

Iona Bain (02:31):
And so does this situation create that feeling within a
lot of people that they're not good enough? How important
is confidence in all this?

Helen Tupper (02:39):
Well, there are many moments that matter in careers, and
one of them are the conversations we have with people
about our development. So if you are my manager and
you are asking me, " Helen, where do you see yourself
in the next five years?" And I think, " Well, the
only acceptable answer is to become more senior."

Iona Bain (02:55):
It always feels like a trick question, doesn't it?

Helen Tupper (02:57):
It's a really ladderlike question and it creates quite a lot of pressure on
somebody to come up with the right answer. And I
think that is the moment where people's confidence gremlins grow.
So they might think, "Well, I don't really know what I
really want to do, but I feel like I have
to say something so that you think that I care
about my career and I'm being ambitious." Rather than a
confident conversation, which might sound like, " Actually there are quite

(03:20):
a few different opportunities I'm interested in. What's most important
to me is..." I'd love to talk to you about
where those learning opportunities might be. And these open curious
conversations unlock lots more opportunity, but they do require confidence
from the individual and slightly different questions in career conversations.

(03:42):
It works best when somebody's got self- awareness and confidence
in their career, but the conversations that they're having with
their managers and their mentors and people in positions of
influence are not ladderlike.

Iona Bain (03:54):
So what are the things that maybe we should be
thinking about a little bit more when we're having those conversations?

Helen Tupper (04:01):
There are some what we call squiggly swaps. So there
are ladderlike words that creep into conversations which will limit
people's development. So for example, a conversation centered on my
job title. Something that's much more squiggly is to talk
about talents. So where do I get my energy? What
do I want to be known for? How can I
use that more much bigger, better conversation? We talk about

(04:22):
talents. Talents take people a lot further than job titles
do. Next one would be about sort of levels. So
ladderlike conversations often about levels and grades, squiggly conversations center
much more on learning. What do you want to learn?
They center much more on growth. What does growth look
like for you over the next 12 months? You don't
have to have all the answers, but I don't want people

(04:44):
to have the answers because I want them to be
curious and open. Having that awareness about yourself and your
career means that you are not predetermining the conversation, which I think
when people go, " I want to get promoted." The conversation's
predetermined. And if that promotion isn't possible, the conversation doesn't go
much further.

Iona Bain (05:03):
There is a big challenge to this though, which is
that titles and levels and grades matter to a lot
of people because they bring more pay. And that is
incredibly important, especially right now where people feel that their
incomes really need to rise. So what would your response
to that be? How do we get people to think

(05:24):
about getting a good income but also learning more?

Helen Tupper (05:28):
So there's sort of a short- term, long- term payoff
thing going on here. So in the short term, I
might want a job that pays me more. So in the
short term, I think we just have to be a
bit careful of the assumption that the only way I'm
going to get paid more is to get promoted. So often
there is movement within a grade or a level. Sometimes
a horizontal move into another function can also unlock pay.

(05:51):
It doesn't always have to be promotion. So I would
explore that, I would get curious. The long term is
that it is likely that learning will unlock more opportunities for
your career. So you might think, " Well, how does learning
a new skill right now help me get paid more
next week?" It might not to be honest, but what
it will help you with is next year, the next

(06:13):
couple of years, you will have more roles that are
available to you. And the more choice you have, the
more control you have and the more you can push
for the pay that's important. So I do think you've
got to balance short- term conversations about pay progression and long-
term learning that will create dividends for your development in
other ways, 2, 3, 4 years hence.

Iona Bain (06:35):
Yes. It sounds like you're talking about an environment in
which people don't have to be loyal to their employer.
Do we need to be thinking a bit more sideways
in terms of looking at what's available elsewhere?

Helen Tupper (06:45):
I want everyone to have the freedom and flexibility to
develop in the direction that's right for them. We call
it squiggle and stay. So we want individuals to have
the awareness to work out what is the right direction
for me to develop and we want organizations to provide
more than promotions to make that possible. So I think
really, whether it's inside an organization or outside an organization,
I don't want people to feel stuck. I think the

(07:06):
power of the employer over the employee has changed. I
think people do have more choices now, but that only
comes when they take control. You have to invest in
your learning. It's what makes you valuable, it what makes you
remain relevant and resilient in your career. I think you
also just have to have that awareness and confidence in
talking about your career, in talking about your skills. That

(07:27):
is what gives you that choice and that control.

Iona Bain (07:29):
So who can we look to for support in developing
ourselves in our careers?

Helen Tupper (07:34):
So in ladderlike careers, we often look to our manager
as the guru of good advice, the gateway for our
growth. And what happens if you don't have a great
manager, suddenly development are very dependent on them and you're limited
as a result. So what we want to create is a
community around an individual's career. And this doesn't mean you
have to know everybody in the company. It doesn't mean

(07:55):
you need 10,000 connections on LinkedIn. I think there's a principle that's
really important when you're building a community and then practically
there's four people that matter most. So the principle is
this is not just about people knowing people. So it's
not about casual connections, but strong relationships are built on
help. And this matters because one, people enjoy helping people.

(08:17):
So if anyone's thinking, " Oh, I feel a bit awkward
about networking." Your brain quite likes helping people. It's called
the helpers high, makes us feel useful, valuable. So thinking
how can I help is a better way for me
to start building a relationship with somebody. It also results
in reciprocity. So when people feel like you've been helpful,
they want to help you in return. And that's not

(08:38):
always an immediate action. It could be a month or
two down the line when you get in touch with
someone, they're much more likely to respond to requests for
help, having built that reciprocity.

Iona Bain (08:46):
Enlighten self- interest.

Helen Tupper (08:48):
Exactly. And to be honest, it just feels good. Even if someone doesn't help
you back, does it really matter? If you've helped someone,
you feel good. I always think that is good enough. So
that's the principle. Just think how can I be helpful?
Now, there are four relationships in a career community that
make the biggest difference to someone's development. So the first
is the role of a mentor. A mentor is just
someone who has done what you want to do. They

(09:09):
don't have to be more senior than you, could be
a peer, anyone really. And what you benefit from with
a mentor is advice, you're borrowing their experience really. Just
start with a meeting. Now you might have a conversation,
there might be a connection and you might have a follow-
up meeting or it might evolve into something more meaningful
over time. But don't start with this needs to be
a two- year relationship with somebody because it's quite a

(09:29):
lot of pressure to put on someone you've not actually
spent any time with yet. The second one is peer
relationships. So if a mentor has done what you want
to do, a peer is somebody who's going through what you are
going through. There's often a lot of trust and support
in there. They are experiencing things at the same time.
So you can share learning with each other. Peers accelerate
your development. Third one is a sponsor. This is where I

(09:51):
often find the biggest gap in people's communities. So a
sponsor is somebody who's got access and influence over an
area you are interested in. So that could be a
project that you'd like to work on, could be a
position that you're interested in. And what they can do
if you build the right relationship with them is they
can advocate for you. And the fourth and final one
is a coach. So coaches are people who will ask

(10:14):
questions to unlock your thinking, but in the context of
your community, this doesn't have to be a professional coach.
I think it's easier to think who do I know
that has got a coaching approach? So two skills to
look out for here, the people who ask good questions
and also to be a good listener because coaches are
not there to give the answers, they're there to ask

(10:36):
the questions. You are the person doing the thinking, generating
your own answers and think it's who have I got
and who have I not? And just to keep coming
back to that question because we all have gaps. None
of them are perfect, but it just helps us to
prioritize the relationships we need to invest in. It's just
somebody who is non- judgmental, who doesn't try and switch

(10:58):
to their experience and go, " Oh, well when I was
in this situation..." Because that's more mental mode. The best
way that I've found people with coaching approaches have been
the people that when I worked with them, they asked
me questions that I found a bit uncomfortable. Like, " Helen, why
are you actually doing that? What's driving you?" And when
I worked with them, (inaudible) . We're just trying to
get it done. I don't want to think about this now that's too big

(11:20):
a question. But now I hold those people in my
mind because I know you are going to ask the
hard questions.

Iona Bain (11:27):
They're like a sounding board.

Helen Tupper (11:28):
They are good at holding pauses. They don't interrupt. That's what to look out for.

Iona Bain (11:33):
We all need people like that in our lives.

Helen Tupper (11:34):
We do.

Iona Bain (11:34):
That's so valuable. So when you are thinking about making
a pivot and going in this different direction, people will
fear that it will go wrong. And if it goes
wrong, maybe it's meant leaving a job that had a
lot of security and not being as financially stable and
having a more difficult time. What would your advice be

(11:56):
to those who are scared about making that next move?

Helen Tupper (11:58):
So there's this fear- based response to change and then
there is a very practical one of, "But what if I
don't enjoy it? And what if I am not good
at it? I've not done this before." So I think
there are two different things to work on here. So
the first one is caging confidence gremlins. And the second
one is trying to get some exposure and experience before
you make that move so that you mitigate the risk

(12:19):
of it going wrong. The confidence gremlin piece, a lot
of that is moving from limiting beliefs. Like, " What if
people don't like me in that team? If I fail,
I'm going to be a failure." To more limitless thinking.
To honest it sounds a little bit cheesy, but the
truth is that when our confidence gremlins are growing, they
tell us a really negative story that stops us taking

(12:41):
action. So when I say limitless beliefs, all I'm saying
is change the story. So if I do it and I
fail, at least I'm going to learn. And it is
having a statement that you can say to yourself that
gives you at least the confidence to take action. The
second bit is, " But I don't have experience. I don't
know anybody, it might not work." Here, I would say
building a bridge between where you are today and where

(13:04):
you want to get to is really important. And that do you know people
say, look before you leap. I think this more, the
learn before you leap. Could you shadow somebody? Could you
just get a mentor who tells you about a day
in their life? And the more data you have about
this move for your development, the better the decision you'll
make is and the more informed you'll feel.

Iona Bain (13:24):
I mean a lot of young professionals who feel very
disillusioned and trapped on the corporate career ladder because they
feel that they need to be at the level they're
at in order to afford the lifestyle, but they're not
particularly fulfilled. What would your advice be to anyone who
feels that they're trapped in that situation and there's nowhere

(13:44):
to go?

Helen Tupper (13:45):
It's really hard. We spend a lot of our time
at work and so to feel you're not having the
impact that you want and you're not enjoying what you're
doing, I think there are things that you can do
about it though. I always go back to it was
one of our squiggly skills, which is around values. So
forget job titles and forget the way you work, just
forget all that for a moment. Actually, you at a
very human individual level, what is it that motivates and

(14:07):
drives you? That's all the values are and everyone has
them and they're not things that change. They're pretty stable.
So when I do these exercises, I have four words
that always come out. So these are my values, freedom,
growth, energy, and achievement. That is what makes me me.
They'll be different to your answers, different to other people's answers.

Iona Bain (14:23):
That sounds pretty similar to mine.

Helen Tupper (14:26):
But do you know with values, even when you have the
same word, it can actually mean something different.

Iona Bain (14:30):
Very true.

Helen Tupper (14:30):
So my business partner who is very different, she has achievement.
Her definition of achievement is having one big win to
work towards. That's my idea of a nightmare. I don't
want one big win. My win is having lots of
wins to work on. So even the same word can
mean something different. But the point is when I'm feeling
a bit flat or a bit frustrated, it's often because

(14:52):
my values are not being fulfilled. I haven't got freedom.
I've got a micromanaging manager. And it really helps you
to think, what am I missing at the moment and
what could I do differently? And sometimes the answer is
actually not in work. So I have been in a
situation where I knew what my values were and I
was red and be greening them and there was quite
a lot of red on my freedom, growth, energy and

(15:13):
achievement. I want to do this, but I can't work
out in this organization at this time. How am I
supposed to get this stuff? But I was slightly stuck.
There were reasons that I was in that role that
I could not change immediately. And so what I did
was I found that fulfillment outside of work. So I
still concentrated on achieving inside of work, but these values
are not going anywhere. I'm not going to be happy in
my life if I haven't got these things somewhere. And

(15:35):
so I actually started a side project and these things
that I cared about, I found fulfillment somewhere else. And
then what happened over time is I worked through the
work issues. I stayed in the company that I was
in and I made some changes, but they didn't happen overnight.
But in the meantime, those things that mattered most to
me, I was still finding fulfillment. I also in the
company that I was in, tried to connect with people

(15:55):
outside of my role, make new relationships because that is
what unlocks opportunity.

Iona Bain (16:00):
Because not all of us can have the luxury of working
in jobs that give us lots and lots of fulfillment
and satisfaction all of the time. Sometimes it is a job
that will pay the bills and that's okay.

Helen Tupper (16:11):
What is important is that you understand, we talk about
using your values as a compass for your career. Let
that be the thing that guides you in what you do.

Iona Bain (16:20):
A lot of what you've talked about, it's not necessarily
about getting recognition, it's about what drives you and what
makes you feel satisfied. So how can we step out
of that need for recognition that we all have that
I also think maybe is a bit amplified by social media.

Helen Tupper (16:36):
So I think when you know what your values are
and you ground yourself in your values, you're less dependent on
validation. And obviously recognition is important, but I think you
also don't need to just rely on recognition. You can't
support yourself with reflection. So what have I done well
this week? Who have I made a difference to? What
am I proud of? Those sorts of questions, we have

(16:57):
an exercise which we call very small successes. So at the
end of every day, particularly if you're going through a knotty
moment, this can really help. Just take two weeks at
the end of every day, force yourself to reflect on
three things that you've done well that day. The first
one you'll find, you'll be like, " I went for a
lunch break." The first one might come-

Iona Bain (17:16):
Still a win.

Helen Tupper (17:17):
It's still a win. That is exactly it because when
work doesn't feel great, it is very hard for you
to see your wins. The point of this is to see the
very small successes. And if you can keep this up,
three successes a day for two weeks, you will have
42 small things that you have done well. But 42 things doesn't
seem so small. It starts to be more significant and

(17:39):
suddenly I'm less reliant. My manager's never going to tell
me 42 things I've done well in two weeks. That's
never going to happen. I might get one.

Iona Bain (17:46):
You have to tell yourself.

Helen Tupper (17:48):
That's it, you have to tell yourself and you don't
have to do this all the time. But I would say
in the hard moments, it is very helpful that you
reflect and recognize your own wins rather than relying on
other people to validate you.

Iona Bain (18:02):
So this has been really, really helpful, Helen. But finally,
what are your three tips to create a career that works for you?

Helen Tupper (18:09):
I think number one, confidence. I think confidence can help
you to be so brave about the things that you
do with your development or it can hold you back.
And I think if you can start to be aware
of what gremlins are getting in your way and start
to change the story that they're telling yourself, it makes
a massive difference to your development. Second is community. This is
very hard to do on your own. Building a community

(18:31):
will help you grow beyond where you are today. And
I think the third thing is don't wait for other
people to do things for you in your development. You'll
start to get frustrated. Create opportunities for yourself. They don't
have to be massive. They could just be, " I'm creating
by sharing an idea. I'm creating by putting a meeting
in place with somebody." Just think, " How can I create
more opportunities for myself this week?" And even if it's just

(18:54):
one thing, it's better than the person who's waiting for
the career conversation six months from now.

Iona Bain (18:59):
Wonderful. Thank you so much, Helen.

Helen Tupper (19:01):
My pleasure.

Iona Bain (19:03):
Helen, that was incredibly insightful and I think we're all
feeling a little bit squigglier now. So thank you very
much and thank you for listening. I would absolutely love
it if you could follow the podcast, leave us a
review, and that way you can help others get a
little bit richer too. Keep up with the show on
YouTube, TikTok, and Instagram at Legal and General. Until next time, see

(19:25):
you soon.
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