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OK, this might seem weird, but one of the things that often leads to colossal business mistakes is unrelenting optimism.

I mean, if you're going to be an entrepreneur you pretty much need to be an optimist… you need to have the belief that you can create something out of nothing – because that's what we all do pretty much every day. And above all else, you need to protect your confidence (and you need to avoid poisoning your brain).

But you have to be careful… because that optimism can get you in trouble.

And this ESPECIALLY true when you get a bunch of entrepreneurs together… say in a mastermind group or a team meeting.

Lots of times, when you get a group like that together, there's some subtle pressure for everyone to be super positive… after all, you don't want the other people thinking you forgot to listen to your “positive thinking” audios, or that don't have a “can do” attitude, or that you're a buzz kill.

But all that optimism can be dangerous…

Here's why… there might not be such a thing as a bad idea when you're brainstorming… but when it comes to BUSINESS there are PLENTY of bad ideas.

Your plans have to be realistic. Your research has to be realistic. Your offer has to be realistic. Your prices have to be realistic. And you have to avoid obstacles, road blocks, and potential negative outcomes for your plan.

You don't win at business just by having a positive attitude. You need a strong, realistic plan… and you need strong execution.

(Dwight D. Eisenhower said: “Plans are useless; planning is everything.”)

One of the tools that I use in my planning is something called a “Strategy Circle”… I learned this technique from my business coach Dan Sullivan

Basically, you start off with an idea for a project and then the FIRST thing you do is brainstorm all the OBSTACLES for that project.

That might sound strange, but the cool thing about looking at obstacles first is it legitimizes looking at the negatives… so you avoid the “sticking your head in the sand” syndrome. You avoid blind optimism.

When you list all the obstacles, keep pushing until you have a BUNCH of potential obstacles – aim for ten or more of them.

The next step is to brainstorm STRATEGIES for dealing with EACH obstacle.

After that, move on to the RESULTS you will see from the project – basically at this point you're building up the “why” behind the project – why should you overcome those obstacles and complete this project.

This “Strategy Circle” approach is a great tool to use by yourself, and it's even better to use with your team. It sounds simple, but it's super-effective. Give it a try.

(Strategy Circle is a trademark of Strategic Coach.)

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76 Replies to “Let’s Go Negative”

  1. Hi Jeff,

    This is a fantastic post. Thanks for taking the time to share your philosophies. At the end of the day, an extremely optimistic idea is only the beginning to preparing action steps. However, to successfully implement action steps we must identify obstacles. Then, being realistic becomes identifiable and your outcome will be much more rewarding. The strategy circle is a powerful tool. Thanks again!

  2. Thanks Jeff this is awesome!

    I do mastermind groups and brainstorming often and look forward to using the “strategy circle” — absolutely brilliant!

  3. Hey Jeff,

    This post really rings true for me.. I was overly-positive because of The Secret and The Science of Success, and then I listened to my friends and started listening to a Tony Robbins program.

    They made me realize that I’m allowed to not be positive 100% of the time, and I can be disappointed and think of negative things and still be a good person.

    I appreciate this post, I think it’s a little bit of a wake-up call.


  4. Jeff:
    The approach that you are talking about Obstacles,Brainstorming,Opposition Arguments and Research does not remind me of a Dan Sullivan idea like you modestly suggest. Rather I seem to see that thread all the way through my various editions of the Product Launch Formula. Sort of my motto here” Believe in your own b.s. Act at your own peril.” The former ideas of the positive boys around the table reminds me of the circle jerk mentality. The latter of the true Mastermind where you can be fair game unless you have done your planning for the market.
    The latter usually wins.


  5. Great post, Jeff.

    I really like the tease out all the obstacle.

    I often recommend a similar approach, with a slight twist. It’s not just the obstacles that often become a problem – it’s the ASSUMPTIONS we make vs. the actual FACTS, too. Because each of us have an internal “map” of what we think is reality, it’s relatively easy to make mistakes by basing important decisions on what we believe to be true, which isn’t always the case.

    So we recommend clients develop a list of all of the things that must actually come true in order to succeed, then assign a score to each item between 1 and 5, and objectively review this list with a group (ideally). Higher number represent increased certainty that the stated assumption is actually true.

    5 == FACT
    3 == Reasonable Assumption, Needs Validating
    1 == Pure Theory and Assumption, Needs a “Learning Plan”.

    For all items scored 3 or less, a “Learning Plan” is needed to turn this assumption into fact (or uncover that it is not actually true and then come up with a mitigation plan for addressing it).

    I’m intrigued with how one might use both methods to further reduce risk. Every new project is always a “learning journey”. I guess that’s a key reason we like be entrepreneurs – it’s adventurous! (but it’s always more fun to be right and win)

    Thanks again for sharing this!

  6. It really is a wonderful paradox. Your advice to move head-on into the negatives gives me a very positive (empowered) feeling. Thank you once again for your beyond-the-obvious wisdom and great guidance.

  7. Great post with an important message. Optimism is great, but balance is essential. Often that will include exploring the “what if” scenarios.

  8. Thirty five years of running businesses has taught me to pay plenty of attention to the potential downside. Anyone can get high and giddy on the potential of a great new idea. At times I’ve almost gotten cynical about people who focus to much on how cool the project is, and too little on honestly looking at what could go wrong, and then creating workable strategies do deal with the potential worst case scenario.

    Thinking what could go wrong and then encouraging people to come up with ways to deal with those things if they happened is surprisingly foreign to many business people.

    To me getting excited about great ideas is the easiest thing in the world. It’s right up there with being a professional critic. All you have to do is engage your mind in the world of fantasy and let it rip. I’ve sat in meetings where people were already talking about how they were going to spend all the money they were going to make — on an idea that had yet to make a dollar. [I’ve learned a long time ago to run from that degree of naivety]

    I’ve also noticed that even when you take the time to identify potential threats (SWOT analysis anyone?) and you decide the project is a go — it is rare that you don’t encounter obstacles or threats nobody expected. But I’ve always been very grateful when someone on the team had taken steps to ensure there was adequate coverage for the unexpected and it turned to be just the thing most needed. Those kind of people are rare and the most valuable there are in business.

    It’s also rare that a project goes more smoothly and more easily than anyone anticipated — but when that happens it normally happens when seasoned veterans planned for unexpected eventualities, had conservative expectations, employed reliable people for execution of critical elements, and had relentless persistence.

    Thanks for a great article! With a dramatic acceleration of regulatory obstacles in recent years coupled with accelerated unreliability in many sectors — I think we need to appropriately increase the attention we put on vetting our business ideas.

  9. Jay Rosenberg


    Hi, Jeff,
    You are preaching to the choir! Yes, yes, we all fight the battle every day.
    Mid-launch right now and, as alway, getting high on the challenge of delivering great launch to the customer. It sharpens the senses and exhausts the body! Others coming up fast.
    I signed in for Dan Sullivan’s report and read the first paragraphs which are, to me, the test of good thinking by the writer. Can’t wait to dig in.
    Meanwhile I am building out TQM, The Quant Method, personality based marketing which is turning out to be a powerful enhancement to PLF.
    All the best to you, as always. Jay

  10. I could not agree with this more. We must use what we learn from the law of attraction. We also must focus on ideas and goals that are achievable. Remember the SMART Goal setting acronym. S- specific, M-measurable, A- achievable, R- realistic, T-timely.

    Very bold post, thank you.
    Rob Triggs

  11. There is a section in the book “Good to Great” where the author conducts an interview with Admiral Stockwell, hero who endured 5 year stretch in the Hanoi Hilton POW camp. After a robust story of super human endurance he answered the question “…what about the guys who didn’t make it”? His reply: “That’s easy, they were the optimists…the guys that kept saying we’ll be out by Christmas…we’ll be out by Easter etc.” His strategy: Unwavering conviction that you will prevail in the end, with an unrelenting willingness to face the brutal facts”

  12. Agreed. Some of my most productive masterminds are also the most uncomfortable because we pick ideas and strategies apart. Eben Pagan has it right – short term pessimism – long term optimism. Thanks for the new approach.


  13. Steve Looser


    Thank you Jeff for the wise and actionable advice. . I know that one of my biggest failings in life has been overconfidence and diving in head first without first testing the water.

  14. I feel a lot of pressure to be “relentlessly optimistic” even in the face of what, clearly, has the potential for being an ongoing train wreck. Unfortunately, the bearer of the bad news…

    My whole take on it is if people want my _real_ opinion, they’re gonna have to pay me a lot of money.

  15. I will put this into action tomorrow!

    Thanks Jeff, I have learned something today.

  16. I really like this article and the simple way it sums up the steps to developing a business idea while paying attention to potential problems you mignt face. I believe this is a more realistic way to approacing business.

  17. Hi Jeff,

    I’ve been lurking here for a while and I just wanted to say that this post really spook to me. It’s always important to consider the obstacles when starting a new project. It’s easier to deal with them if you have strategies in place.


  18. Excellent approach in my opinion, even though some people will call it a negative approach, or label me a depressive (actually I am one) so am not offended by it. Some research shows that mild to moderate depressives might easily warm to this approach, because it is more realistic than the rah-rah positive meetings, and depressives tend to relate better to reality.

    Secondly, listing obstacles gives leaders the chance to address the ever cumbersome ego and ego issues that often arise amongst the team members, how they could be recognized as issues and how they might be most effectively “handled” and overcome for the best resolution of the project and most enlightening learning experience for one, some or all team members. “Best possible project results” are too often waylaid by the ever-so-powerful ego which tricks people into thinking they are making progress when they really aren’t.

    Thanks to commenters for the useful additions to a powerful strategy.

  19. Totally agree Jeff. As business owners & entrepreneurs, we need optimism and passion, but we also need to keep our eyes and minds open. Blind optimism and blind passion are two ingredients for business disaster – sooner or later. It’s not about being cautious and making sure everything is right before you start – otherwise most people would never start.

    Your approach of forcing the listing of many obstacles and then planning strategies to deal with each obstacle BEFORE looking at the results from the project is very useful in that many people look at the positives of a business or project first and then skip over the ‘negatives’, not wanting to acknowledge them.

    Your approach reminds me a lot of Edward De Bono’s Six Thinking Hats. Here’s some info on it…

    How to Use the Six Thinking Hats
    To use Six Thinking Hats to improve the quality of your decision-making, look at the decision “wearing” each of the thinking hats in turn. Each “Thinking Hat” is a different style of thinking. These are explained below:

    White Hat
    With this thinking hat, you focus on the data available. Look at the information you have, and see what you can learn from it. Look for gaps in your knowledge, and either try to fill them or take account of them.

    This is where you analyse past trends, and try to extrapolate from historical data.
    • What facts would help me further in making a decision?
    • How can I get those facts?

    Red Hat
    Wearing the red hat, you look at the decision using intuition, gut reaction, and emotion. Also try to think how other people will react emotionally, and try to understand the intuitive responses of people who do not fully know your reasoning.
    • How do I really feel about this?
    • What is my gut feeling about this problem?

    Black Hat
    When using black hat thinking, look at things pessimistically, cautiously and defensively. Try to see why ideas and approaches might not work. This is important because it highlights the weak points in a plan or course of action. It allows you to eliminate them, alter your approach, or prepare contingency plans to counter problems that arise.

    Black Hat thinking helps to make your plans tougher and more resilient. It can also help you to spot fatal flaws and risks before you embark on a course of action. Black Hat thinking is one of the real benefits of this technique, as many successful people get so used to thinking positively that often they cannot see problems in advance, leaving them under-prepared for difficulties.
    • What are the possible downside risks and problems?
    • What is the worst-case scenario?

    Yellow Hat
    The yellow hat helps you to think positively. It is the optimistic viewpoint that helps you to see all the benefits of the decision and the value in it, and spot the opportunities that arise from it.

    • What are the advantages?
    • What benefits will this bring?
    • What would be the best possible outcome?

    Green Hat
    The Green Hat stands for creativity. This is where you can develop creative solutions to a problem. It is a freewheeling way of thinking, in which there is little criticism of ideas. A whole range of creativity tools can help you here.
    • What completely new, fresh, innovative approaches can I generate?
    • What creative ideas can I dream up to help me see the problem in a new way?

    Blue Hat
    The Blue Hat stands for process control. This is the hat worn by people chairing meetings. For example, when running into difficulties because ideas are running dry, they may direct activity into Green Hat thinking. When contingency plans are needed, they may ask for Black Hat thinking, and so on.
    • Review my thoughts.
    • Sum up what I’ve learned and think about what the next logical step is.

    Six Thinking Hats can be used individually or in a group situation. It’s a powerful tool and an invaluable process.

    Richard Keeves

  20. Great post Jeff… I know what you mean about being the buzz killer in the mastermind group. But, somebody always needs to look at the negatives to keep it real.

    Ian McConnell
    Western Australia

  21. I see now that “going negative” can refer to the process of filtering ideas through the obstacles that could occur. Outstanding information that I will put to use right away.

    What I disagree with is the idea that optimism is blind. In my view this is a misrepresentation and not optimism at all. The belief that things will eventually turn out for you does not exclude realism.

    Naive maybe, but not overly optimistic.

    Thanks again for the great info!

  22. This is a really insightful perspective Jeff.

    At one point in my life, I was a huge proponent of the adage; “Your Attitude determines your Altitude”. One day, a very successful businessman and author presented a similar challenge to my thinking. He asked; would you rather have have a team member with a ’10’ in attitude and a ‘3’ in skills or someone with great skills and a lousy attitude? My “programmed” entrepreneur response came quickly–give me the great attitude guy! A

    He nailed me with his perspective; “It’s easier to teach someone with a high level of skills how to have a great attitude–but you may never teach the guy with the great attitude, skills. Give me the guy with the skills every time”.

    My paradigm shifted that day and it changed again today after reading these thoughts. Thanks for the advice.

  23. Love it man! nobody talks about this Jeff…

    Optimism is key, but when you don’t look at the downsides of your business, offers, niche, etc that can lead to continuously spending money on a project that will never profit.

    Thanks for the post my man!

    Brian Fanale

  24. Jeff,

    That is one of the most sensible approaches to determining the viability of an entrepreneurial project I have heard yet.


  25. I always appreciate honesty! Thanks for the insight and strategy.

    There’s no such thing as failure, just failure to plan.

  26. Good points. I’m currently reading “American Mania” which is about how American’s are genetically engineered to be risk prone due to a dependency on dopamine – the brains reward juice. It’s always a good idea to have some built checks and balances in the mix of planning.

  27. Synergize Inc


    Or all you Optimists can just accept that
    1) you need at LEAST one Realist on EVERY team to keep you all out of big trouble,
    2) you need to actually LISTEN to your Realist(s) on each team to keep you all out of big trouble,
    3) you need to CONTEMPLATE the Realist’s comments as actual possibilities to keep you all out of big trouble instead of worrying about your optimistic “feelings” and inflated-egos getting detoured.
    4) you need to APPRECIATE and THANK the Realist(s) on the team for having the courage and integrity to not cave into peer-pressure so as to to keep you all out of big trouble. Their job is much harder than the Optimists, any day, every day.

    Or continue going about building teams of yes-clones with unidirectional vision with the capability of driving directly and unhesitatingly off the next business cliff. LESSON: You WANT differing opinions between your members. Without them it simply means that you are missing a LOT of what’s actually going on, like cliffs. Or maybe I’m wrong. It’s not like the entire world could ever go into a financial depression based upon numerous non-stop and deregulated bubbles that entire industries or even countries bought into so much that many are facing NATIONAL insolvency. That would be just crazy talk…

    Identifying problems and solving them immediately is the way to go and Realists are those that have the ability to do that best, not Optimists. Go take a couple of them out to eat some time in appreciation.

  28. Thanks Jeff – personally I used the old fashioned SWOT (Strengths, Weaknesses, Opportunities, Threats) planning approach for any reasonable size project. It may be an old method but it still works a treat. This always gives you a broader and more realistic picture of any planned project.

  29. Steven @ the real debt


    You’re right in my mastermind session if someone brings up a negative it can shift the mood of the meeting, but I’ve found that these are my most productive sessions.

  30. Hey, for all those “realists” optimism is not such a bad thing — nor the blinders they wear — Jeff is absolutely right, and the method works specifically by relying on the likelihood of bad ideas being aligned with a foucs for the “badness” of those ideas, the obstacles. I routinely use positive moods to build out options and negative ones to tear them down but never thought to do it the way he specified: in fact, now, if I were to do it again, I would probably set up (optimist/optimization nucleus center) a series of concentric circles, defining areas of inclusive and challenging growth barriers and figure a way to define growth linearly from the center radius across each circle/barrier using a quadrants method of linear curve (each +/-90 defining some 1 of 4 aspects and colored to index outcomes of any given approach across the barrier circles with each quadrant grouping the problems of a given barrier, say eg, capital being one barrier circle, growth another, and the problems written into the quadrants as points in between startup and rampup portions of successive circles). All this is an html musing though, it is impractical for pen and paper but would be a terrific software tool …

  31. Great post Jeff, and really thoughtful comments. There is such an ingrained “either/or” mentality that underlies much of our thinking. It is healthy to balance optimism with healthy concern for challenges and obstacles. I like the Strategic Coach’s strategy circle as well as being reminded about the 6 hats.

  32. Jeff,

    Who was it that said, it isn’t how you manage the project that guarantees success but how you deal with the unexpected.

    Looking at obstacles first has lots of merit.

    Thanks for sharing,


  33. I like Jeff’s approach to business concepts and found the threads to be right on. It’s a good idea to have one or more devil’s advocates in the brainstorming session(on team).

  34. boudewijn lutgerink


    My experience is that most people tend to interprete “positive thinking” as not to look at down sides of the matter at hand. many times I heard “you MUST think positive!” (what is so positive about forcing yourself?)
    Sticking the head in the sand (called “ostrich policy” in the Netherlands) is no good and not positive.
    I like this approach of looking at the downsides of any matter first. Kind of reality check.

  35. Optimism is great and all, but having a grounded, balanced view keeps us from running into those brick walls that our blind optimism failed to allow us to see.

    Eliyahu Goldratt’s entire “Theory of Constraints” is based on recognizing and removing obstacles. They have to first be embraced and understood before a strategy and effort can be formulated to remove them.

  36. Great post Jeff! This knowledge will come in handy in the near future. I have been a constant victim of TOO much optimism and I agree it leads to a lot of mistakes (just glad it wasn’t fatal! LoL). Optimism is cool but remember to be realistic and sensible.

    SMART and always do an ARK (Act of Random Koolness (TM) )

    Sipping a cup of coco,

  37. I think it’s important to keep the balance, I would echo the views of some of the others, Mastermind groups can feel uncomfortable at the time but they are constructive in the longer term

    Sometimes we need our bubble burst and other times we need that pat on the back or the alternative view on an idea that makes the difference

    Thanks for sharing Tony

  38. Thanks for this Jeff – great timing as I am about to run a vision day for our members! I was looking around for some extra inspiration and in you popped into my in-box!

  39. Great post Jeff.

    It is so often the unseen obstacles which scupper an otherwise good idea, but also common is that when you spot the obstacle you can turn it to marketing advantage before your competitors are aware of the issue. So brainstorming obstacles need not be negative it can be a positive way to a better product.

  40. Yeah, I tell ya. I’ve become terribly pragmatic in my old age of 35, lol. As it were build your boat, and let your hunting friends shoot it full of holes. If it still floats, it’s a good boat.

  41. Love the article – excellent comments as well.

    Virtually all entrepreneurs have experienced their share of failures and even out and out disasters. Optimism keeps us in the game and it has helped me to rationalize that my valleys have been valuable lessons in humility, while injecting a retrospective body of wisdom that actually buttresses the next project – ouch!

    We’d all do well to pay close attention to every experience good and bad, including those of our enterprising brothers and sisters who have crashed and burned – what factors caused their demise and how could they have handled the problems more effectively? And if it happened to them, are we susceptible as well? Probably so.

    The Internet, for instance, brings extraordinary opportunity, but also serious challenges that weren’t even in existence in the ’80’s and early 90’s. So, business continues to provide an ongoing series of fresh, critically useful lessons, and demands us to be constantly analytical and vigilant – probably part of the reason we love it!

    Your point is well-taken. There can be no sleeping at the helm, especially if we’re prone to excessive, Pollyanna-esque optimism.

  42. Joe Johnson


    Hello Jeff,
    I believe in divine timing, I’m going into contract talks next week on a big contract and I think you just saved my ??? because I would have let the big boys talk me out of the room. like I have in the past. now I can build confidence in my ability and stand firm on my solution.
    Joe Johnson

  43. Craig Burgess


    Jeff, I’m in the process of setting up my first business on my own and about to work through identifying my niche (or niches), so finding this article has been timely. I love the pragmatism and relative simplicity of this approach. What a great way to work through the options. Thank you for such a great post! Best wishes, Craig.

  44. Hey Jeff –

    When I got your email, I wasn’t quite sure where you were headed on this article…as always, you delivered.

    I shared your article with my wife because your article perfectly captured the essence of my mindset as a business operator and entrepreneur. While we always get there together, sometimes we temporarily don’t “speak the same Ianguage.” The disconnect is I work backwards and she works forwards, so initially, she sees me as “skeptical” and I view her as “overly optimistic.” Once we bang heads a little bit, we get to the “right answer” for us…

    The article was like a coconut over the head…I should have seen it coming while standing under the coconut tree, but was too busy watching the waves lap upon the shore.

    Thanks for the insight.

  45. Thanks Jeff,
    For Keeping us grounded and focused. I have been down the Mastermind Group road a time or two and what you spoke about these groups lacked, Great Piece.

  46. While I am no General Eisenhower, I am a retired colonel who as held combat commands in Vietnam, Haiti, and Bosnia. I have also managed projects, programs and product development. Along the way I have developed some opinions about optimism, hope, and planning. I agree with Jeff 100%

    My way of saying it:
    o Murphy was an optimist
    o Identify everything that reasonably can go wrong and develop contingencies for them
    o An obstacle is not a reason to quit, it is just there to keep things interesting
    o Hope is not a plan

  47. In my blog, Lessons From the Factory Floor, I talk about the Theory of Constraints as described in the incredible book, The Goal by Eli Goldratt. I ran a manufacturing company years ago. An emergency came up and I had to take over running the factory, something I knew nothing about. I was OPTIMISTIC that I could do it, but I was confronted by bottlenecks everywhere. I soon learned that every bottleneck was caused by a constraint and that in order to remove the bottlenecks I had to remove the constraints causing them, starting at the beginning of the assembly line. As I pushed the bottlenecks forward, to the end of the assembly line, there was greater productivity, until finally a complete flow of goods.

    I carried this lesson into all business: constraints WILL pop up everywhere, identify and plan for them, and even then, the unanticipated will occur, but that’s the good news. As that occurs, you simply add it to the list of what can be anticipated. I love bottlenecks because they lead to breakthroughs.

  48. Good insight, Jeff. The most successful entrepreneurs get in the habit of thinking this way. Troubleshooting and managing expectations ahead of time saves you a bunch of stress. Think of everything that can possibly go wrong so you can put fail-safe systems in place.

    Continued success 🙂

  49. One of the best reasons to discuss the obstacles first is to dig down and see if they are REAL obstacles… that cannot be overcome. Too many people create obstacles that can easily be managed. Sometimes it’s easier to give up on a big idea than to see it through.

    Check out the book: PERFORM LIKE A ROCK STAR and Still Have Time for Lunch.

  50. This speaks to one of the big problems beginners (such as I) have. We’re optimistic because the sky’s the limit. When the inevitable problems crop up, we abandon one path (because there are so many others), and we end up getting nothing done. I switched plans so many times I can’t remember them all.
    It takes digging in, finding solutions, perseverance.
    Dig in until you’re making it work. My first goal was $10 a day consistently.

  51. Great post Jeff. This is the kind of thing that more starter business owners could do with hearing. It saves time and money, and means you know how best to go about helping your customers best. I think this applies to life in many other ways too, which is the same of any fundamental principle to successful endeavors.

    Matt : )

  52. I learned it the hard way – that you MUST have several exit plans in place from the very first day. That means also having Plan B, and even Plan C. And – they should change, just like your mission and vision can change. I beg my clients and audiences to UPDATE. Great blog – thanks!

  53. Great points Jeff. Mastermind groups need to be more than a cheerleader session. We don’t do each other any favors when we gloss over obvious challenges and flaws because we don’t want to “burst any bubbles”.

  54. You hit the nail on the head. Success is a combination of being positive, having a solid plan, implementing that plan and above all making sure money can be made with that plan. Being off just a little on any component will give you headaches and lighten your wallet.

  55. Phillip Yee


    I like this post, it identifies that not everything is positive all the time, you need to look at other aspects as well when looking at building a business.

  56. Thanks for this post.

    One of the best things I’ve ever heard said about reverse engineering a process was when Eben Pagan said “Figure out all the things that have to happen so that the outcome you want is unavoidable” or something to that effect. This is a nice addition to that mindset.

    I like being a part of your community of smart people.


  57. Excellent and realistic post. I also got a lot of value from comments written above. Thanks. The old saying-“Hope for the best and be prepared for the worst” holds good in both personal and business life. It is better to be proactive and safe than be sorry.

  58. Thanks, Jeff. Great info. I always admire the people who can talk about the challenges in a positive way. Often they are challenges for competitors too!

  59. Matt Pritchard


    Hi Jeff/All,

    This strategy reminds me strongly of one that I have used to great effect on many occasions called the Disney Model. It uses the 3 separate states of mind that Walt Disney (who some would regard as fairly successful at what he did) used to develop his ideas. It can be used as an individual, small groups or large teams to great effect.

    The core principle is that you position yourself in 3 distinct mindsets for whatever project or idea you are developing. The first is CREATOR wher you develop your ideas, brainstorming as many opportunities and blue sky options as quickly as possible and without censorship. You the get yourself out of this state; shake it off; move somewhere completely different and put yourself in the mindset of CRITIC. in this mindset you allow all the negative pitfalls to flow freely. Getting the all out on paper and avoiding ‘positive’ thinking. Lastly, you shake off that state again an set yourself up in the position of REALIST. In this position you take a realistic standpoint based on the results of steps 1 & 2 and start to develop the realistic opportunity and plan.

    This concept also works fantastically well in groups where you can either have separate mini groups working in each position based on their natural strengths and thinking styles, or the whole group can position itself in each state, maybe using seperate rooms to break the previous state an using a separate flipchart to allow the ideas to develop freely.

    Hope that helps. I know it has assisted me many times personally, professionally and in my corporate positions and is also great for generally resolving problems and even conflict.

    New Leader Academy.

  60. Jeff,

    I love how you tell entrepreneurs to look at problems as obstacles, and something that you can overcome.

    “relentlessly optimistic” can sometimes get a lot of us in trouble, yet we need to balance that with believing in our dreams and following our passion.

    You give this all great perspective here.
    🙂 Christina

  61. Hey Jeff, this is something that I never even thought about doing. I’m always extremely optimistic to the point that it pisses me off when things don’t work nearly as good as I had “planned” them too.

    I’ll need to test this out with an up and coming project I’m working on.


  62. Great point! I have just added “Prepare plan B for every potential obstacle” to the TODO list for my next product lauch. Thanks!

  63. Expect failure, but plan for success.

    When I was planning my business, I looked at all the facts and realised that it was 100% guaranteed to experience continuous systemic failure from the outset and go bankrupt within 6 months. So I set up the business anyway to see if I could make it last 7 months. Unfortunately, it became successful after 4 months and I had to spend the next 5 years redesigning the business so it was able to cope with success.

    You can’t be either blindly optimistic or totally pessimistic. There’s a technique called “Six Thinking Hats” that’s useful here – it ensures that things are pondered from multiple perspectives – eg. black hat thinks of obstacles, yellow hat is optimism, etc.

  64. Never thought that thinking of negative things can bring so much help to our lives. I’m a very positive person and I always divert my attention when negative thoughts get inside my mind. However, after reading this post, I will try to think of some negative things that can be an obstacle to my life or business and defeat it as early as I can. Thanks.

  65. I think this is my biggest weakness. I believe so strongly in my ideas, they just take over and I get so bullheaded about the potential results, I come up short…..sometimes. Other times, my positiveness and not focused on the negatives has worked for me with astounding success. Appreciate the article. Thanks.

  66. Sun Tzu said, “According as circumstances are favorable, one should modify one’s plans.”

    I find that setting a timetable is helpful. Setup plans A, B and C, then set a timetable. Give plan A six months. Evaluate, change or stay the course when the time line is up. Give plan A it’s full time to develop, e.g., six months, a year, maybe two years or more.

  67. Greetings Jeff,

    You bring up a very valid point and one that should be heeded by all entrepreneurs (check that, everyone!).

    As a “recovering CEO” (and naturally optimistic person) I’ve learned to seek out folks who “call it like they see it.” I believe in “saying the unsaid” and encourage those around me to do the same.

    It’s the silent objections that always kill you (or your business). Find the people that care enough about you to tell you the things you don’t want to hear- like reality!

    If we surround ourselves with only cheerleaders it will only make for a lively wake when our business dies…

  68. Good post Jeff and great comments. Optimism can definitely be blind… then REALITY comes along and for many… their dreams get squashed & they give up.

    Learning from our failures & mistakes are the BEST lessons. We tend to listen better when we are still smarting from the last debacle.

    The takeaways from the comments above are the Six Hats & SWOT. Thanks

  69. Hey jeff,
    I use this method with every project I have , its really useful to know all the obstacles you’ll face and get ready to fix before you face them.
    Also one point is important , to make sure you 100% fix ALL possible obstacles ,then you can be optimistic as much as you want cause THERE WILL BE NO WAY TO FAIL , except laziness etc.

    Have a good day everyone , Shadi Halloun

  70. i think one of the reason people feel bad, depressed is due to the fact that they hang on negative people’s blogs, website and watch fox news. If you wanna feel positive, hang out on blogs of people like Frank Kern, Tony Robbins, Jeff, Wayne Harrel and so on.

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