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You Know The Hard Thing You Need to Do Next - Here’s Why It’s Worth Doing Now

Summary

The episode examines the human tendency to avoid difficult tasks and seek shortcuts, particularly in professional contexts like software development and career advancement. Jonathan Cottrell argues that while finding workarounds can be temporarily effective, many meaningful goals require facing hard challenges directly—whether that’s developing deep technical skills, building relationships with colleagues, or addressing career transitions.

Cottrell identifies that procrastination often stems from our desire to preserve optionality and avoid committing to paths that require significant time and energy. He suggests that listeners identify specific hard tasks they’ve been avoiding—such as improving relationships with bosses, developing technical expertise through practice, or having difficult conversations—and recognize that these obstacles will continue to resurface until addressed.

A key insight is that the decision to undertake a hard task is often more difficult than the task itself, because it requires closing off alternative pathways and accepting the investment required. Cottrell encourages listeners to choose one hard thing from their list and commit to taking the first step, while acknowledging that initial motivation won’t sustain them through the inevitable challenges and setbacks.

The episode concludes with practical advice: rather than relying on temporary enthusiasm, listeners should reconnect with their core motivations when facing difficulties. By understanding why a particular hard task matters for their career growth, skill development, or personal fulfillment, they can maintain commitment through awkward conversations, failed attempts, and other obstacles that make hard tasks challenging.

Topic Timeline

  • 00:00:16 — Introduction to the hard things we avoid — Jonathan introduces the concept of tasks we know we need to do but keep putting off. He distinguishes these from ordinary difficult tasks, describing them as persistent problems that won’t disappear on their own. The discussion frames this avoidance as a human tendency rather than laziness, stemming from our desire to reduce cognitive load and accomplish more quickly.
  • 00:01:39 — The limitations of shortcuts and workarounds — The episode explores how successfully finding shortcuts for some problems creates a reinforcing loop where we start looking for shortcuts everywhere. However, certain aspects of careers, relationships, and skill development require difficult, messy, slow work that involves failure and repetition. These are the hard things we must eventually face rather than avoid.
  • 00:03:04 — Examples of hard things in professional contexts — Specific examples are provided of hard tasks developers might avoid: developing domain knowledge for authority in their role, building relationships with coworkers or managers, or addressing conflicts. The discussion emphasizes that even without active conflict, the temptation to avoid relationship-building persists because it’s uncomfortable work that doesn’t feel immediately necessary.
  • 00:05:05 — The hard path to skill mastery — Using Python development as an example, Jonathan contrasts the desire for easy learning methods (books, tutorials, AI) with the reality that true mastery comes from repeated practice, building challenging projects, and receiving feedback. He notes that great engineers typically attribute their skills to extensive building and critique rather than shortcuts.
  • 00:07:18 — Why we avoid hard things — The episode examines common excuses for avoidance: being ‘too busy’ or believing there might be an easier way. Our minds race to find alternatives because committing to a hard path means giving up optionality and accepting significant time and energy investment. This psychological resistance makes even the decision to start difficult.
  • 00:09:47 — The pain of closing optionality — A core insight emerges: choosing hard tasks is difficult because it means opting out of all alternative pathways. This loss of optionality is psychologically painful and explains why starting hard things feels so challenging. The decision itself represents a commitment that feels restrictive compared to keeping all options open.
  • 00:10:47 — Moving beyond temporary motivation — Jonathan warns that initial enthusiasm won’t sustain through the actual difficulties of hard tasks. When relationships become awkward, conversations don’t go as planned, or setbacks occur, it’s easy to abandon the commitment. The solution is to reconnect with core motivations rather than relying on fleeting energy.

Episode Info

  • Podcast: Developer Tea
  • Author: Jonathan Cutrell
  • Category: Technology Business Careers Society & Culture
  • Published: 2025-12-02T10:00:00Z
  • Duration: 00:13:01

References

Podcast Info

Transcript

[00:00:00] Hey everyone and welcome to today’s episode of Developer Tea.

[00:00:09] My name is Jonathan Cottrell and my goal on this show is to help driven developers like

[00:00:13] you find clarity, perspective, and purpose in their careers.

[00:00:16] Today we’re talking about the thing you know you need to do.

[00:00:21] The thing that’s sitting in front of you that you’ve been putting off.

[00:00:24] I’m not just talking about the hard task in your current sprint, although that could

[00:00:31] fit this mold in some way.

[00:00:34] The thing that you know that you need to do, that you need to address, that’s not going

[00:00:40] to go away.

[00:00:42] The thing is that we often try to find ways around our hard problems.

[00:00:49] It’s not because we’re lazy, it’s because this is part of what it means to be a human.

[00:00:53] It works.

[00:00:54] We are looking for ways to reduce the load on our brains and get ahead.

[00:01:00] We want to get more done sooner.

[00:01:02] We want to get past our obstacles and accomplish things that matter more to us than getting

[00:01:07] through the obstacle.

[00:01:09] And sometimes this works, which is kind of a reinforcing loop.

[00:01:13] We can hack our way around a particular problem and not have to deal with the hard parts and

[00:01:21] then jump ahead.

[00:01:21] And so we start to model.

[00:01:24] More of our problems in this particular manner.

[00:01:28] We find shortcuts here and there, and therefore we start looking for shortcuts everywhere.

[00:01:34] And it becomes the way we imagine just accomplishing everything.

[00:01:39] But the truth is that there are aspects of your job.

[00:01:44] There are aspects of your life, of your relationships, of your career, of hobbies that require that

[00:01:54] you do something.

[00:01:55] That is difficult, that’s messy, that is slow, that is inefficient, that requires some deep

[00:02:03] level of thinking, something that you have very little skill in doing, that you have

[00:02:08] to try over and over and fail over and over at.

[00:02:13] These are the hard things that we have to face.

[00:02:18] And it’s very likely that you have a hard thing that you already know about that you’ve

[00:02:23] been trying to avoid.

[00:02:25] Now, not everything that we’re trying to avoid is worth doing.

[00:02:30] But many times the things that are worth doing are hard enough that we do try to avoid them.

[00:02:38] In other words, we procrastinate, we find reasons to do something else first.

[00:02:46] We imagine that we’re eventually going to strike gold and find another path to where

[00:02:51] we’re trying to go.

[00:02:52] But most of the time, that same obstacle, whatever it was the first time, is going to

[00:03:00] come up again and again and again.

[00:03:04] Whether that’s the domain knowledge that you need to be able to operate with some level

[00:03:09] of authority in your current role at your current company.

[00:03:13] Maybe it’s the relationships that you haven’t developed, that you know you need to develop,

[00:03:19] that you keep on running into problems.

[00:03:22] Maybe you have problems with a coworker on your team, or maybe your product manager.

[00:03:28] Maybe you and your boss have not really carved out any kind of personal connection yet.

[00:03:34] And you may not even have any conflict there, which is why it’s so tempting to kick the

[00:03:40] can, to not do the thing that you know needs to be done.

[00:03:44] The most important part is that hard thing that you’re procrastinating on.

[00:03:52] So, I want you to imagine that this is never going to go away.

[00:04:02] Try to figure out in your mind while you’re sitting here listening to this, write down

[00:04:06] two or three of these things that you know that’s something that if I were to have done

[00:04:13] it already, a problem would be removed from my path, or I will have grown in some significant

[00:04:20] way.

[00:04:21] If I would have repaired the relationship with my boss or deepened it, then maybe I

[00:04:28] wouldn’t be so afraid of losing my job, right?

[00:04:33] Or maybe I would feel more comfortable asking for an alternative position, maybe move to

[00:04:42] a different team if my boss and I were on better terms or if we were closer, right?

[00:04:47] So, thinking about the consequences of this.

[00:04:51] Because if you’re like most people, you’re trying to find a way to do that thing to get

[00:04:57] to that other team that doesn’t require you to go the hard path of improving your relationship

[00:05:03] with your boss, right?

[00:05:05] So similarly, if you want to become a great engineer, a great Python developer, for example,

[00:05:14] a lot of people want to read a book or a tutorial or find some kind of tool or even lean on a

[00:05:21] computer.

[00:05:22] They want AI to teach them more about Python.

[00:05:26] But the hard path is building things over and over.

[00:05:31] Building things over and over and over.

[00:05:35] Getting feedback from other engineers.

[00:05:38] Getting those reps of building things.

[00:05:41] And not just building things for the sake of building them, but building things that

[00:05:44] actually challenge you, that actually, you know, push you to put the things in practice.

[00:05:50] Right?

[00:05:51] That you’re learning.

[00:05:53] There is no easy button to become a great Python engineer.

[00:05:58] Ask any great Python engineer how they got there and I can almost guarantee you that

[00:06:04] they’re going to answer by saying, by building a lot of stuff and having other people tell

[00:06:09] me what was wrong with it.

[00:06:10] Or some form, some variation of that.

[00:06:14] And that’s true not just in Python, for just about any specific technology that you can

[00:06:20] find.

[00:06:21] So, instead of hacking your way into your next job, instead of figuring out how to keyword

[00:06:26] stuff your resume the perfect way, what is the hard thing that would help you more?

[00:06:35] The hard thing like developing a relationship with the recruiter at the company that you

[00:06:40] are thinking about moving to.

[00:06:44] What’s the hard thing that helps you start your own business?

[00:06:49] Or…

[00:06:50] What’s the hard thing that helps you, you know, move from being an individual contributor

[00:06:55] to a manager?

[00:06:57] What are the hard things standing in your way that if you were to have done them, if

[00:07:02] you could check off the box, you would.

[00:07:04] Right?

[00:07:05] If you could say, oh, yes, that’s behind me, then everything else becomes easier.

[00:07:12] Now, trying to answer the question, why haven’t you done that?

[00:07:18] Why haven’t you…

[00:07:20] taken most of your energy and put it towards the hard things that would actually move you

[00:07:25] forward?

[00:07:26] The majority of the time, the answer is because we think that there’s either we’re too busy,

[00:07:32] which is probably a lie, or we think that there may be an easier way.

[00:07:40] And so, our rat race in our mind is running on overdrive, trying to find a way around

[00:07:47] this thing.

[00:07:48] And…

[00:07:49] And the difficult answer is being honest about that and saying that your next step

[00:08:01] should be to give up on all of those alternate pathways that could be faster, that could

[00:08:08] be easier, that could be lower investment, right?

[00:08:13] And choose, make a decision to go with that hard path.

[00:08:17] So…

[00:08:18] It’s…

[00:08:19] It’s very uncomfortable to do this.

[00:08:22] In fact, I can show you how uncomfortable it is by asking you to do it right now.

[00:08:28] Pick one of those things on your list.

[00:08:30] It doesn’t have to be all three of them.

[00:08:32] That would be really difficult to do.

[00:08:34] Right?

[00:08:35] Just three, four, whatever you have written down.

[00:08:40] And make the commitment right now to do one of them.

[00:08:44] It’s going to be hard.

[00:08:45] It’s going to be really difficult.

[00:08:47] So…

[00:08:48] It’s going to be really difficult that I think most people listening to this right

[00:08:50] now will…

[00:08:52] May even pause this episode.

[00:08:54] It’s such a hard thing to do.

[00:08:57] Why is that?

[00:08:58] Why is it difficult to make the decision to do a hard thing?

[00:09:03] It’s not even the actual act of doing the hard thing.

[00:09:07] It’s the decision to do the hard thing.

[00:09:10] It’s because we’re giving up on all of these alternative pathways.

[00:09:15] We are letting those things go.

[00:09:17] Right?

[00:09:18] Which means that we’ve opted into something that’s going to take a significant amount

[00:09:24] of our time and energy and we’ve opted out of everything else.

[00:09:31] Choosing to cut off our optionality is painful.

[00:09:36] And this is one of the core reasons why doing hard things is hard to even start.

[00:09:43] Right?

[00:09:44] It’s hard to even start to make a decision.

[00:09:47] And do the thing that you know you need to do because you are choosing not to do a whole

[00:09:52] myriad of other things.

[00:09:54] You’re closing off your optionality.

[00:09:56] I can almost guarantee you that if you were to choose to do one of those things that you

[00:10:00] know you need to do, you will be better off for it.

[00:10:03] I’d encourage you to try it.

[00:10:05] I’d encourage you to write down that commitment.

[00:10:07] Go talk to your boss today.

[00:10:10] Make the…

[00:10:11] Make the…

[00:10:12] Whatever that next committed step is and then figure out what the first step is towards

[00:10:16] actually doing that hard thing.

[00:10:19] Take the first step.

[00:10:21] At the risk of sounding like a motivational speaker, this is actually one of the most

[00:10:25] difficult things to get motivated about.

[00:10:29] And so hopefully you’re listening to this.

[00:10:31] Hopefully you’re not hearing me trying to hype you up and have you just lean on the

[00:10:39] motivation feeling that you have right now, the energetic feeling that you might have

[00:10:44] hearing this.

[00:10:45] That won’t carry you through this.

[00:10:47] It won’t carry you through the obstacle.

[00:10:50] It may carry you through the first round of combat with the obstacle, but it’s not going

[00:10:54] to carry you through when the hard parts start happening, when you start screwing up, when

[00:11:02] the relationship development is awkward, right?

[00:11:05] The conversations with your boss are awkward or they’re not going as expected or maybe

[00:11:10] your boss delays your one-on-one because he doesn’t quite have time for it.

[00:11:15] That’s when things get hard and it’s easy to throw in the towel and that’s when you

[00:11:20] have to come back to this episode and remind yourself that you may see an out in that moment.

[00:11:26] You may see, okay, I’m going to open my options back up again.

[00:11:30] I’m going to decommit.

[00:11:31] I’m going to move back away.

[00:11:32] I’m going to backpedal out of that and I’m going to see if I can figure out another way

[00:11:36] forward.

[00:11:37] And that’s almost always going to be a mistake, right?

[00:11:41] So come back to this episode.

[00:11:42] Listen to this again so that you can reinforce.

[00:11:45] Why you’re choosing to do this.

[00:11:48] What about that specific obstacle is going to carry you forward to the next place you

[00:11:53] want to be in your career, in your life, as an engineer, in your skill set, whatever those

[00:12:00] things are.

[00:12:01] If you can stay committed to that reason, that underlying reason why you’re doing it,

[00:12:05] your core motivation, then you’re more likely to stick with whatever that commitment is.

[00:12:10] Thank you so much for listening to today’s episode of Developer D.

[00:12:12] I hope you enjoyed this episode.

[00:12:14] I hope that…

[00:12:15] I hope that it was somehow enlightening for you.

[00:12:17] Maybe you haven’t thought about why, you know, what, what the relationship between you and

[00:12:23] the, the kind of avoidance mechanisms, why did those exist?

[00:12:27] You know, how should we listen to those things?

[00:12:30] Should we always do those things?

[00:12:32] Probably not, by the way.

[00:12:34] We didn’t dive into when your inner voice may be kind of leading you the wrong path,

[00:12:39] but, um, you know, it’s very likely that you have a very strong intuition.

[00:12:44] For some of you, it’s very likely that you have a very strong intuition.

[00:12:45] It’s something that needs to be done.

[00:12:46] That’s difficult, but it’s still worth doing.

[00:12:49] And I would encourage you to follow that.

[00:12:51] Thanks so much for listening.

[00:12:52] And until next time, enjoy your tea.

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