65. Why You Should Plan to Fail

The concept of planning to fail might have you feeling a little confused or resistant. None of us want to intentionally fail, of course, and my work often revolves around helping interior designers cultivate a more positive mindset around their business. This makes the idea of planning to fail seem contradictory, but stick with me.

Planning to fail isn’t about pessimistic thinking or being overly critical about how you can’t hit your goals. It’s about using the potential of failure as part of your planning process. Whether you use it in the context of your big-picture goal-setting or in your daily or weekly planning, planning to fail not only radically increases your chances of achieving your goal, but also improves your experience of pursuing it. 

Listen in this week to hear why planning to fail is the secret to creating success faster with increased enjoyment along the way. I’m highlighting how we unwittingly make the pursuit of our goals more stressful than necessary, why we don’t want to dwell on the obstacles we might face, and how to incorporate failing into your success plan.


I’m hosting a two-part goal-setting workshop at the end of January! Create Your 2024 Roadmap is where I’ll help you set your goal for the year and create a plan to help you achieve your big-picture goal. It’s only $87, including a guided planning session and a live coaching call with me, so sign up by clicking here.


What You’ll Discover from this Episode:

  • One of the biggest reasons designers fail at achieving their goals.

  • The power of elevating your experience of pursuing goals.

  • What it means to plan to fail.

  • How we unwittingly create internal suffering as we pursue goals.

  • Why planning to fail is the secret to creating more success and enjoyment of your goals.

  • How to use the concept of planning to fail in your favor.

Listen to the Full Episode:

Featured on the Show:


Full Episode Transcript:

Hey designer, you’re listening to episode 65. This is the one where I’m sharing why you should actually plan to fail in your interior design business, whether it’s as you pursue your big goals for the year or are just planning out your day. Come along with me as I share how to incorporate failing into your success plan.

Welcome to The Interior Design Business CEO, the only show for designers who are ready to confidently run and grow their businesses without the stress and anxiety. If you’re ready to develop a bigger vision for your interior design business, free up your time, and streamline your days for productivity and profit, you’re in the right place. I’m Desi Creswell, an award-winning interior designer and certified life and business coach. I help interior designers just like you stop feeling overwhelmed so they can build profitable businesses they love to run. Are you ready to confidently lead your business, clients, and projects? Let’s go.

Hello, designer. Welcome back to the podcast. I’m so glad to be here with you today. As you know if you’ve been listening sequentially, I recorded a lot of episodes in advance of the new year between me being off and my podcast team being off and here we are. This is my first episode back at my desk recording for you and it feels like just hopping back on a bike again.

We were in Costa Rica, as you know, for a couple of weeks. And now I’m staring out my window and seeing it is very snowy. But I just thought I’d share a little bit about what we did. It felt like such an adventure. The first part of the trip was on the beach where we’ve stayed before. But then we went to Corcovado Wilderness Lodge, which is a resort that runs up against Corcovado National Park, which is actually on Costa Rica’s Osa Peninsula.

And the only way to get to this lodge is by boat. So it was kind of a crazy adventure getting there. We had to drive quite a ways to this very tiny airport. We took a five seater plane, so it was my family and the pilot. I got to sit in the front and it was very cool to be in the co-pilot seat. And also I was just terrified to move the entire flight because I didn’t want to accidentally press something I wasn’t supposed to press. So I held very still for that hour that we were in flight.

And then we landed. We had to take another trip in a van. The lodge picked us up, took us to Drake’s Bay. So this is a very tiny little town. And then they got us on a boat where it was about a 40 minute boat ride to get over to the resort where then we got checked in and all of that, got the lay of the land, met our amazing guide. And it was such a cool experience.

I mean, it was really difficult to get to. So I don’t know that we’ll be going back anytime soon, but we did some incredible activities. We went snorkeling and actually saw a shark while we were out snorkeling. And everyone’s been asking me, well, were you afraid? And surprisingly not, I guess I was kind of just like if the person who’s leading this expedition is not worried, I’m not going to be worried and we’re just going to go with that.

And my husband and son went on a fishing expedition while my daughter and I stayed and had a leisurely morning. And they caught a tuna. My son, my 10-year-old actually caught a tuna, which was so exciting for him. And they made sashimi right there on the boat. So we’ve got this video my husband brought back of my son eating the sashimi from the tuna that he caught, which was super cool.

And also I’ve been telling people it kind of had the White Lotus vibes to it a little bit. It was more wilderness-y and definitely not as glamorous as the lodging in that White Lotus show. And for those of you who are not familiar with White Lotus, it’s like the one show that I’ve watched in the past two years, but it was so good. My husband got me hooked on it. And anyways, there’s kind of these groups of people that you’re following through the show and they’re all at this resort and their storylines interact with each other.

So anyways, that’s why I kind of thought this place had that going on because there were some other families there. We met this amazing family with older kids from Canada. And then we met this other family with kids that were similar in age to our kids and they were there from LA. So anyways, it was so fun, lots of adventures and we really had no idea what to expect going there.

And all that to say, it was a great experience and also happy to be home and hope you and your family had an incredible holiday season and are settling into this winter season.



Today, what I want to talk about is planning to fail. And if you just had a little bit of a reaction to me saying that, like, “Oh, that sounds awful,” just stick with me. One of the biggest reasons that I see designers fail at their goals is because they don’t plan for failure. What I mean by this is not having super pessimistic thinking and beating yourself up and being really critical about how you can never hit your goals.

But what I’m saying is use the potential for failure as part of your planning process and put it on the table as an option so that you can look at it. I’m going to talk specifically about goal setting when we’re talking about planning to fail, but know that this really applies to your daily or weekly planning, your health goals or habits you want to implement personally.

This is really a universal lesson of planning to fail and how it can support you in whatever it is you want to achieve. And it’s not only going to radically increase your chances of hitting a goal, it will also dramatically improve your experience of pursuing goals.

If you think about goal achievement, the moment you reach your goal, that is only a tiny fraction of your life. Every other moment that you have is in pursuit of the outcome or that goal. I was thinking about this over the weekend and how often we think that achieving the goal will make us feel good about ourselves.

And if you’ve been following along, it’s our thoughts that we have about ourselves when we achieve the goal that makes us feel good. And of course, we have experiences where we feel pride, we feel accomplishment, we feel excited when our goal is reached. But often, we think that along the way we have to feel bad and suffer in some way to pursue that good feeling that we associate with hitting the goal. And I want you to consider that maybe that’s not true.

I want you to consider that perhaps elevating your experience of pursuing goals, meaning feeling good along the way, and you’re going to feel better when you don’t make failure a problem. That is actually how you are going to get there, to your goal, whatever there is for you, faster and with more ease and with more enjoyment.

What I want you to hear right now is that planning to fail, even if it initially sounds off-putting, is actually the secret to creating more success and more enjoyment when it comes to goals because you can enjoy setting and achieving goals and the pursuit of the actions that are required in order to achieve that goal when you change your relationship to failure, and that includes planning to fail.

If you’re listening to this in real time and want to work with me on setting yourself up for success in the coming year, you have to join me in my upcoming goal-setting workshop, Create Your 2024 Roadmap. This is a two-part workshop. January 26th and February 2nd is when we’ll be meeting. And it’s an interactive workshop where you’ll not only learn my process for stress-free goals, you’ll be planning live on the call and getting my direct personalized feedback.

And you can ask questions and get that personalized support right from me. And of course, you’re going to learn so much from being in the community with your peers and hearing their questions and their a-has. You’re also going to be able to implement this concept of planning to fail in real time with me.

There will be replays, and while I’d love to have you there live, you can absolutely catch the replay and complete the process when it’s convenient for you. I know some of you are on the other side of the world, and the times I offer things are your middle of the night. Or maybe you already have meetings scheduled and it’s not going to be possible to make it live. But don’t let that be the reason why you don’t set yourself on this trajectory for your best year yet.

Create Your 2024 Roadmap is only $87. So it’s super accessible, especially for the level of support that you’re going to be able to get. The link to join us www.desicreswell.com/roadmap-2024, and of course, that will be in the show notes as well.

All right, let’s dive into this topic of planning to fail. When I’m talking about failure, I’m talking about it here really in broad strokes. Failure means something different to each and every one of us, but just for the sake of us all being on the same page, when I’m talking about failure today, what I’m meaning is you’re not hitting a specific revenue number you set, or maybe a certain number of clients, or you’re not completing a project you identified or an initiative you wanted to undertake.

Essentially, you’re not arriving at some set point or outcome that you determined for yourself in advance. Personally, I think we need to broaden our definition of success and failure for a variety of reasons, but that’s a whole other episode. For today, we’re just going to focus on you set an outcome that you wanted to achieve and you did not hit it. That’s the potential failure that we’re talking about and planning for.

And like I said, what I see is that most often is that failure, meaning you get to the end of that timeline that you gave yourself to achieve something specific, that fail happens because you didn’t plan for the failure. I think a lot of times we’re setting goals from a place of total optimism or fantasy. We have our most motivated self in mind, the one who always follows through, who always does what they say they’re going to do.

We’re thinking of times when the stars align perfectly. We show up perfectly. Other people do exactly what they’re supposed to do when they’re supposed to do it. We’re only thinking about when there’s a lull or quieter time, when we know there’s going to be maybe scads of open blocks where we can really dive in and focus.

And this is a little ironic because for so many of my clients, we work on shifting their mindset to a more positive place, reducing the negative chatter and the second guessing and the imposter syndrome. And we certainly don’t want to dwell in the negative. It’s very helpful and useful to shift to a more useful thinking process, and at the same time we also want to recognize that nothing ever goes exactly according to plan.

What I want you to consider is that it’s not supposed to. When we believe that it is supposed to happen, meaning you attaining that goal or you taking action in a certain way, when we believe it’s only supposed to happen in one very specific, linear way, we create a lot of internal suffering and then a lot of external chaos from the reactivity and the quitting. And the solution is thinking ahead to failure.

What I want you to do as you’re pursuing your 2024 goals is ask yourself, what could go wrong here? I’m going to repeat that again. What could go wrong? And then here’s the really important part, you have to answer your own question.

This is the difference between the negative type of thinking that’s going to send you into a downward spiral about how you’re not capable and how you’re not going to achieve your goal and how it’s never going to happen, and using planning to fail as a way to support yourself and set yourself up for success. We have to answer our own questions and see what those answers are.

In Create Your 2024 Roadmap, I’m going to encourage you to set a revenue goal for the year as your starting point. And then you’re going to identify quarterly projects and action items that are going to support that goal. And I’m going to use this as an example of how we can use planning to fail in our favor.

So let’s say you take my advice, you set your revenue goal for the year, and you identify that what could go wrong is that your current marketing strategy, or maybe lack of marketing strategy, isn’t calling in clients that have the higher level of scope or budget to support that revenue goal. Knowing that that could be a potential pitfall is really good to know because if you know that that’s going to be the thing that could mean you don’t reach your goal, now you get to decide what you want to do about it.

Or maybe you have plenty of best fit clients coming into your business to support the revenue goal. But the thing that could go wrong is that you continue to overwork and overextend and you’re burning out. And you’re going to be so burned out that you’re just going to want to abandon ship and it’s because you don’t have enough support in your business. Also good to know and good to be honest about because then you get to make an empowered decision about how you move forward.

If not having the right clients or not having enough hands on deck to hit your goal is the issue, now you can begin to solve for this ahead of time so you don’t get halfway through the year or even to the end of the year and go, why is this not working? Making it mean that you’re not capable of hitting your goal or just plain giving up. That’s not it at all, you just didn’t plan for the obstacles that might get in the way of you achieving the goal.

You can ask yourself what could go wrong and plan for that. And you can also learn to observe that internal narrative, which is something that I teach my clients to do so that you don’t have to stay in the negative thought loops if that’s where your brain is going. But you can actually gain some really useful insights from your worries and fears.

Instead of hiding from the things that could go wrong or trying to shove those thoughts away, what if you set your goals knowing exactly what could go wrong and then planning to solve for those ahead of time? What if you made those obstacles part of your plan to achieve the goal?

Often we unconsciously think that if we ignore the potential for failure, we can actually help prevent the failure as if, well, if we just shove it in that deep, dark closet and never open the door, then maybe we’ll never have to see it. But it’s actually the opposite. And when you put failure on the table right from the get-go, it doesn’t have to be as scary. The failures don’t have to seem like these insurmountable obstacles because you’re shedding light on them and deciding what to do with what was previously in the shadows.

I think this takes so much pressure off pursuing your goals because it changes your relationship to goals. Potential failure doesn’t mean you might potentially be a failure. When you accept that failure is a part of achieving your goals, failure becomes less of a personal attack on your worthiness or your capabilities, and just another thing to navigate.

Not to mention planning for failure is also such a huge time-saver. Think about all the time you might be spending procrastinating, trying to avoid failure. And this just isn’t even around goals, this could be around not picking the right selection for your client. If you just put failure on the table as an option, trusting that you’re capable of handling it, that you can be resourceful, that you can find solutions, you are going to be able to get and stay in motion with so much less friction and so much more ease.

And this is going to save you actual time during the day. And it’s going to mean that you’re going to be able to quickly recover from things when they don’t go as planned and achieve your goals potentially on a quicker timeline. Not that you need to achieve them on a quick timeline.

That’s not what I’m saying. But what I am saying is I want the time that you devote to moving the needle in your business to be actually used to make progress on your goals versus doing other things that aren’t moving the needle and are just detracting and adding to the mental drama.

I think probably most of us would say, yes, it’d be great if we set a goal and knew for sure we could hit it and the whole thing would be smooth sailing. But let’s be honest, this is just not how it goes. And I think there’s also an argument for why failure makes us stronger. It helps us evolve as the CEOs of our business. But again, that’s another podcast.

But this week, what I really want to encourage you to do is drop the resistance to failure and actually start planning for it. I highly encourage you to sign up for Create Your 2024 Roadmap. We are going to be able to work on this together. We can coach on all of those worries and fears about failure and plan for them together.

And we’re going to create a doable plan, one that allows for things to potentially shift, priorities to change, failure to happen. That’s going to get you to your 2024 goal. And you can implement this concept of planning to fail right alongside me and a group of peers. If you want to succeed at your 2024 goals, you don’t just need a plan. I’m going to definitely show you how to plan, you know me. But we need a plan that anticipates obstacles, challenges and failures and includes how you’ll deal with those and how you get back on track.

Create Your 2024 Roadmap, again, is only $87. And that includes the first planning session where I walk you through my goal-setting process, and the following coaching call where you can workshop with me, get your questions answered and also learn from your design peers. The link to sign up is desicreswell.com/roadmap-2024. And of course that will be in the show notes as well and I hope to see you there.

In the next episode, I’m going to be talking about a concept called thought errors and how this is impacting the results you’re able to create in your business. I’m really excited to talk about this topic with you. And until then, I’m wishing you a beautiful week. I’ll talk to you in the next episode.

Have you ever wished I could be your coach? If so, keep listening. For a limited time when you leave a rating and review for the podcast you’ll be entered to win a one on one coaching session with me. I can answer your questions and coach you on your unique challenges.

All you have to do is scroll down to the bottom of your podcast app, tap the five stars and leave a review. Tell me your favorite episode, why you look forward to listening every week, or why another designer needs to check out the show. It won’t take long, and as a thank you for leaving a rating and review you’ll have the opportunity to win a private coaching session with me.

Just click the link in the show notes to submit your review so I know how to get in touch. I can’t wait to select a winner and it might be you. I’ll talk to you next week.

Thanks for joining me for this week’s episode of The Interior Design Business CEO. If you want more tips, tools and strategies visit www.desicreswell.com. And if you’re ready to take what you’ve learned on the podcast to the next level, I would love for you to check out my signature group coaching program, Out of Overwhelm.

Enjoy the Show?

Don’t miss an episode, follow the podcast on Apple Podcasts, Spotify, or Google Podcasts.

Previous
Previous

66. Thought Errors

Next
Next

64. Big-Picture Planning for 2024