Entrepreneurs lead a busy and overwhelming life, whether you’re just starting out or already leading a company – you know how much your time is worth to you. But do you know where your time goes? Turns out, most people don’t, we all end up staring at our phones way too often and wondering just how we spent all day working without really achieving much. With life getting out of hand daily, everyone wants more control over their time. This is where time management comes in, a topic much raved about but still rarely practiced. Here are ten tips to get you started:
1. Track your time
The more you know about where your time goes, the more you’ll be able to hold yourself accountable. If you’re into time sheets, block out your day in a notebook and start writing down what you spend time on. If however, you’d rather save time tracking time, try one of the time tracking tools available out there and finally get a sense of your time. Time management expert, Laura Vanderkam suggest tracking all of your time for a week (precisely, 168 hours) to get a better sense of your habits. It’s a great start and the results are bound to dazzle you.
2. Stop guesstimating
Now that you’re tracking time, you have a lot more insight into what tasks take the most of your time and how long certain tasks take. Set goals for every week and try to estimate how long will these take to accomplish. Your goal for next week will be bringing estimates as close as possible to reality. If you’ve ever worked in a management position, you know how hard it is for some people to estimate the time it’ll take for certain tasks. Now, try it for yourself and don’t worry if you’re way off – you’ll get better, that’s what time management is about anyway.
3. Plan ahead
Apparently, every minute you spend on planning saves you at least ten minutes in execution. If this sounds too good to be true – try it for yourself. Start your week on a Sunday, grab a pen and paper and think thoroughly about everything you want to achieve this week, think about bigger goals but also try to line up the steps needed. Make sure you’re ready to start work on Monday, rather than spending your morning trying to figure out where to start from.
4. Make a smarter to-do list
Don’t just list our everything that needs to be done and expect to cross things off the list as they come. Organize your list by priority, make your goals realistic, and set a daily focus for each day of the week. This will help you clear your head and make your to-do list a bit more bearable, it also will help focus and stop wasting your time on reorganizing the list.
5. Batch related tasks together
Since focus is key to productivity, be smart about the things you choose to dedicate your time to and what time of day you spend on these. If you try managing your company internal stuff while emailing investors and discussing new feature requests, you’re bound to lose focus on at least one if not all of those things. So try to divide your weekly tasks in categories – internal, fundraising, development etc. Your brain can’t do context switching full time, try to keep focus on similar tasks to stay on track and save time.
You have a team of employees depending on you, you have a hundred unread notifications on your phone, you have meetings that require follow-ups, and the cleaners also need you to let them into the parking lot once they arrive. You’re an entrepreneur, you get interrupted a lot. This is why you should never schedule your day 100%, make plans for being interrupted. This might sound counterintuitive make sure you to optimize your schedule so the interruptions don’t disrupt your entire workflow.
7. Make use of prep time
Whether it’s a meeting or a phone call – anything that might go on forever and eat out your time while you helplessly try to get back to work – plan it out. Make an agenda for every meeting or phone call you have scheduled, make sure you lay out the goals you want to achieve with this, start with an introduction to everyone involved, be a leader of every conversation you’re in, and once everybody’s gotten what they wanted from it. Start with your exit strategy and don’t let small talk take over.
8. Take breaks
Contrary to popular belief and modern business culture, breaks are not a waste of time. Breaks help restore focus and give you a fresh start for any task you have on hand. Be generous to yourself and take breaks often, don’t let the feeling of burnout get to you. Whether it’s a walk to the nearby park or a quick round of Candy Crush, you’ll feel refreshed and as good as new when back to work. Alternatively, try the Pomodoro method and see how it fits into your workflow.
9. Make use of incubation
Incubation, in terms of psychology, is one of the four stages of creativity and it starts when you’re not actively thinking about whatever problems need solving or ideas you’re trying to develop. Don’t think about work all the time. I know it might seem hard for someone that is supposed to always be working toward their goals but you’re actually more likely to get new ideas and think of solutions to problems you’re facing when you’re not actively thinking about the solutions. Many entrepreneurs boast about not taking weekends off or bringing their work home. The truth is you’re far more productive when not constantly keeping busy.
10. Calm down
Have you ever noticed how time goes by so slowly when you just calm down, clear your head and stay in the moment? Yoga, meditation, mindfulness are all methods of taking back some control over present, rather than planning for the future or thinking about the past. However, you don’t have to turn into a zen guru to feel the moment. It’s enough to try and not think about anything for a few minutes, enjoy a view, play with a pet, enjoy artwork or simply gaze at the sky. Be present and don’t let your time be taken over by the numerous distractions of the modern world and you’ll be happier and more productive in no time.
As humans, we typically operate on cognitive autopilot. We rarely stop and reflect on how we interpret information and create mental models which replicate our perception of reality.
But when our mental models fail to match reality, we simply ignore reality and operate throughout the day on implicit assumptions. These are not conscious choices. Our mental models allow us a simple way to cope with reality, yet we fail to confront reality when it is different than our mental model. Essentially, we have unknowingly created a ready-made default mechanism. 
So, what can we do?
We must first take time to reflect on our critical thinking skills. By simply understanding how you interpret and perceive information differently than everyone else is a great first step. To truly upgrade your critical thinking skills, you must examine how thoughts arise in your mind and how they got there.
Critical thinking is about asking yourself how you make choices. We can choose to believe something we hear or see; however, why do we choose to believe something we hear or see?
As a Red Team Member in the U.S. Army, I will explain how I upgrade my critical thinking skills using Colonel John Boyd’s OODA Loop as a framework for critical thinking. I will then demonstrate practical ways to upgrade your critical thinking skills for a sharper mind using tools and techniques from the University of Foreign Military and Cultural Studies (UFMCS) Center for Applied Critical Thinking (also known as the Red Team school) and The Applied Critical Thinking Handbook (also known as The Red Team Handbook).
Critical thinking can be explained in a number of ways. Let’s quickly examine a few definitions:
“Critical thinking is a process, the goal of which is to make reasonable decisions about what to believe and what to do.” – Robert Enis
“Critical thinking means developing an ever better worldview and using it well in all aspects of your life. The essence of critical thinking is questioning and arguing logically.” – Gary Jason
“Critical thinking is searching for hidden assumptions, noticing various facets, unraveling different strands, and evaluating what is most significant. It implies conscious, deliberate inquiry, and especially it implies adopting a skeptical state of mind.” – Sylvan Barnet and Hugo Bedau
To me, critical thinking is as follows:
“Critical thinking is observing the world with an open and skeptical mindset with the goal of exploring all alternatives objectively (as much as possible). It is our ability to orient our mental models to view reality through an emotionless lens seeking the truth by questioning our own assumptions and deconstructing arguments logically. It is our ability to identify gaps and uncover what is missing to improve our quality of decisions. Finally, it is our ability to unravel different strands of significant information through a continuous stream of feedback so that we continuously destroy and create new mental models allowing us to act closer to reality.” – Dr. Jamie Schwandt
Critical Thinking Framework: OODA Loop
I use John Boyd’s OODA Loop as a framework for critical thinking. It is similar to Swarm Intelligence, where we use simple rules to allow the collective intelligence to emerge. The simple rules are Observe, Orient, Decide, and Act.
The OODA Loop is a high-speed decision making and feedback process in four stages: Observe, Orient, Decide, and Act. The OODA Loop is a continuous feedback loop where the objective is to go through the loop faster than your opponent.
I use simple rules provided within the OODA Loop to assist me in speeding up my critical and creative thinking abilities. However, do not confuse the word “simple” with “simplistic” as the OODA Loop uses simple rules within a complex system (which is exactly what the OODA Loop is).
The key to the loop is feedback. The OODA Loop is similar to Double-Loop Learning, where the goal is to modify decision-making in light of new experience.
Double-Loop Learning is the first loop uses goals or decision making rules, the second loop enables their modification… hence, double-loop.
Chris Argyris writes about Double-Loop Learning in Teaching Smart People How To Learn,
“A thermostat that automatically turns on the heat whenever the temperature in a room drops below 68 degree is a good example of single-loop learning. A thermostat that could ask why am I set to 68 degree? and then explore whether or not some other temperature might more economically achieve the goal of heating the room would be engaged in double-loop learning.
The overarching guide for my use of the OODA Loop is as follows:
I will talk about this more in the How-To Guide: Tools to Apply the Critical Thinker’s OODA Loop section below.
It’s about seeking truth. Here we should seek to follow a concept introduced by Immanuel Kant as a way of evaluating motivations for actions – called the Categorical Imperative. Kant defines a categorical imperative as an absolute or an unconditional requirement that must be obeyed in all circumstances and is justified as an end in itself. For example, “Act only according to the maxim whereby you can, at the same time, will that it should become a universal law.” For more information, visit the Categorical Imperative.
This is essentially solving problems by working backwards. A simple example of this method is working backwards to solve a math problem.
For example, solve the following problem: “I think of a number and add three to it, multiply the result by 2, subtract 4 and divide by 7. The number I end up with is 2. What was the number I first thought of?” To solve, read the problem backwards. You start with: 2 x 7 = 14. Then take 14 + 4 = 18. From there take 18 / 2 = 9. Then take 9 – 3 = 6. Finally, the number you first thought of was 6.
Moreover, Reasoning Backwards can be viewed through the lens of deduction. I prefer deduction over induction and here is why:
An example of Inductive Reasoning is: this raven is black, that raven is black, all ravens are black.
Deductive Reasoning is: All ravens are black, that raven is black, therefore it is black.
We make deductions from laws to see what should happen and then experiment to see if our prediction was right. Think about it this way… to test whether a burner is hot, we must touch the burner first using Inductive Reasoning; however, if we were to use Deductive Reasoning, we would first predict the burner to be hot and would realize there is not need to touch it.
One last benefit of Reasoning Backwards is that it forces our linear and logical mind to catch things we wouldn’t normally catch. For example, read the following sentence:
After reading this sentence, you will realize that the the brain doesn’t recognize a second ‘the’.
Now read the sentence again, this time read it backwards. Did you notice that you missed the second ‘the’?
The UFMCS uses this as the single most important idea to enable critical thinking. For example, prior to taking on an issue, we should first think independently and reflectively, then write down our thoughts (which assists us in shaping and refining them), then share them in a disciplined manner. This takes us from divergence to convergence.
Boyd described a thought experiment in a presentation called Strategic Game of ? and ?. Through the process of Destructive Deduction (analyze and pull apart mental concepts into discrete parts) and Creative Induction (using these elements to form new mental concepts) we can create a new mental model that more closely aligns with reality.
Part 1 of his question:
“Imagine that you are on a ski slope with other skiers…that you are in Florida riding in an outboard motorboat, maybe even towing water-skiers. Imagine that you are riding a bicycle on a nice spring day. Imagine that you are a parent taking your son to a department store and that you notice he is fascinated by the toy tractors or tanks with rubber caterpillar treads.”
“Now imagine that you pull the skis off but you are still on the ski slope. Imagine also that you remove the outboard motor from the motorboat, and you are no longer in Florida. And from the bicycle you remove the handle-bar and discard the rest of the bike. Finally, you take off the rubber treads from the toy tractor or tanks. This leaves only the following separate pieces: skis, outboard motor, handlebars and rubber treads.”
What do you imagine could be created using the remaining parts? A Snowmobile
Let’s now turn our attention to the four simple rules within the OODA Loop.
The Critical Thinker’s OODA Loop: Simple Rules to Guide You
Think of how we use sensors and gather information. In an ant colony, this is where ants shoot pheromones to signal others when they have found food.
Here we are detecting events within our environment and identifying change (or lack thereof). This could also be identified as Locate or Perceive (think swarming tactics or artificial intelligence).
Find out what is really there.
Observe first and gather data.
Identify the uncommon and common things. As Sherlock Holmes famously said, “What is out of common is a guide.” A great video on this point is The most unlikely threat from the hit movie Men in Black – watch the following video:
Begin with a blank and open mind.
Remember that there is nothing more deceptive than an obvious fact.
Key questions to ask:
What are we being asked?
What do we know?
Key tools to use:
6 Words. This is simply writing a short and precise phrase summarizing your thinking into a set number of words.
Key assumptions check. We all start with assumptions and it is extremely important to be aware of our own. Understanding this will allow us to explain the logic of an argument and expose faulty logic. It will also help us simulate thinking about a problem and uncover hidden links between factors. Let’s examine some key questions to ask here: 1) How much confidence do you have with this assumption?; 2) What explains your confidence with this assumption?; 3) What must exist for this assumption to be valid?; and 4) If this assumption proves wrong, will this change your line of thinking about the issue?
Analysis + Synthesis. By breaking a concept or problem apart (analysis) we develop knowledge; yet, it’s when we piece the parts back together (synthesis) and create something new that we develop understanding or wisdom.
Onion Model. Hofstede’s Onion Model is a great tool to find values at the core. It is a great way to prompt better questions, look at something or someone or some group from multiple perspectives, and expose ignorance.
neXt – Innovative Framework. Professor Ramesh Raskar, head of MIT Media Lab’s Camera Culture Research Group, created an easy-to-use framework for inventing the future – right now. Watch the following video:
Think of a hypothesis like you would when putting a puzzle together, where you are making predictions then testing those predictions.
Devils Advocacy. Here you are trying to prove the opposite and disprove the hypothesis. Essentially, you are trying to prove the limitations.
Alternative Futures Analysis
Analysis of Competing Hypotheses (ACH) (see below)
The Value of Possible. Here is a logical system incorporating elements of language. In this method, we have three truth values: False, True, and Possible. Logical connective rules: True is p, Possible is q, and False has no value. This allows for something to be fuzzy (not clearly black or white… true or false) but could still be true.
Think of testing and retesting a hypothesis.
According to Boyd, actions should be rapid, surprising, ambiguous, and ever changing. This could be identified as Disperse or Learn.
Carry out your decision (or selected action) while the opponent is still observing the last action.
As Sherlock Holmes said, “Nothing clears up a case so much as stating it to another person.”
Develop quick “fly-like” reactions.
Use simple rules to guide your actions or the actions of a group.
Find the desired path. For example, watch how routes on a college campus naturally form. Wouldn’t it be interesting if we allowed these to naturally form then simply pave those locations. For more on this idea, watch the following video Find and Pave the Desired Path:
Key questions to ask:
What did I learn?
What type of feedback did I receive?
What type of feedback am I still receiving (we are continuously receiving feedback)?
What can I do with this new information as my OODA Loop begins again?
The UFMCS provides a powerful framework for deconstructing an argument.
What is the argument? Here the argument = problem (or premise) + reasons + conclusion
Check to make sure the right problem is identified and examine the point of view of the other person.
Search for and ask for clarification of ambiguous words.
Look for value conflicts and check key assumptions. More specifically, look for prescriptive assumptions (statement made on the way things should be) and descriptive assumptions (statement made on the way things are).
Check the evidence provided. Does the person use personal experience, potentially deceptive statistics (use numbers without percentages – percentages without numbers), appeal to authorities, faulty analogies, intuition, etc.
Is there another plausible hypotheses which might explain the situation?
Are there any other conclusions you can draw from the argument?
What implications does accepting the argument pose?
2. The 4 Agreements
Another great way the U.S. Army Red Team community upgrades their critical thinking ability is through the following four agreements:
Don’t make assumptions.
Don’t take anything personal.
Be impeccable with your words.
Always do your best.
Finally, I recommend using the following mnemonic. I created this tool to assist me as I move through the Critical Thinker’s OODA Loop. Additionally, I recommend writing this down on a note-card and keeping a copy with you at all times.
Think like a Scout – the drive to see what’s really there.
In the following video Why you think you’re right-even if you’re wrong, Julia Galef examines the motivation between two mindsets (Scout mindset vs Soldier mindset) and how they shape the way we interpret information:
Galef explains that Scouts are curious and are more likely to feel pleasure when they learn new information. She says it’s like an itch to solve a puzzle. We should strive to develop a Scout Mindset. Let’s examine qualities Scout’s possess:
The Scout’s job is not to attack or defend, but to understand – to go out, map the terrain and identify potential obstacles.
Scout’s are intrigued when they encounter something that contradicts their expectations.
More likely to think it’s virtuous to test your own beliefs.
They do not say someone is weak for simply changing their mind.
They are grounded; meaning their self-worth isn’t tied to how right or wrong they are about an argument.
They are proud (and not ashamed) when they notice they might be wrong about something.
They are intrigued (and not defensive) when they encounter information that contradicts their beliefs.
They yearn not to defend their beliefs, but to see the world as clearly as they possibly can.
Above all, the Scout seeks to know what’s really there.
Find the Dog who isn’t barking.
In Arthur Conan Doyle’s Sherlock Holmes story Silver Blaze, we are presented with a mystery of the disappearance of a famous racehorse the night prior to a race and the murder of the horse’s trainer. Mike Skotnicki describes the story about The Dog that Didn’t Bark:
“The dog that didn’t bark. What we can learn from Sir Arthur Conan Doyle about using the absence of expected facts.” – Mike Skotnicki
Sherlock Holmes solves the mystery in part by recognizing that no one he spoke to in his investigation remarked that they had heard barking from the watchdog during the night.
Gregory (Scotland Yard detective), “Is there any other point to which you would wish to draw my attention?”
Sherlock Holmes, “To the curious incident of the dog in the night-time.”
Gregory, “The dog did nothing in the night-time.”
Sherlock Holmes, “That was the curious incident.”
The fact that the dog did not bark when we would have expected it to while the horse was stolen led Holmes to the conclusion that the criminal was not a stranger to the dog, but someone the dog recognized; thus, would not cause the dog to bark.
What would have to exist for something to be true?
Here we can use a UFMCS Red Team tool called What If? Analysis. This tool assumes an event has already happened with potential impact (positive or negative) and explains how it might play out. This is a powerful technique for challenging a closed mindset by shifting the focus from whether an event could occur to how it might happen.
Clearly state the conventional line assuming the event has happened, then step back and consider what alternative outcomes are too important to dismiss, even if unlikely.
Select triggering events that allowed the event to happen.
Develop a chain of argumentation.
Reason backwards from the event in concrete ways (specify what must occur at each stage).
Choose one or more plausible pathways.
Develop and monitor a list of indicators or observables for each scenario that would assist in detecting the beginning of the event.
Another technique you can use here is The Reductio ad Absurdum. This is a simple yet powerful tool.
Assume a statement to be true and see what conclusions you can discern from it. If you find you get a contradiction, you know the initial statement is false as contradictions are always false.
It allows you to determine if a statement is false by showing the contradiction.
Here we can use a combination of tools and techniques.
For example, if you have a team or group of people, you could use what’s called a Premortem and/or Postmortem Analysis. This is an application of mental stimulation and is a great tool for Group Think Mitigation. We could use the 5-Why technique after we have asked what happened. We could also use Algorithmic Thinking where we perform an If-And-Then series of questions.
Let’s combine the three and see how this can be used:
Assume an event has happened or after an event has happened – use 5-Why to identify causes as to why this event happened.
Generate a list of reasons for the event with the following simple rules: 1) The more ideas the better; 2) Build on other peoples ideas using them as prompts for your own; 3) Wacky ideas are fine (and sometimes preferred).
Ask a series of If-And-Then questions:
IF an Active Shooter is spotted AND appropriate signals are in place THEN we should be able to act/respond quicker.
This can also be used with Propositional Calculus. For example, “If you are a bird, then you have wings,” could be rephrased as, “You cannot be a bird and not have wings.” It is a proposition using one connective such as: IF-Then. It can then be transformed into an expression using the other connectives “and” and “not” without changing the validity of the statement.
Ask what evidence is not being seen, but would be expected for a hypothesis to be true.
Conduct an Analysis of Competing Hypotheses (ACH). The objective is to identify alternative explanations (hypotheses) and evaluate the evidence that will disconfirm rather than confirm the hypotheses. This is how I reason backwards.
Brainstorm and list all possible hypotheses (no matter how improbable they may seem). List the hypotheses first then the evidence (think deductive reasoning). You can list the evidence first, then the hypotheses if you prefer (think inductive reasoning).
List all significant evidence and arguments relevant to each hypotheses.
Reason backwards by creating a divergent systems diagram with each hypotheses from right to left (to mimic backwards reasoning)
Start to converge by preparing a matrix listing the hypotheses across the top with each piece of evidence down the side.
Determine if each piece of evidence is consistent, inconsistent, or non applicable.
Refine the matrix by reconsidering each hypotheses. Here you can even add new information if applicable.
Focus on disproving each hypotheses rather than proving one. Tally your evidence that are inconsistent and consistent to see which hypotheses are the weakest and strongest (you can also identify this using your systems diagram… +/- for strong and weak connections).
Ask what evidence is not being seen, but would be expected for a given hypotheses to be true. Ask if denial and/or deception is a possibility.
Identify and monitor indicators that would be consistent and inconsistent with each hypotheses.
Where are the Pattern (or location) of bullet holes NOT located?
Statistician Abraham Wald was tasked with helping the Allies decide where to add armor to bombers during World War II. The Allies hoped extra protection would help minimize bomber losses due to enemy anti-aircraft fire. They thought the answer was obvious and the bombers returning from missions showed them where to put the extra armor. However, Wald disagreed. He explained the damage actually revealed the locations that needed the least additional armor. In essence, it’s where the bombers could be hit and still survive the flight home.
This is an example of selection or survivorship bias, where we typically only consider information that’s presented to us and ignore information that is absent, yet might just be significantly relevant. For example, the locations on the bombers without bullet holes might just be the location to reinforce.
Finally, we should be extremely carefully of what we remove from a system or process. We have to be aware of the second and third order effects.
I will leave you with one final video: How Wolves Change Rivers: