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25 Questions To Help You Get Unstuck

25 Questions To Help You Get Unstuck

Released Thursday, 7th December 2023
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25 Questions To Help You Get Unstuck

25 Questions To Help You Get Unstuck

25 Questions To Help You Get Unstuck

25 Questions To Help You Get Unstuck

Thursday, 7th December 2023
Good episode? Give it some love!
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Episode Transcript

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0:00

This episode is brought to you by Shopify. Shopify

0:02

is there to help you grow. Whether

0:04

you're selling shipping supplies or promoting

0:06

productivity programs, Shopify helps you sell

0:08

everywhere from their all-in-one e-commerce platform

0:10

to their in-person POS system. Sign

0:12

up for a $1 per

0:14

month trial period at shopify.com/accidentalcreatable. This episode

0:16

is brought to you by Indeed. We're

0:19

driven by the search for better, but

0:21

when it comes to hiring, the best

0:23

way to search for a candidate isn't

0:25

to search at all. Don't search, match

0:27

with Indeed. Just go to

0:30

indeed.com/creative right now. Need to hire?

0:32

You need Indeed. Hey

0:34

everyone, welcome to the show. My

0:41

name is Todd Henry. I am your

0:43

host. I'm also the author of several

0:45

books, including The Accidental Creative, Die Empty,

0:48

Hurting Tigers, and Daily Creative,

0:50

which is a daily reader for creative

0:52

professionals. On

0:54

today's episode, we're gonna replay something that I did in

0:56

2018. It's called 25

0:59

Questions to Help You Get Unstuck. Sometimes

1:02

when we're stuck, it's not because we don't

1:04

understand the problem. It's not always because we

1:06

don't have what we need in order to

1:08

solve the problem. Sometimes it's because

1:10

we're overlooking something, there's something obvious in front

1:12

of us, there's an impediment or a roadblock

1:14

or an assumption that we're making that's

1:17

keeping us from seeing things clearly as

1:19

they are. And so a

1:22

really well-timed, precise question can

1:24

sometimes unlock new

1:26

insights that were previously obscured.

1:29

So today's episode is very simply just

1:31

25 questions to

1:33

help you get unstuck. Hope you find

1:35

it helpful. And here is

1:38

the episode from 2018. Enjoy.

1:45

And speaking of stuck, today's episode is gonna

1:47

be all about how to get unstuck. No

1:50

matter how talented you are, we hear all the time people

1:52

say things like, well, there's no such thing as writer's block,

1:55

right? Or there's no such thing as creative block. Well, to

1:57

some degree, I understand that sentiment. I get

1:59

that. sometimes we use creative block

2:02

as an excuse. We

2:04

use it as sort of a

2:06

self-imposed barrier to prevent us from

2:08

having to take risks, prevent

2:10

us from having to leap out into the unknown.

2:12

The reality is that there are

2:15

some times when maybe we're stuck

2:17

because we haven't defined a problem

2:19

effectively or because we're not thinking

2:21

about the problem appropriately. And so

2:24

today's episode is going to offer

2:26

up 25 questions, questions

2:29

you can ask to get unstuck. All right,

2:31

it's bound to happen sooner or later. No

2:33

matter how skilled you are, no matter how

2:35

well prepared you are, inevitably

2:37

you're gonna find yourself stuck on a

2:40

tough problem with no clear path forward.

2:42

It's just the nature of doing creative work.

2:46

And it's tempting in these circumstances to keep

2:48

your nose down, just to continue cranking on

2:50

the problem, to stay myopically focused on what

2:52

you've been doing. The problem with this method

2:54

is that you may be digging yourself deeper

2:56

into an existing rut. at

2:59

the ready to help you reframe, shift,

3:02

or view the problem through a different window.

3:04

So I'm gonna share with you

3:06

a set of questions that have been used

3:08

in various situations to jog creative thoughts and

3:10

to help you think differently about stubborn problems.

3:12

And these questions can be used on your

3:14

own, but they're especially valuable if you use

3:16

them with your team. Now

3:18

at first glance, some of the questions might seem too

3:21

simple to be of value, right? So I just wanna

3:23

warn you in advance that some of these questions might

3:25

elicit a hearty eye roll. And

3:28

that's okay, because sometimes, even

3:31

some of the most simple tools

3:33

and tactics, if used appropriately, can

3:35

open up entirely new pathways of

3:38

exploration. Give it about 15 minutes of thought

3:40

and discussion, you might find that

3:42

some of these very simple questions lead to a

3:44

surprising level of awareness and potential new paths to

3:47

explore. So we have to be willing to immerse

3:49

ourselves in the process in order to get to

3:51

the deeply valuable ideas that reside just on the

3:53

other side of stasis. Again, if

3:55

you wanna download a worksheet with these questions,

3:57

just go to. little

4:01

creative.com/unstuck. It's

4:05

accidentalcreative.com/unstuck and you can download a worksheet that

4:07

you can use as a reference tool. Alright

4:09

here are 25 questions, 25 of

4:11

them that you can ask to

4:13

help you get unstuck. So if you're working

4:16

on a problem right now, if there's some

4:18

particular project that you're stuck on or that

4:20

you're having difficulty gaining traction on, I want

4:23

you to think about the project through the

4:25

lens of these questions as I discuss each

4:27

one. Okay number one, is

4:29

an assumption in the way. Alright

4:31

sometimes when we're really good at what we do, it's

4:34

easy to make assumptions about what is and

4:36

what isn't possible, what we can and what

4:38

we can't do because we've done it so

4:40

many times before but these are simply asumptive

4:42

ruts. So what are we assuming to be

4:44

true and what are we assuming to be

4:46

false are really valuable questions to ask if

4:48

you feel stuck. Now a lot

4:50

of things that come out of your mouth might be you know

4:53

might be valid assumptions but you might discover

4:55

that there's an assumption you're making that is

4:57

invalid. So what are we assuming to be

4:59

true, what are we assuming to be false

5:01

and what if they weren't? This

5:03

is a really valuable tool that you can

5:06

ask to get unstuck. So I encourage you

5:08

to ask that question. Number

5:10

two, what is the worst case

5:12

scenario? Sometimes we're stuck because

5:14

we're afraid of the consequences, we're afraid of

5:16

what might happen if we fail. So it

5:18

helps to envision the worst case

5:21

scenario. What's the worst case scenario if we

5:23

fail here? You know and

5:25

often we discover that the worst case scenario

5:27

really isn't as bad as we thought. A

5:29

lot of times the damage that's inflicted is

5:31

more psychological than actual. I'm afraid of my

5:33

reputation being tarnished, right? I'm afraid of how

5:35

people might look at me. I'm afraid of

5:37

a lot of other things that aren't

5:40

real consequences, they are

5:42

illusory consequences or psychological

5:44

consequences but not actual

5:47

consequences. So I encourage

5:49

you to ask what's the worst case scenario. The third

5:51

is what could I do the opposite? Okay

5:54

so I have a way that I normally approach the

5:56

work, I have a way that I normally tackle this

5:58

problem. Could I do the opposite? What if I... try

6:00

the entirely opposite approach, what would the

6:02

opposite approach be? Explore that.

6:04

Use it as a thought experiment, as

6:06

a way to get unstuck. How

6:10

can I thrill the end user?

6:13

Sometimes we're stuck because we

6:17

feel like we're being asked to do things that don't

6:19

really excite us and we don't really think are going

6:21

to excite the end user. If you step back for

6:23

a minute and you say, how can I thrill the

6:26

end user? What would it look like if there were

6:28

no resources as a constraint? How could I thrill the

6:32

end user with this? What would we do? What would

6:34

I do in that case? That's a great

6:36

fourth question. Number five, what

6:38

am I afraid of? What

6:41

is it that I fear might

6:43

happen if I take a

6:45

creative risk with this? It could be fear

6:47

of failure, but it also could be fear

6:49

of success, quite frankly. I know that if

6:52

I succeed, I'm going to have to continue

6:54

to sustain this pace forever. My expectations,

6:56

the bar for me, are going

6:58

to be raised moving forward. I

7:00

know that I'm going to have

7:02

to sustain this

7:04

pace. Am I afraid

7:07

of that? Or am I afraid of failure? Am I afraid of

7:09

what other people might think of me? What am I afraid of?

7:12

Could that be contributing to me being stuck? Number

7:14

six, do I understand why?

7:17

Sometimes the reason we get stuck is because we don't

7:19

understand the why behind the

7:21

what. We don't understand the core reason that

7:24

we're being asked to do the work. Highly

7:26

talented creative people struggle to do work if

7:28

they don't understand why they're being asked to

7:30

do it. They need to understand the deeper

7:32

patterns, the deeper themes. Ask yourself, do I

7:35

understand why? If not, maybe you need to

7:37

seek out that why. Maybe that's the reason

7:39

that you're stuck because you don't understand why

7:41

you're being asked to do what you're being

7:43

asked to do. Number

7:45

seven, where else has something similar

7:48

been done? Are there

7:50

any parallels? Is there any place out there that

7:52

you've seen something similar to what you're

7:54

working on right now? And could you apply some of

7:56

what you see out there to the

7:58

work in front of you? Number

8:01

eight, what is expected and

8:04

why? Sometimes the reason

8:06

we're stuck is because we don't understand

8:08

the expectations. We really, we're trying to

8:10

do something that we don't really understand.

8:12

We're shooting at a moving target because

8:14

we don't have clarity around what we're

8:17

supposed to do. So do I understand

8:19

my expectations and why are those the

8:21

expectations? And if you don't clearly understand

8:23

the expectations, that's a failure of leadership

8:25

and I address that in herding tigers.

8:28

I address the importance of setting clear

8:30

expectations for the team as a way

8:32

to create stability. But if

8:34

you don't understand the expectations, you need to seek

8:36

them out. So what's expected of me and why?

8:39

Number nine, who has

8:41

something to lose? Okay, sometimes

8:44

we're stuck because we're afraid on behalf

8:46

of someone else. Is there someone else

8:48

who has something to lose in this

8:50

project? And am I afraid to act

8:52

because I'm afraid of the consequences for

8:55

someone else? Who has something to lose

8:57

if this doesn't go right? And is

8:59

that contributing to my stuckness? Number

9:02

ten, this is one of my favorites, who

9:05

is the enemy and how do we foil them?

9:08

Sometimes we're stuck because we don't understand

9:10

what we're working against. We don't understand

9:12

the dynamics coming against us. So who

9:14

is actually the enemy here? And by

9:16

the way, it's not your competitor, it's

9:19

not the other company that produces a

9:21

similar product. That's not who it is.

9:23

The enemy is some force that you're

9:25

coming against in creating the work.

9:28

So if you're designing, you know,

9:31

branding for a new laundry detergent, well

9:33

what is really the enemy there that

9:36

you're fighting against? Right? Who are you really

9:38

coming against? It's not girt

9:40

and grime and it's not the

9:42

opposing company's laundry detergent. You

9:44

know, that's not what you're talking about.

9:46

What are you talking about? Really what

9:48

you're coming against is, you know, all

9:50

of the time that's wasted when you

9:52

have to rewash things, right? You're coming

9:54

against complexity in the packaging. You're coming

9:56

against all of these things. So what

9:59

are you coming... Against and who is

10:01

the enemy? How do you foil that enemy?

10:03

What are the forces working against you and

10:05

how do you for them number? Who

10:08

could solve this problem with ease and how

10:11

okay, so? Imagine that you

10:13

could draw upon the resources of anybody

10:16

in the world Anybody

10:18

throughout history that has there's

10:20

a brilliant creative problem solver Who

10:23

who could solve this problem with ease

10:25

and how might they approach this problem?

10:27

Right so how would they so get inside

10:29

their mind and ask how might they approach

10:31

this problem differently from the way that we

10:33

approach? This problem, and how would they do

10:36

it number 12? How would

10:38

my favorite superhero do it? Hey, so if

10:40

you get called upon Superman or Aquaman Aquaman

10:42

is Aquaman really anybody favorite super? Okay, maybe

10:44

it's my favorite superhero growing up Which is

10:46

really really weird and retrospect if you could

10:49

draw upon your favorite superhero What power would

10:51

they employ to solve this problem, and how

10:53

might they do it or? Another

10:56

13 that was very similar question. How

10:58

might my favorite movie character solve this

11:00

problem? Okay, so you're drawing upon your

11:02

favorite movie character. How might they solve

11:04

this problem number 14? Okay,

11:06

those are all kind of very similar questions number

11:08

14 could I change the

11:10

medium? Could I change

11:12

the medium sometimes we're stuck because the

11:14

container that we're filling is a

11:17

container that we're bored with or a container that

11:19

We know intuitively doesn't really match the kind of

11:21

work that we're trying to do so could I

11:23

change the medium? Is there a

11:25

way that I could do this in a different

11:28

format that might interact with people in a different

11:30

way? And how might that unlock new ideas for

11:32

expressing whatever it is? I'm trying to communicate okay

11:34

So could I change the medium number 15 could

11:37

I ask the question differently? Sometimes

11:39

we're stuck because we're asking the wrong question

11:41

We're asking questions that don't really get to

11:43

the heart of the matter and we know

11:45

that intuitively We know that we're not really

11:48

asking the right question That's really difficult for

11:50

us to reframe the question so

11:52

could I ask the question differently try

11:54

to reframe? The problem that you're solving

11:57

number 16 how with a third

11:59

grader of? approach this problem. This

12:02

is a really great one because if you

12:04

didn't have all of the residue and the

12:06

baggage and all the psychological stuff bouncing around

12:09

inside your head, all of the existing fears

12:12

and inhibitions and all of the things

12:14

bouncing around in your head, how would

12:16

you solve this problem? If

12:19

you were completely naive, if you walked into the problem

12:21

fresh, you had no clue what was going on, how

12:23

would you solve the problem? How would a third grader

12:25

approach this problem? Try to be

12:27

completely naive, ask stupid questions.

12:30

How would a third grader solve this problem? Number

12:33

17, what question do I need

12:35

to answer first? This

12:37

is a really good one as well because

12:39

sometimes we're trying to answer a question or

12:41

solve a problem, but we haven't answered a

12:43

more primal question. The reason that

12:46

we're stuck is because there's something more rudimentary that we

12:48

need to answer before we can get around to answering

12:50

the question that we're trying to answer with our current

12:52

work. What question do I need to answer first? Is

12:56

there something that I don't know that I need to know

12:58

in order to be able to get moving on what I'm

13:00

doing? Number 18, is there a

13:02

resource that I'm lacking? Is

13:04

there something I don't have in order to be

13:06

able to tackle this problem? Now, by the way,

13:09

this doesn't mean go out and buy new gear,

13:11

go out and buy new equipment because sometimes that

13:13

can be a distraction. If I only had the

13:15

right gear, I could write better or I could

13:18

make better music or I could design better. I

13:20

mean, sometimes it's reality, but

13:22

often that's a distraction. But is there a

13:24

resource I'm lacking? Is there some

13:26

knowledge I don't have? Is there a conversation I

13:29

need to have? Is there some tool that

13:31

I don't have that would help me attack this

13:33

problem more? Is there a resource I'm lacking? Number

13:35

19, how would I describe the

13:37

problem in three words? Sometimes

13:40

we make things too complicated and

13:42

we get stuck because there's unnecessary

13:44

complexity in how we're defining the problem.

13:46

How would I describe this problem in three words? If

13:48

I only had three words, what would

13:50

I do to define it? And how can

13:53

I simplify then how I define the problem so

13:55

it makes it easier to attack? Number

13:57

20, are there

13:59

sub-problems? to the main problem. Sort

14:02

of along the same theme of unnecessary complexity,

14:04

sometimes we're trying to tack too many

14:06

problems together. We're squeezing a bunch

14:08

of problems together into one problem. And the

14:10

reason we're stuck is because there are too

14:12

many sub-problems that need to be solved within

14:14

that main problem. So can you parse out

14:17

the project you're working on into sub-problems

14:19

that can be attacked individually and strategically?

14:22

You might be stuck because it's just simply

14:24

unnecessarily complex. There are too many things you're

14:26

trying to tackle all at once. Number

14:29

21, what's the world

14:31

like once the problem is solved? So

14:34

imagine that you have solved the problem.

14:37

Everything goes as planned. Everything

14:39

is perfect. What does it

14:41

look like after the problem is solved? And then once

14:43

you've figured out that ideal end state, you can work

14:45

your way backward. And sometimes what you can say, okay,

14:47

well, what has to happen in order to get there?

14:49

Okay, well, then what has to happen in order to

14:51

get there? Okay, well, then what has to happen in

14:53

order to get there? And you kind of work your

14:55

way back. This is a technique that's often called backcasting.

14:58

And it allows you to sequentially

15:00

work your way backward from an ideal end state

15:02

and figure out what needs to happen in order

15:04

to get there. So what does the

15:06

world look like once the problem is solved? This

15:12

episode is brought to you by Indeed. We're driven

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accidental creative. Number

18:03

22, who can I call

18:05

for help? Okay. Again,

18:07

creative work often is accomplished in isolation. We

18:10

do it on our own. We do it

18:12

in our office and we're just sitting there

18:14

and we're thinking and we don't get outside

18:17

of our own mind. We don't leverage other

18:19

people's experiences and perspectives and ideas. So

18:22

is there someone that you could call, not

18:24

because they're an expert on the problem, but

18:26

just to kind of jog new kinds of

18:28

questions. They might ask really naive questions and

18:30

that's great because it pushes you outside of

18:32

where you're currently looking. So who can

18:34

I call for help? Number 23,

18:37

can I create a metaphor for

18:39

the problem? Can

18:42

I create a metaphor? Is there

18:44

something that is kind of like

18:46

this or can I envision some

18:48

abstract way of envisioning this problem

18:50

that will help me think about

18:52

it from a more conceptual

18:54

standpoint? Sometimes we're too in the weeds. We're

18:56

too experienced. That's the problem. We're too experienced

18:59

and so we're too in the weeds and

19:01

we're looking at the problem too closely. It

19:03

helps to step back, create a metaphor, something

19:06

abstract that can help us

19:08

think differently about the problem, to

19:10

play with it, build a model of the

19:12

problem that we can play with that helps

19:15

us to think about the problem differently. Number

19:17

24, how would I start over? Sometimes

19:20

we fall prey to the sunk cost fallacy. We've

19:22

put so much effort and work into a problem,

19:24

into solving a problem or doing a project that

19:27

we feel like we have to continue on the

19:30

path we've been on. The reality is sometimes it's

19:32

better if we just blow everything up and start

19:34

over again. So if you had to

19:36

do that, would you do it the same way that

19:38

you're currently doing it? How would you start over if

19:40

you had to? It's a great way to get unstuck.

19:44

Number 25, what's the

19:46

primary block and why? Sometimes

19:50

you just need to ask yourself, what

19:52

is really in my way? What is

19:55

the primary block that is

19:57

preventing me? What is it about this

19:59

problem that is... especially difficult

20:02

or is causing me to feel stuck?

20:04

What is that? I mean, really spend

20:07

some time considering that. That's question number

20:09

25. All right. When

20:12

working individually on a problem, write a question at the

20:14

top of a sheet of paper in a notebook and

20:16

spend about 15 minutes writing an answer to it. You'll

20:19

be surprised by what you write. And when working

20:21

in a group, you can pose one of these

20:23

25 questions to

20:25

the group and record the answers on the whiteboard

20:27

or in some visible place and see what patterns

20:29

emerge over the course of 15 minutes. Whatever

20:31

you do, don't just get embedded in a rut.

20:33

Don't stare at the problem. If you want to

20:35

think creatively, you have to explore the periphery of

20:38

your problem. You have to stay active. You have

20:40

to stay alert. And these 25 questions can help

20:42

you do that. Remember that your

20:44

best ideas will often come from

20:47

the least expected places. Hey,

20:51

thank you so much for listening. If you

20:53

enjoyed the show, please support the show by

20:55

buying one of my books. You can buy

20:57

them anywhere books are sold. I have books

20:59

for creative pros, for leaders of teams, or

21:01

for people who just want to get some clarity about

21:04

what they're doing with their life. You

21:06

can learn more at toddhenry.com/books or

21:08

just search Todd Henry wherever books

21:10

are sold. Also jump on

21:12

the weekly newsletter. You can

21:15

subscribe at toddhenry.com/subscribe. Remember

21:17

friends, cover bands don't change the world. Don't be a cover

21:19

band. You need to find your unique voice if you

21:21

want to thrive. We'll see you next time.

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