Plan to Succeed, but Prepare to Fail.

Planning improves your odds of success, but accepting risk, making decisions with incomplete information, and learning quickly from failure are what ultimately move a business forward.

Planning is essential to building a successful small business, but it doesn’t eliminate risk or guarantee success. In this episode, Henry Lopez explains why business owners must plan to succeed while also being prepared to fail, and how accepting uncertainty is a prerequisite for growth.

Henry breaks down the role of planning in both startups and existing businesses, explaining how business plans, financial projections, and annual strategic plans help reduce – but never remove – risk. He also explores the emotional side of failure, including fear, embarrassment, and decision paralysis, and why waiting for certainty often leads to stagnation.

Drawing from personal experience and past episodes, Henry outlines a practical framework for balancing disciplined planning with courageous action:

1. Plan deliberately
2. Assess the downside
3. Decide and commit
4. Review and adjust

The goal is not to avoid mistakes entirely, but to build a business resilient enough to survive them.

“The goal isn’t to avoid failure, it’s to build a business strong enough to survive the mistakes.”

If you’re stuck overanalyzing, afraid of making the wrong move, or hesitating to launch or grow your business, this episode will help you reframe risk, overcome fear, and move forward with confidence.

Plan to Succeed, but Prepare to Fail – FAQ:

Question: Why isn’t planning alone enough to guarantee business success?
Answer: Planning improves clarity and reduces risk, but it cannot eliminate uncertainty. Every meaningful business decision involves incomplete information and the possibility of failure.

Question: What does it mean to “plan to succeed but prepare to fail”?
Answer: It means creating a thoughtful plan while also understanding and accepting the downside risk, so you can act decisively and adjust quickly if things don’t work as expected.

Question: How should small business owners evaluate risk before making decisions?
Answer: Owners should assess the worst-case scenario, determine whether the downside is tolerable, and avoid risks that could cause irreversible damage to their finances or personal life.

Question: What causes decision paralysis in business owners?
Answer: Fear of making the wrong decision, embarrassment over potential failure, and the false belief that certainty is required before acting often lead to stalled progress.

Question: How can entrepreneurs overcome fear of failure?
Answer: By reframing failure as feedback, planning to limit downside exposure, and recognizing that progress requires decisions – even imperfect ones.

Henry Lopez (00:12):

Welcome to The How of Business Podcast. This is Henry Lopez. Planning is essential to business success, but even the best plans come with risk and no guarantees. And so on this episode, I’m going to share my thoughts on why you must plan to succeed, but also be prepared to fail and how accepting uncertainty, making informed decisions and learning quickly from the things that don’t work, how that’s often what separates us from getting stalled in business, whether it’s starting or growing a business, and achieving success and profitability with our small business. You can find all of the How of Business Resources, including the show notes page for this episode, and learn about my one-on-one and group coaching programs at thehowabbusiness.com. I also invite you to please join the How A Business Community on Patreon and subscribe wherever you might be listening so you don’t miss any new episodes.

Henry Lopez (01:02):

So let me share my thoughts and experiences on why planning matters, but why accepting risk and failure, and of course, correction, ability to make corrections matters just as much. If planning guaranteed success in business, then entrepreneurship would be easy, but it doesn’t. All of the planning in the world, all of the analysis, all of the learning, it doesn’t guarantee success. I do believe very much in planning to succeed, but you have to accept also that failure is very possible in any way, whether it’s complete failure, a catastrophic failure of the business venture, or failure is in something you might try or a new product line or something that you’ve changed in your business. This conversation is not about anti-planning. That’s certainly a key takeaway here. If you’ve been listening to my podcast for anytime, you know that I’m big on planning, especially if you’re starting your business and developing your business plan, or for existing businesses, creating a strategic business plan every year and then quarterly execution and planning.

Henry Lopez (02:01):

And this isn’t about fear. I’m not trying to scare you into thinking that all businesses fail, but this is a realistic grounded approach to building and growing a business or starting a new business if that’s where you’re at. So I want to chat with you about planning to succeed, preparing to fail and assessing that risk. What would that mean if your venture fails or your decision fails and how to consider or weigh both at the same time as you make decisions either to start or grow your business? So let’s talk about planning first, planning to succeed. Planning doesn’t eliminate risk, obviously, but it gives you a fighting chance. It helps you at a minimum, hopefully avoid some of the more obvious mistakes, especially as it has to do with your overall business model or maybe a very specific thing that if you planned or got guidance and input on, you might avoid and you can then not get hung up by that particular mistake or by going down a certain path that others have tried before and you can now see with some planning that probably doesn’t make sense for you either.

Henry Lopez (03:03):

It’s not about hope. It’s not about hoping something will happen, hoping that we will be successful. It’s about developing a strategy. So planning is about strategy, not so much about hope. And it’s about intentional direction, having a blueprint, a path, a guide, again, either to starting your business or to growing your existing business. It’s not just about staying busy, which is often what we hide behind. I don’t have enough time to plan because I’m busy or I’m just getting things done. And all of those are legitimate concerns, but I’m here to assure you that planning will pay off either in starting or growing a small business. So planning forces clarity, it forces alignment, it exposes assumptions because ideally you’re having this plan validated to some extent or challenged is probably a better word by someone else, a coach, a mentor, a peer, someone who’s done it before.

Henry Lopez (03:53):

And planning helps you create decision filters, go, no, go gates. I’m going to do some analysis, some planning perhaps. And then decide, go, no, go, does this decision make sense? Do we move forward? If you’re starting a business, let’s talk about it from that perspective again for a moment. Then I think you must have a business plan. There’s episodes that I’ve released on this in specific episode 382 on small business plan. So listen to that episode. If you’re in that stage where you’re planning for the start of a business and you don’t have a business plan, that’s a great episode to go and listen to. Episode 382. My big emphasis is you’ve got to have some type of a plan. And one of the key components of that plan is your financial projections. You have to at least model and project a P&L to validate the financial side of this business model that you’re about to launch.

Henry Lopez (04:39):

And the way that I like to measure whether a business model is healthy, whether it’s a good business model, which leads to then, is this a good business idea is certainly in the startup phase, you’re trying to project and validate through those projections that you can be profitable in this business venture and then it can scale beyond you. If that’s what you’re looking to do. If you’re just looking to be a solopreneur, then that might be slightly different, but even in those cases, you need to plan. So for starting a business, you have to have a business plan and financial projections. The value is not in the document. In other words, you’re not writing a novel. And often that’s where people get hung up is in the formatting or the grammar. Often this plan might be just for you. Now you may have to have a version of it for your bank if you’re getting a loan or perhaps an investor or someone else you’re bringing into the business.

Henry Lopez (05:25):

But its first and foremost purpose is to help you put to paper and think through and validate the business model that you’re proposing. And projections aren’t just prediction. You’re using them to stress test, to validate and determine when will I break even? When will I get a return on my investment? And within what timeframes are those? And does that make sense to you for what this business needs to do for you and your lifestyle?

Henry Lopez (05:55):

This is Henry Lopez, briefly pausing this episode to invite you to schedule a free coaching consultation with me. I welcome the opportunity to chat with you about your business plans and offer the guidance and accountability that we all need to achieve success. As an experienced small business owner myself, I understand the challenges you’re experiencing and often it’s about helping you ask the right questions to help you make progress towards achieving your goals. Whether it’s getting started with your first business or growing and maybe exiting your existing small business, I can help you get there. To find out more about my business coaching services and to schedule your free coaching consultation, please visit thehowabbusiness.com. Take that next step today towards finally realizing your business ownership dreams. I look forward to speaking with you soon.

Henry Lopez (06:49):

Now let’s look at it from the lens of an existing business owner. So perhaps you’ve been in business for a year or two and you’re past that startup phase, but you still feel stuck. The growth isn’t there. The profitability isn’t there, at least not consistently. Well, that’s where planning comes into play as well. I think at the beginning of every year, or if you haven’t done it, then do it now, is you need a strategic plan. Now, that strategic plan will include a longer term vision. Where do you want to go? And that horizon, I think for small businesses, typically is in the two to five year range, let’s say five years. And then specifically this year, what are our goals? What are our objectives? What’s our focus? If we need to pivot, what is that? What does that look like? It gives us focus for this year in alignment with where we want to go longer term.

Henry Lopez (07:32):

And it could be as simple as you want to get the business to consistent profitability. Well, how will you execute on that? And this most critically is you got to break down that annual strategic plan into quarters so that you can get something done. A quarter is typically long enough to get something done that’s meaningful, but not so long that you can’t then, as you get to the end of the quarter, assess what’s worked, what’s not, what’s going on overall, and then adjust course if you need to. Episode 590, I would recommend if you need help with how to put together an annual strategic plan. So listen to episode 590 on annual strategic planning, if that’s where you’re at in your business. A plan, again for an existing business, an annual plan will help you align your priorities both forwards and to today. In other words, where are we going?

Henry Lopez (08:17):

Is this plan in alignment? Does it help me get there? Does it move me along that path? And as I’m executing on a quarterly, weekly, and daily basis, are those things, as I prioritize my activities, the most important things that I work on, are they in alignment with helping me make progress on my quarterly plan, tied to my annual plan in alignment with where I want to go longer term? Because we all have limited resources, obviously, as small business owners, both our time, our team, if we have a team, our money, of course. So this is about helping us make the right decisions as to where we allocate those limited resources. All right, so that’s something for you to think about there from a planning perspective. You’ve got to have a plan to succeed, but the flip side of it is the reality of failure.

Henry Lopez (09:02):

And so that’s the second part of this, prepared to fail. Planning reduces risks, but it never removes it. And emotionally, you’ve got to get past that fear of failure is often what happens, especially when you’re first starting a business, that fear of failure. But if you’re in an existing business, often, again, maybe you’re approaching decision fatigue. Maybe you feel like you’ve tried everything and nothing’s working or you’re not sure what’s not working. So wherever you are, the planning helps with that, but there is this fear of failure that you have to overcome. And there’s the reality of failure because it’s not just a fear, it’s based in reality. That’s the cold, hard truth, is that businesses are not guaranteed. And you can read all kinds of different research depending on what segment you’re in as to the probability of failure. So the reality is that if you’re searching for maybe getting it in another course or more research or a more detailed business plan or approval from your friends and family, you’re not going to find a guarantee.

Henry Lopez (10:00):

There are no guarantees in business. And listen, I would love to find that. I often find myself in this paralysis. Certainly when I was starting some of my earlier businesses, I have a tendency to be overly analytical and at some point it’s diminishing returns. One of the things that’s helped me there is to have a partner who’s a different type, takes a different type of approach in how he assesses risk. Or getting a coach or a mentor that’ll say, “You’ve done enough research, you’re ready to move forward and take that leap of faith because if you continue waiting until you’ve got it perfect and guaranteed, you’ll keep waiting forever because there’s no such thing.” Every significant meaningful business move, whether it’s related to starting your business or an existing business owner that’s making decisions on a daily basis, it’s filled with uncertainty. You’re going to have to make decisions with incomplete information, and there’s always a risk, both real, financial, and emotional risk.

Henry Lopez (10:52):

I did an episode about a failure that I had, and this was one of the early episodes on the How a Business Episode 35, and we, myself and my business partner, David Begen, share the story of having to close our second frozen yogurt business that we owned. And we share there, I think pretty candidly, the pain of going through that. And we shared some of the reasons why we closed it and mostly the emotional side of what that was like to deal with as a business owner. Nobody likes to fail. And certainly entrepreneurs hate to fail. I hate to fail or lose, but I realize that that is part of this undertaking, that that is part of being a business owner, that it comes with the territory. And so what I do is I try to mitigate that risk. I try to calculate that risk and then I make a decision.

Henry Lopez (11:39):

I make an assessment. Is that a risk I’m willing to take? Is the business model that I am preparing to launch or that I have, does it have the probability for success, enough probability for success? And then I take a leap and I move forward knowing that I might have to quickly adjust. So this topic of the risk of entry, of the fee of getting into business or continuing to run a business, it’s relevant for starting a business. It’s relevant to pivoting a business model, maybe you might even be successful, but you’re looking at expanding or continuing to grow, adding offerings, adding headcount, adding locations. All of these things come with risk. Remember the key idea here is on risk. You don’t eliminate risk. You decide which risks you’re willing to carry. And part of that is determining what’s the impact going to be on you and your family.

Henry Lopez (12:29):

And then of course on your staff and your partners and other vendors or partners that are involved in the business. I want to recommend episode 292 titled, Are You Ready to Start Your Business? And that episode I cover, helping you determine whether you’re ready, willing, and able to start, or even to continue operating a business. Are you ready mentally and emotionally? Are you prepared for it? And this speaks directly to this overcoming of the fear of failure. And what I have found, just to go off on a tangent, a moment on that, it’s of course particularly important here and can be paralyzing when we’re looking to launch a business. It could also apply to making a decision to grow a business. I have found that the number one thing that keeps people from starting a business, other than they don’t have the financial resources or the time is the fear of the embarrassment of failure.

Henry Lopez (13:22):

In other words, telling your friends and family, remember that business that I was so excited about and I told you all about and you came to the grand opening, well, I had to shut it down. Boy, that’s a big blow to the ego and I’ve been there and it’s not easy. And if it happens again, which it may well for me in my business career, it won’t be any easier then. In fact, it’ll be worse because I’m supposed to know everything about business. The reality is that there’s a little bit of luck involved. And so that fear can be based on the emotions of it, or it can be also because really what I have on the line is significant. It’s monumental. So that’s the ready part. So ready, willing, enable. The willing part is, are you willing to make the sacrifices and the things that are going to have to change perhaps to achieve success and enable has to do with the resources.

Henry Lopez (14:09):

You actually have the resource both financially as well as time and health, your health to dedicate to starting and growing a business. So that’s the risk side of the equation. Plan to succeed, but be prepared to fail. And that is just a reality statement there. I know at first blush, it might’ve seemed like that’s very negative or that you’re telling me, Henry, that my business will fail. Now what I’m hoping you’re starting to take away from this, and maybe you’ve already thought through this, is that there are no guarantees in business. Planning helps us avoid some of the obvious stuff, but then the reality comes when we start. And so then we must be courageous enough and quick enough to identify and adjust our business model as soon as the market starts to tell us what it likes and what it doesn’t like. And making sure that the risk that we’ve taken is tolerable for us, not from an emotional perspective.

Henry Lopez (14:59):

What you do have to have in alignment is making sure that that risk isn’t going to ruin you. I often ask people as I’m coaching them that are starting businesses, “What’s the worst case scenario if this business fails?” And answering that question was very personal, obviously, but can answer or can tell you a lot about, “Am I taking too big of a risk?” If you’re an existing business owner and you’re about to make a big decision, same question applies. If you make the wrong decision on this, what happens? What’s the worst case scenario? And similarly, if the worst case scenario is highly impactful, highly negative, destructive, disruptive, then maybe you make a different decision. Maybe you make a smaller decision. Maybe you break that up into steps so that it’s not as impactful if you get it wrong. And I’m here to tell you that you’re going to get a lot of decisions wrong.

Henry Lopez (15:48):

This fear of making the wrong decision leads us to paralysis, and then everything gets stalled. I just rereleased an episode about overcoming decision paralysis, episode R423, and that’s a great episode to listen to if you’re feeling some of this as we all go through times where we reach decision fatigue and we hit paralysis, we hit a wall. So I encourage you to listen to episode R423 on this topic. Just to emphasize your growth of any kind, whether it’s personal or growth in launching and then growing a business, requires you to make decisions, hard decisions, decisions that come with risk. And risk includes the possibility of being wrong, of failing. But progress, especially if it’s aligned progress, planned progress, beats perfect because perfect never shows up. Now let’s balance these two things. A mature business owner or a person who’s ready to start a business will plan rigorously, but act courageously.

Henry Lopez (16:45):

So you have to have a balanced mindset here. You want to plan thoroughly before you act. You want to accept that there’s always going to be uncertainty when you do act, when you do make that decision or move forward, and then learn quickly for what happens after you do make that decision or act and adjust as you need to. So a practical framework is to plan deliberately. So that’s to strategize, that’s the numbers, those are the assumptions. You want to plan, you want to think a couple steps ahead. Then you want to assess the downside. What’s the exposure? What’s that worst case scenario? What’s the financial exposure? What’s the cost and time? Can I reverse this decision or am I stuck with it? What’s the worst case scenario if I get it wrong on this decision, if the business fails or this particular decision leads to some sort of failure?

Henry Lopez (17:33):

So one, plan deliberately. Two, assess the downside. Three, decide and commit. You have to take that leap of faith. You can’t continue to overanalyze. That’s what leads to paralysis. I’m not saying don’t take your time on big decisions. I’m saying at some point you got to make a decision. Otherwise, you will stall yourself in your business. You can’t go on endlessly hedging or putting it off and get help. Get help to help you with deciding, with assessing the risk. Maybe you get some help from your CPA to determine the risk of bringing on new people next year and what that’s going to do to your cost structure. Maybe you get a coach. This is what I do for my clients to help you with planning for growth. Or maybe you get a coach or a mentor to help you with launching your business, to help you validate that business plan and your financial projections.

Henry Lopez (18:15):

What you want to do though when you get help is get it from people who have done it before. Your friends and family, they love you and they want the best for you, but they don’t know how to challenge you or guide you through this. And so be careful that you get that help from people who have done it themselves or are doing it currently. So that’s three, deciding, commit, move forward. Four is to review and adjust. Learn fast, adapt without ego involved, right? Be willing to let go of things that you were so certain were going to work out. Even if you’re the inventor or the author of it, fail fast, adjust or pivot. So those are the four steps to a practical framework to help you with this and to balance planning and the reality of failure. So to wrap it up, what I want you to think about is that planning, while it doesn’t guarantee success, refusing to plan or thinking that planning has no value is going to guarantee that you struggle.

Henry Lopez (19:09):

That’s a guarantee. So we want to plan so that we have a blueprint, a path that’s in alignment for where you want to go. And then overcoming the fear and embarrassment of failure is often the key to success in business, just overcoming that. It’s not necessarily that successful entrepreneurs are risk takers. I really, when people tell me that I think I don’t consider myself a risk taker, that’s not really my personality. But instead what I’ve done and what other successful entrepreneurs do is assess and carefully calculate what the exposure is, what the risk is, and then realize that there’s a bit of risk involved in every decision like that. But at the other end of it, you can’t be so careless as to think that there are not mistakes you can easily avoid through some planning. Planning is also how we measure the risk appropriately so that we can determine if it makes sense to move forward, regardless of that inherent risk associated with any business, either because you’re launching or making decisions in your existing business.

Henry Lopez (20:08):

The goal isn’t to avoid failure, it’s to build a business strong enough to survive the mistakes. It’s another way, I think, to look at it. The key takeaway that I want you to consider from this episode is that successful business owners and entrepreneurs don’t rely on just hope and don’t rely on the certainty of their egos or the arrogance of their experience or previous successes even. They rely on thoughtful planning and a clear understanding of the risk that they’re taking by making this decision. And so when you combine discipline planning with the willingness to move forward and courage, then adjust to the realities and learn from the mistakes that you’re going to inevitably make along the way, then you give yourself the best chance to build a resilient business that can survive setbacks and grow over time and become profitable and scalable. This is Henry Lopez, and thanks for joining me on this episode of The How Web Business.

Henry Lopez (21:01):

I wish you the best as you start and grow your successful and profitable small business. I release new episodes every Monday morning, and you can find the show anywhere you listen to podcasts, including the Howe Business YouTube channel and at my website, thehowofbusiness.com. Thanks for listening.