7. 3 Steps to Get What You Want – Step 2: Planning for Obstacles

Mar 22, 2023
The Success Minded Woman Podcast with Deidrea Kiesling | 3 Steps to Get What You Want – Step 2: Planning for Obstacles


We’re wrapping up step two of the three steps to get what you want today. I’ve talked all about planning for results and creating the plan to take you there, and now it’s time for the final piece of the puzzle: identifying obstacles and creating strategies and tactics to overcome the obstacles that stand between you and what you want.

I love this part of the planning process. When I was in corporate working on a project, identifying all the risks and coming up with a mitigation strategy for each one was always part of the plan. However, when it comes to our personal and entrepreneurial goals, missing this step is one of the most common reasons those goals go unachieved.

Life is always going to throw obstacles at us, so tune in this week to discover how these obstacles can make you better at what you do, and how following them will take you closer to your goal. I’m sharing how our thoughts and feelings make these obstacles seem more difficult to overcome than they need to be, and I’m giving you a simple strategy for dealing with any obstacle that gets in your way.


To celebrate the launch of the show, I’m giving away a $100 Amazon gift card to FIVE lucky listeners who follow, rate, and review the show. Click here to learn more about the contest and how to enter, I’ll be announcing the winners on episode 10!


What You'll Learn from this Episode:

  • Why we often neglect to identify obstacles when it comes to our personal and entrepreneurial goals.

  •  How obstacles have always shown us that we’re on the right path.

  •  One question to ask yourself when coming up with a strategy to overcome the obstacles that stand between you and what you want.

  •  How to address the emotions that make it harder for us to take action and easier for us to quit.

  •  Why it’s okay that sometimes you won’t know what you don’t know and the power of being naïve.

  •  How to come up with a simple step-by-step strategy for overcoming any obstacle.


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Full Episode Transcript: 




You’re listening to The Success Minded Woman episode seven. In today’s episode I will be sharing with you the number one reason why most people don’t achieve their goals, and how you can. The secret ingredient in goal-setting and achievement is to ask yourself this one powerful question: why have I not achieved this yet?

When you answer that question seriously for yourself, no excuses, no judgment, no justification, just be totally honest with yourself, the answer to that question will bring up all the obstacles that are in your way, and now you just need to solve for each one of them. Not knowing how, not having done it before is no evidence that you can’t do it now. So stay tuned where I will share with you exactly how to do this.

Hi, I’m Deidrea, wife, and mom to three teenagers, coffee snob, and certified life and business coach. If you’re a high-achieving, goal-oriented woman and you know you were meant for more, then you are a success minded woman and you’re in the right place. I’m here to help you make the money and the impact you’ve been dreaming of, to step into your confidence, create habits and systems to support you, ditch that imposter syndrome, and harness the power of your mind. If you’re ready to create a life and business you love, then let’s go. I’m so glad you’re here.

Hello there, welcome back. In today's episode we are going to be wrapping up step two of the three step process in how to get what you want. So step one was, decide what you want and why you want it. Step two is to make a plan. And over the last three episodes we talked about the components that go into your plan, your do goals versus your result and outcome goals, the power of 90 days at a time, the planning process that you're going to follow. And the program, the methodology, the philosophy, the coaching, the mentoring, whatever program you're going to follow to get your goal.

And this last piece of planning is what we’re going to talk about today and that is about identifying your obstacles and creating strategies and tactics to overcome those obstacles along your way. So I love this idea of thinking about obstacles and strategies as we work on our personal and entrepreneurial goals. So when I was in corporate consulting and project management this is actually a standard part of any project that we would do. We would always have as part of our planning process doing a risk mitigation. And basically that is identifying all the risks that we could anticipate that would possibly happen in the course of a project.

And then we would create a mitigation strategy against every possible risk. And that was part of the project plan. So we often miss this step when we are going after our personal and entrepreneurial goals. And it's one of the biggest reasons why most people don't achieve their goals. They don't anticipate and plan for all the obstacles, but the obstacles are the way.

That's what Ryan Holiday says in his book called The Obstacle is the Way. He writes about Marcus Aurelius, the emperor of Rome 2,000 years ago, who was at the time the most powerful man in the world. And he wrote that the impediment to action advances action, what stands in the way becomes the way. And I love that idea that the obstacle is the way and it was the way 2,000 years ago and it is the way now. There is no way to go except to go through the obstacles that present themselves along the way. We have to have obstacles. We need obstacles to learn and grow.

And I love how Brooke Castillo describes it. She says, “Every obstacle is a rung on the ladder to your goal. “Overcome an obstacle and that’s one rung, another obstacle, another rung. And you keep going and then you’re at the top of the ladder and that’s how you get your goals. And then you get to the top of the ladder and then you move your ladder and go up another hill. That’s just the way it goes. We’re earning and we’re growing, we’re setting big goals. We’re overcoming obstacles and we just keep going.

So you get your goal, and you have the strategic byproduct of all the lessons and the skills and the learning that you had along the way of stepping on all those rungs of the ladder and then you go after your next goal. So life is always going to be throwing difficulties at us and you can get better or worse because of those, it’s your call. So I know if you’re listening to this podcast that you are going to use your obstacles to learn and grow. And so we want to have obstacles because they show us the way.

So when you’re making your 90 day action plan for your goal you want to go through this process of identifying all the obstacles so that you can create strategies for them. So you’ll want to make a list of everything that's in your way, every excuse, every reason, every idea of why you can’t achieve it or what might get in your way. You can ask yourself this question, if it was possible for me to overcome this obstacle how would I do it? If it was possible for me to do this, what are all the things that I would have to learn and grow and skills that I would have to learn? What are all the things that are in my way?

And be open to the solutions and write it all down. So there are six main categories of obstacles that you will find when you go through this process. So I’m going to go through all six of them. So the first one and this is really the biggest one are all your thoughts and feelings. I know, you’re going to hear me say this a lot in this podcast and you probably have already that most everything comes down to our thoughts and feelings because that is what creates our actions or inactions in our life and that's where our results come from. So it always comes back to what we’re thinking and feeling.

So in this area of our obstacles of our thoughts and feelings, the common thoughts that most of us have when we’re going after a goal are things like, I don’t know how. I don’t know what to do. What if I make a mistake? What if people laugh at me? What if I can’t do it? I don't have enough time, enough money, enough energy, enough information. I don't follow through on things. I'm a procrastinator. I don’t know where to start. This won’t work for me. You don’t understand how busy my life is. I need more training. Who am I to think I can do this? I’ve tried this so many times before and maybe I just can't do it.

And you could probably go on and on, I know I could. And all of these thoughts, these disempowering thoughts create the feelings of doubt, fear, uncertainty, confusion, disappointment, regret, resentment, overwhelm. And all of those negative emotions makes it hard for us to take action and makes it easier for us to quit. So I want to tell you that all of these thoughts and all of these feelings, we don't have to make them go away. What we need is strategies to overcome them when the thoughts and the feelings come up.

So we’re not going to wait until all of these things are solved for, where we know exactly what to do and we’re 100% confident that we can achieve it and we have no doubts and we’re certain that we’re going to get there. No, we’re not going to wait till all of that because if we wait that long we’ll never get there. So what we want to do is create strategies for these obstacles of negative thoughts and negative feelings. And that's where managing your mind and that’s where mindset comes in.

So all of your self-doubt and all of these negative emotions don't mean anything about your ability to achieve your goals and your dreams, it is part of the process. Overcoming your obstacles is the way and feeling your negative emotions, allowing the discomfort of those negative feelings, that is the strategy and the skill that you will need to develop. So for all of these obstacles of negative thoughts and feelings all you need is a strategy to understand your mindset, to know that this is okay, that I'm going to allow these negative thoughts.

I’m going to allow these negative emotions and I'm not going to make it mean anything about me or getting my goal. And the skill that you want to develop is the ability to manage your mind, to manage your thoughts, to manage your feelings, to think on purpose and redirect your thoughts from those negative disempowering thoughts like I don’t know what to do to something like I’m figuring it out.

So for every negative thought that you have, for all of those thought obstacles, each one of those you want to come up with a strategy which is a thought you can think on purpose that will help you feel in a way that will help you take action towards your goals. So I literally want you to make a list of all of those thoughts and create new thoughts that you can think on purpose. And that is the skill to overcome negative thinking is to redirect your mind to better thoughts, that's it. That's a skill. It’s a lifelong skill and it's a lifelong practice. Okay, so that was the first category of obstacles.

The second category is the things that you know but you're not doing. So here is where you want to identify all of the reasons why you're not doing what you know you need to do. So you already know what to do but you're not doing it. So this is going to be a lot of your habits, your routines, maybe your lack of systems, maybe your identity about being a procrastinator or just whatever those things are you need to get those out of your head and onto a piece paper about what you think is blocking you from doing what you know you should be doing. So that's second category is the things you know but you're not doing.

Okay, the third category is the things you know that you don't know. So these are the things you know that you don't know, and you know you can find out. So an example is let's say that you have a goal you want to play the guitar and you don’t know how to play the guitar, you never played the guitar before. So the obstacle is you don't know how to play the guitar. And then the strategy would be to learn how to play the guitar. And then there is a lot of different ways that you can learn how to play the guitar. You could watch YouTube videos. You could get a guitar teacher. You could ask a friend to teach you.

You could go to some kind of event where other people are playing the guitar. There are so many ways that you could learn how to play the guitar. And so that’s something that you just decide. You pick a strategy, and you make a plan and you follow the plan. So anything that you don't know, you find out how you can get the information, the training, the program, the YouTube, the book, whatever it is. You know that there’s something you don't know and you go out and find the information. Okay, that’s number three, the things you know that you don't know.

Number four, now, this is the big one. This is a big I would say dream stealer and dream squasher and it's okay, we all have it and it's this. The things you don’t know that you don't know. So these are the things that you don’t even know that you don't know them. So, Ray Dalio, who is the successful hedge fund manager, he said this quote something like, “The more you know the more you know that you don't know much.” So this one will be an obstacle for you, and you can anticipate it by knowing it will happen and then when it does you can say, “Yeah, I knew there was going to be stuff that I didn’t even know I needed to know.” And that's okay.

So I love this example from Sarah Blakely who's the founder of Spanx. And she said, she was in an interview. I don't remember who was interviewing her, but she was asked a question about how it was when she got started and what she was thinking. And she went through a lot of trials and stops and starts along the way in building her business and getting started. And she said that she had no idea all the things that she didn't know about starting a business, about growing a business. And she said if she had known she probably would not have the courage to do it.

So it's okay that there is going to be things that you don’t even know that they're going to come yet, it's okay. There is a power in being naïve, it can actually be a strength. And there is actually a book called The Power of Naiveté: Embracing the Unknown. And one of the book reviews said about that book, as a woman grows older, fear and doubt set in due to fear. Shawn’s growth and belief in Naiveté expels the fear and doubt and gives renewed strength to being naive enough to look at tomorrow as the day to take action and say, “I will.”

And I love this concept, the audacity to dream big and have those big impossible goals comes from this power of naiveté, so it's okay that you don't know. It's okay that you don't know what you don't know to start. Just start and keep going and keep identifying your obstacles and creating strategies and you just keep going and you just keep going.

Okay, so the fifth area of obstacles are what tools or skills do you need that you don’t have? And this is a big category but basically for your goal you just need to do a thought download of all the things that you will need. So if you’re a new entrepreneur you may need to learn how to do bookkeeping. You may need to get some business software. You may need to open a business account or create your LLC or your corporation. Just all the things, all the tools, all the skills that you will need to go after your goals.

So just make a full list of those and then the strategy will be how you're going to do it and then you break it out into the steps, and you put it on your plan.

And then number six, this last category of obstacles are looking at your past for evidence of why this won’t work for you. So that looks like saying, “I've tried this and failed so many times. I've never done it before.” So whatever excuses that I know feel true and real that are coming from your past, either things that you didn't do or things that you did do, it really doesn't matter. Only bring from your past what will help you in your future, the rest of it, just leave it in the past because it's over. This is a big one, don't beat yourself up from things you did or didn't do in the past as evidence that you can't achieve your goal.

Okay, so I know that was a lot of obstacles and it’s kind of exhausting just saying all of this but it's okay. Slowing down now to make this list of all these obstacles will help you to speed up when you’re taking action because you already have anticipated and planned for all these obstacles. This is the way you’re being intentional and deliberate rather than if you didn’t plan for all these you would just be reacting a lot as these things came up along the way. So just get everything out, make a list until you literally can’t think of anything else that’s in your way.

When I did this one, I started my coaching business, I had over four pages of obstacles and strategies. And four years later I'm still in it. I'm still taking actions on those strategies that I identified four or five years ago. So it's an ongoing process but the thing is that the more you do this now it will get easier when you’re actually in it, when you're taking action and you’re in that messy middle and it’s uncomfortable and you’re not getting the results and you're trying and you're failing.

Having these identified obstacles and strategies will remind you that you knew this was coming, you planned for it and you’re going to keep going. So this all will help you in developing the confidence and strength to keep going. Now, I still notice all of my obstacles, all of the negative thoughts and all the reasons why I couldn’t overcome the obstacles, but I just keep going and this is what I want for you. This is why mindset is so important, changing your mindset and your negative self-talk from an obstacle into a strategy is one of the most important skills that you can have.

Instead of saying, “This is taking too long. I don't think I can do it. I don't think I have what it takes,” you can move your attention and redirect your thoughts and redirect your self-talk to I’m figuring out, this is happening, I know I can do it. And this is why mindset is so important, changing your mindset, changing your negative self-talk from an obstacle into a strategy is one of the most important skills that you can have. Doing a thought interrupt when you notice yourself thinking a thought, a disempowering thought. I don't know what I'm doing, I don't have enough information, I don't think I can do this.

Changing that to, I'm figuring this out, this is happening, it's on its way, I'm doing the best I can, everything is always working out for me. So when you catch yourself in a negative thought loop, in a negative self-talk cycle just interrupt that and say “Stop it. We are not going to go down that road anymore. We're doing this now.” And just redirect to those thoughts that you've identified, those strategies that you identified of your go to thoughts that you’re going to think on purpose.

And keep doing that, keep redirecting your thought every time those negative thoughts come up. And writing all of these obstacles out on paper or digitally if that's what you want to do, but get them out of your head, get them out of your brain and put them on a piece of paper. And now they’re a thing. They’re out in the world, they’re out of your head and that’s something that you can look at and you can actually refer to your obstacles and strategies document. I actually have mine printed out and I look at it as part of my planning process and my success plan.

I have a list of all of my obstacles, strategies and as part of my 90 day plans. So you can do this too. You can get it all out of your head and onto a piece of paper and start implementing these strategies. So you can find the obstacles by asking yourself questions like, what’s in my way? What are the obstacles that are in my way of achieving this goal? Why haven't I achieved this goal yet? Write down everything that comes up in your mind when you ask yourself these questions.

So Diana Nyad is one of my heroes and I love her story of believing in yourself and having the obstacles as the way. So she was the first person to swim from Cuba to Florida. She did this when she was 64 years old. She did her first attempt when she was 28. She tried and failed four times before she successfully finished, almost 30 years after her first attempt. So just think about that. For 30 years she had this dream, and she didn't give up on her dream. And I love this story of perseverance and determination to achieve a dream.

And her mantra and I love this and I have really embodied this myself is, find a way. It was impossible for her to do that. No one had ever done it before but she kept telling herself, find a way, and she did. And she did not give up and she found a way. And that’s what I want for you and me and all of us, to find the way. And how you find the way is through the obstacles, it’s so simple and yet so powerful. When you know that you will find a way there’s no room for doubt, if it will be achieved or if it's impossible. It confirms that there is a way, and we just need to find it.

So for her, she just kept saying this mantra over and over, find a way, and she just wouldn't give up on her dream and that she did it. And I love her whole story. You can find out more about her on YouTube. There’s a TED Talk that she did and she talks about this find a way and the whole story. So I love that talk but actually there is a documentary about her and the actual filming of this last successful attempt. It's an amazing documentary and I highly recommend that you watch it. I think you can watch it on YouTube. I really don't know where it is available right now, but it is very powerful.

I mean it's just so encouraging to see someone going after their dreams. When she came on shore after that swim, and I think it was almost three days. So I don't remember the number of hours. I think it might have been 64 hours of swimming, something like that. But anyways when she came on shore in Key West to finish her swim she could barely walk. She could barely talk. And there was interviewers there and asking her, her thoughts about it. And this is also on YouTube, the video of her actually saying this after the swim, it’s so powerful.

She can barely talk, her face is all swollen and she looks up and she says, “There’s three things I want to tell you.” It’s going to make me cry. You have to go watch this YouTube video. She says, “Never ever give up.” And then she says, “You can chase your dreams at any age, you're never too old.” And she said, “You need a team.” And then I think she fell down, she was so tired. It’s just so powerful and so inspiring to see women going after their goals, going after their dreams, believing in themself, knowing there is a way, finding the way and believing that and really embodying that. The obstacle is the way.

So I hope that I have convinced you that this is an important part of the planning process, to take time to identify the obstacles, create strategies and then turn those strategies into action steps that you're going to put on your 90 day plan. So you’re going to want to figure out all the steps for each of the strategies and then put them in the order, the time order that you need to do them and then put them on your plan. So you're going to put them on, figure out the order that you need to do these things and then put them on your plan, your monthly plan, your weekly plan. Some of these will need to go onto your daily plan.

So this is why planning is so important. You're going to get all of these details worked out before you even start. You're really going to set yourself up for success by going through this exercise. So I have another quote for you because you all, you know I love a quote.

So this quote is a quote about commitment and decision and it's by William H. Murray. And I can't remember the name of the book but I think it was about going on an expedition and he says, “Until one is committed there is hesitancy, the chance to draw back, always ineffectiveness. Concerning all acts of initiative and creation, there is one elementary truth, the ignorance of which kills countless ideas and splendid plans, that the moment that one commits oneself, then providence moves too.” All sorts of things occur to help one that would never otherwise have occurred.

A whole stream of events issues from the decision raising in one's favor all manner of unforeseen incidents, and meetings and material assistance, which no man would have dreamed would have come his way.” And that’s what Diana means by find a way, commit 100% and there will be a way and you will find it.

My intention with this podcast today is to show you there is nothing wrong with you. It doesn't mean anything about you that you haven't gotten your goal yet. Whatever obstacles you have had along the way it's all okay because you will learn from them and you will know they’re coming and you will make strategies and put the action steps on your plan. Your self-doubt and all of the negative emotions don't mean anything about your ability to achieve your goals and dreams, it is part of the process. The obstacle is the way.

And you have to do all of this. If you don't do this it won't work. Identify the obstacle, create a strategy, turn it into action steps and put it on your 90 plan. So I hope that you all will take this action step for today, get out a piece of paper or do it on your computer and make a list of all the obstacles that might get in your way from achieving your goal. Every thought, every doubt, everything that you are confused about, what skills you need to learn, what you don't know, what tools you need, everything that you think might get in your way of achieving your goal, write it down.

And then create a strategy, could be a new thought to think, could be an old thought to give up, it could be a class or a training or a group or accountability partner or new workout clothes or to tell your spouse or partner that you're going after this goal. Whatever it is, make a strategy for every obstacle that comes up and then write the action steps for that in your 90 action plan. And then next week we’re going to start taking massive action so get ready, we are going to get started.

So thanks so much for listening. I'm so glad that you are here, and we are on this journey together. I am so excited, I’m starting to hear from some of you all that are listening to the podcast and how you’re taking action on your dreams and goals and you're making big plans. And just keep all the questions coming and in a few episodes I'm going to be answering some of the questions that have been coming in. So feel free to send me your questions and I will answer those in, I think in two or three episodes from now.

So anyways thank you so much for listening, it means so much to me that you're here and that you’re going after your dreams and goals with me. So thank you so much and I’ll talk to you all next week. Bye.

To celebrate the launch of the show, I’m going to be giving away five $100 Amazon gift cards. That’s right, five lucky listeners who follow, rate, and review the show. It doesn’t have to be a five star review, but I do hope you love the show. I want your honest feedback so I can create the best show possible that provides tons of value. Visit thedreamacademy.com/podcastlaunch to learn more about the contest and how to enter. I’ll be announcing the winners on the show in episode 10.

Thanks for joining me this week on The Success Minded Woman podcast. If you like what you heard on the podcast and you want to know more, then head on over to thedreamacademy.com where you can sign up for my weekly success and mindset tips to help you create your dream come true life. Talk to you all next week, bye.


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