The Invisible Work That Drives Success

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The Business You Really Want | Strategic Thinking

Feeling too busy to think strategically? You’re not alone. In this episode, Tonya Kubo and Gwen Bortner tackle one of the biggest challenges facing modern business owners: finding time for strategic thinking when everything feels urgent.

Discover why strategic thinking often feels like “not working” and how this mindset keeps us trapped in reactive mode. Gwen shares practical strategies for building strategic thinking as a skill, starting with just five minutes a day, and explains the difference between strategic and tactical questions.

You’ll learn how to shift from being pulled by circumstances to proactively choosing your direction, plus get specific thinking questions you can use to start practicing strategic thinking immediately.

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The Invisible Work That Drives Success

The Challenge Of Making Time For Strategic Thinking 

If you’re so busy and you barely have time to think, this episode is for you. My name is Tonya Kubo. As always, I am here with Everyday Effectiveness founder, Gwen Bortner, to talk about one of the biggest challenges facing modern business owners. It’s not the economy, not regulations, and not policy, but time. More importantly, it’s time spent thinking strategically about the business.

Gwen, during our show anniversary series of episodes 53 through 56, for those of you who are new here, something kept bubbling up in our conversations. We were talking about the vital role that strategic thinking plays in a business’s success and how the best person to do that work, the founder or CEO, often isn’t doing it. Why do you think that is?

That’s because there’s so much else to do, and all of those other things, like check off a box of some sort. I don’t know about you, but I love the checkbox. Talk about a dopamine hit. It’s the dopamine hit when you hit all of those things. Combine that with thinking time feels like not working.

It does not feel like work.

Put those two things together, and there’s no surprise that it’s not high on people’s lists.

In the past, you’ve said something that I’ve always thought was interesting. I’ve heard you say this to clients before. It’s that women especially equate being busy with being productive.

Women are extra, but it is very much a societal thing. If we’re not actively doing something, we’re not productive, which is not true. It’s not even close to true, but it feels that way. If you’re old like I am, your parents’ generation was all about hard work. You need to be a hard worker. You need to be a good worker. That was about activity. Being a good thinker was important, but only so that you could do more work more effectively. We’ve shifted some over time, but there’s still that whole Puritan work ethic. All of that is still well into our whole systemic lives.

Old habits die hard. That’s a fact. The points you made, though, are that strategic thinking tends to produce ideas. It produces some insight. It might shift your thinking on what direction you should take, which aren’t things that are easy to check off a list. I am younger than you, but I still remember a time when, in school or my early career, you were always recognized and rewarded way more for output than you were for the thought process that got you to the output.

That’s true.

That ends up creating a situation where if you’re a business owner over the age of 40, but maybe over the age of 35, you end up feeling guilty when you’re spending time quietly thinking, strategizing, journaling, or whatever, because you’re thinking, “What I should be doing right now is serving my clients. I should be making sales. I should be fixing problems.” That is all tangible, good dopamine hit stuff versus thinking, “What is the offer that I should cut to get to where I want to be next year?” or “What do I want out of my business in the next five years, and how do I want to get that?”

Gaining A Clearer Understanding Of Strategic Thinking 

There’s something else, though. I’m not sure the average person, or at least the average business owner, knows what strategic thinking is and what it isn’t. A lot of people view what you or I would refer to as strategic thinking as daydreaming. I hear this a lot. I had a conversation with a mutual client where they labeled it as procrastinating. They were like, “I’m procrastinating.” They were thinking they were procrastinating to avoid the real work that needed to be done. I’m like, “You’ve got some big decisions to make before you even know what the next right step is.”

There is this perception that strategic thinking happens in this very quick, focused way. That’s not true because strategic thinking is looking at lots of options, considering what they all are, and trying to anticipate the outcomes of what any one of those particular paths would be. That’s where we start getting strategic to say, “I’m making a specific choice out of these two, three, five, twelve, and it doesn’t matter how many options, with the anticipation that that’s going to result in A, B, C, D, which is going to get me to this point that I want to be. I also understand I could choose option 2, but it’s going to take more money, but it’ll be less time, and option 3, which would take more time but less money.”

It’s thinking through that bigger picture of what I am sacrificing and what I am gaining based on any particular choice. That isn’t done as a quick activity. Being able to get into a space to be able to do that for a lot of us is hard. For some of us, it’s a very easy process. Our brain gets there pretty quickly. For others of us, it’s hard. For a lot of my clients, part of the reason they work with me is that we can have those strategic conversations, and they know that we will take the time to have the strategic conversation. It’s a way that helps make sure that it gets done.

That’s part of the work. Strategic thinking is intentional time spent pulling yourself out of the weeds to examine your business. In the case of you working with clients, you’ve created the space for them. You’re like, “This is the hour we have. We’re protecting the time. This is what we’re going to do there.” The nice thing is when you’re doing it with somebody else, you can’t talk yourself out of the productivity of it.

You can’t talk yourself into, “Do you know what would be better right now? It would be better right now for me to make my grocery list. It would be better right now for me to meal plan for next week, catch up on email, and double-check my invoices.” All of those things make us feel good. We’re like, “I know. We should post some stuff to social media. That’s what we should do right now.” They can’t do that when they’re face-to-face with you. First of all, they wouldn’t because that would be rude. Second, if they tried and they said, “This is what I should do right now,” you would say, “The time and the space are for this.”

Exploring Real-World Examples Of Strategic Thinking In Business

I’m curious about your experience. Could you give us some examples of strategic thinking? You talked a little bit about what it’s not and talked at a high level about what it is, but I think some people don’t know what they should be doing. I’ll give you one, and then you can build off mine. When I am doing that in my own business, the first thing I’m looking at is what’s working out of everything I’m doing, and what is draining my resources? What feels like a lot of work, but not a lot of payoffs?

It’s a combination of always asking yourself what I’m going to call harder questions. They aren’t necessarily hard questions, but they’re harder questions that don’t have a super easy yes-no quick kind of thing. The question you asked could be a strategic question, or it could be a non-strategic question. If you know that this thing is not selling and takes a ton to do, “I’m going to ask myself the strategic question,” and instantly, you know what the answer is. That’s not a strategic question. That’s just confirming the strategy you’ve already decided on some other time ago. Now, it becomes a tactical question to say, “How do I get rid of it?”

If the answer is easy, it’s probably not strategic. To me, it’s about considering options. When there are options, the answer is not easy. The same question could be highly strategic, where it’s like, “I’ve got these three offers, and they all fundamentally have about the same profit margin. I like them all for different reasons. This one may produce more money, but this one’s easier to sell.” That’s when it becomes a strategic question. Part of it is whether I need to get rid of any of them, or not? Do I need to consolidate them? Do I need to reframe them? When the question gets more complicated, it tends to be a more strategic question because it’s not an easy answer.

When there are options, the answer's not easy. Share on X

It is also only strategic if it’s saying, “How is this going to affect my future? If I offer X, how does that affect the future? Does that leave a hole in my offerings, or does it make an opening for this other offer that I want to put in? Is the whole a good whole, or is the whole a bad whole?” These are the more strategic kinds of questions that we want to start to ask.

To be able to live in the ambiguity of it is when we’re starting to get into the strategy part. It’s like, “I’m willing to live in the ambiguity of this.” I was having a conversation with one of our clients. You and I talk about this a lot. I don’t think we’ve said this on the show, but we often get caught looking back at decisions we’ve made, and we say, “If I had done this other thing, it would have been better.”

My answer is we never possibly know whether or not it would have been better. We only know it would have been different. There are lots of things that would strongly imply that it would have been better. If we’re looking at likelihoods and percentages, maybe the better percentage is very high. Back to the whole context matters, even in this, there are other little tiny details that we don’t know.

Let’s say we were raised at the exact same time and in the exact same school, did all the same things, and we are best friends. You choose X and I choose Y. Somehow, your life looks so much better than mine. If I had chosen X, would my life have been better, too? No. It would have been different. To me, part of the strategy is when you’re thinking strategically, we aren’t getting wound up in better or worse, but the how and the why.

We made this choice. It had this outcome. We expected it to have this other outcome, which wasn’t. What were the variables that we weren’t able to plan for or that we weren’t aware of that we should be planning for? The more that we do that, the better we start getting at strategy because we start thinking more and more about the variables.

Understanding The High Cost Of Skipping Strategic Time

That’s a good summary of what strategic thinking is, isn’t, and how to start doing it for yourself. What do you think we lose when we skip that strategic time? You’ve seen this as well as I do, where people are like, “I don’t have time to think.” I’ve seen you ask clients or prospective clients those questions, and they wanted to kick the can down the road a bit. They’re like, “After this big deadline or after this event, I’ll circle back to that.” What’s the cost trade-off on that when you’re putting it off?

The first thing is that tomorrow never comes. We never achieve tomorrow. The cost is that we miss opportunities because we’re in a reactive mode instead of a proactive mode. It’s not that we shouldn’t be reactive. I’ve had people who were like, “Being reactive is bad.” Being reactive is also a very important skill because things will happen, and we need to be able to make choices in a short period of time.

To me, that is very much a reactive mode. When everything is reactive, then we are being pulled by the ocean currents instead of deciding on our destination. I’ve seen it with different clients who are much more strategic in their thinking. They typically seem to have way more opportunities than the clients who are less strategic in their thinking.

When everything's reactive, then we are being pulled by the ocean currents instead of deciding on our destination. Share on X

I believe that the number of opportunities is exactly the same. It’s whether or not they have the capacity to consider the opportunity, see the opportunity for what it is, and evaluate it to choose yes or no. I’m not saying that we’re taking every opportunity. As opposed to those who are reacting, by the time they get to the opportunity, they have usually eliminated so many other possibilities that it’s not a choice of yes or no. It’s going to be an obvious yes or no.

In the way to do that, a lot of times, you are investing time and money in things that aren’t working. It’s quite easy to be reactive, and it’s hard to be proactive. That’s a different part of your brain. Some people are wired naturally to be proactive thinkers. A lot of times, when you’re in business, especially if you’re coming up from doing everything yourself as you start to grow and expand, what we forget is that it’s hard to continue growing if you’re not planning for what’s next.

 

The Business You Really Want | Strategic Thinking

 

This isn’t a great example, but this happened. I was meeting with one of my long-term contacts that I’ve had, someone who can be a good resource for a lot of our clients. As we were talking, it came to me this project that I’ve been working on internally. It’s not anything that you or Sophia have been aware of. There’s no reason for it because a lot of it will take my brain. I realized, “She could probably help me with that.”

It was like, “I could strategically invest relatively few dollars to let her do the backend piece of this.” I’m more than capable of doing it. I know that I can, but it goes back to, “Is that the best use of my time right now?” There’s an element only I can do because there’s a piece that I’m evaluating, and it’s based on my experience. I can’t hand it off to you. I can’t hand it off to Sophia. I can’t hand it off to her.

We cannot evaluate for you.

Can we get it into a position that becomes even easier for me so that that’s the only part I’m doing? Instead of just reacting to the problem, I started thinking strategically about it. Part of the strategy for this is that I will have also worked with her, so when I’m making that recommendation, I can talk about what it’s like to work with her. It wasn’t just a reaction of “I’ve got this problem. Here, you can help me with it.” It’s a strategic move for me to do this.

It’s not such a huge investment that if it goes terribly wrong, I’m going to be like, “I can’t believe I spent this much money on this.” It’s strategic there. I’ve evaluated how much I am willing to lose if it goes completely wrong, what the upside is if it doesn’t go completely wrong, and what the longer-term benefit of knowing what that working relationship is like with this person is. Strategy could be seen as a tactic, but really it is a strategy because there was way more thought into why I asked her about doing this project.

Making Strategic Thinking Legitimate Work

That’s such a good example. That also helps move to a different aspect of this conversation. What I was going to ask before you gave us that example is, how can we, as business owners, make strategic thinking feel like legitimate work? You gave a prime example of how you legitimized this process of strategic thinking here. What else, though?

I’m imagining that someone who’s struggling with this is caught up in a very strong work ethic. I don’t think it’s so much a mindset issue in that they feel like they can’t delegate to others because they think they’re too good for the work. It’s not that. It’s that they’ve got a super strong work ethic. Strategic thinking doesn’t feel like legitimate work.

It also depends on whether you are task-based or big vision-based. Technically, when I test on any of those, I test under the big vision side, but barely. I’m a task-based person. I don’t know how I would evaluate my own work ethic. I used to always say I use laziness to my advantage. That’s how I always consider how I became very effective. I am task-based. For me, this thinking time is seemingly hard as well. One of the tricks that I have used is to say, instead of making it a big thing, start by making it a small thing, so that you don’t feel like, “That’s two hours that I’ll never get back out of my life.” It can feel that way, especially early on, until you start seeing where the benefit is.

The other is that if you can learn to think strategically in small amounts, it allows you to be strategic on the fly. I did not go into that call with this strategic thought process at all. It came as part of the conversation in the process that I was able to jump to a strategic approach when I saw an opportunity for that to be able to be open. Not having to have everything in my strategic mindset is also a key to it.

 

The Business You Really Want | Strategic Thinking

 

One of the first things is to think small. Thinking small can be journaling. There are a number of different examples. People have talked about doing daily pages. Daily pages can be a strategic process. My friend, Mark Levy, wrote a book called Accidental Genius, which is another version of daily pages. It’s just writing to get your mind out of the minutiae and into the other. It’s often inspired by a question.

Another interesting book is called The Road Less Stupid. It’s a little more patriarchal than I would potentially like, but at the same time, the points are valid. It is that almost anything that you regret was a decision looking back, where it’s like, “That was not the best decision, given the information I have now.” Sometimes, that wasn’t the information you had then.

He talks about taking time to think if you have a list of thinking questions. Both he and Mark approach this from similar aspects, which sometimes is asking the obvious question, like, “What is my best mix of product, given the product that I have now, the value, and all of those things?” Sometimes, it’s asking the not-obvious question or the opposite question, which is, “I hate all of my products,” even though that may not be true. It’s like, “What should I build today?”

It could also be, “What are the things that I hate about my products?” We usually don’t think about the things that we hate about our products. We think about the things we love about our products. That gets our mind into a different space. That’s the key to strategic thinking. Can we get our minds into a different space? Our friend, Nic Peterson, uses the term open-loops. Part of the reason we struggle with strategy is Nic’s open-loop concept. We have been taught, as part of our upbringing in school, that there is an answer, and that the important thing is to know what the answer is instead of allowing lots of answers to come and to figure out which one is best.

The open-loops thing is hard.

It’s terribly hard. I suck at it, just FYI. I’m having to train myself hard, and I’m paying a lot of attention to it. I was an excellent student. I always had the answer. Open loops are about not having the answer. It is so counterintuitive. I also find it very valuable.

The Accountability Advantage In Strategic Thinking

I see your calendar. We organizationally practice the same accountability process that we walk our clients through. Because you’ve been working on some bigger things, I see that you have blocked time in your calendar, like it’s a meeting, for strategic thinking, to think about some of these bigger projects and bigger visions.

Ask me how many times I hold to it.

I was going to get there. I wanted to illustrate what you mean when you say that you were bad at it, and you’re getting better at it. The first step was to block the time. There was a time when you were like, “I got to do this thing. I need to think about this thing,” and it wasn’t happening. You were then like, “You’ve got to hold me accountable to this.” I’m like, “How would I do that? How do I hold you accountable to the statement, “I have to do this thing.”

You started blocking it in your calendar, and I’m like, “Look at Gwen there. She’s got these nice two-hour blocks. Good for her.” We have a documentation process that’s part of our weekly accountability. It was in that process that you were like, “I’m not protecting that time for the things that I need to do. Now that I’m setting aside the time, I’m hyper aware of how much of that time is not being spent doing that thing.”

You gave me something actionable that I could hold you accountable to, which is that I have learned that I do have to check in. It’s like, “Supposedly, you had ten hours of strategic thinking time this week. How did that go?” I say, “I don’t want to bump into your block here,” and you’re like, “It’s because I haven’t bumped anything else into that block this week, Tonya.” That accountability process we also go through is that every week, you’re able to keep a record of what has come up during that strategic time when you have taken advantage of it and what has gotten in the way. You are getting better at it every single week.

It is about making choices and trade-offs. Sometimes, it’s like, “I’ve got too many other detail-y things that need to be done. I need that block of time to get that work done.” It is about being aware and saying, “I am making a choice about what I’m doing with it,” and deciding how I’m going to use that time. I would not recommend ten hours of strategic thinking time for most entrepreneurs or anyone, probably. That’s a lot of thinking time.

Part of my strategic time is also doing the strategic activities associated with that process. One of the things that I am trying to do is isolate at least an hour once a week to just think. I’m not doing the work that’s associated with the strategic activities that we’re trying to do for the business, but I just think. In some weeks, I do better than others. It’s the reality of it. It is a practice. That’s the important piece to get here.

A few years ago, the idea of thinking for an hour would have been impossible for me to even imagine. I’d get the heebie-jeebies just thinking about it. Over time, I have been working on doing thinking time in smaller bits. That has allowed me to get thinking time into bigger bits, which allows me to get to that place. I’ve been approaching it like a practice. I am doing intentional practice to get better at it. When I first started, most of the things that I would think about were very tactical things. I would have tactical things that are like, “That’s an interesting strategic thought.” You build it over time, and then very quickly you’re like, “That’s tactical. This is strategic.”

The Compound Effect Of Strategic Thinking

What you’re talking about is the more you do it, the better you get. There is a compound effect to it. The more you do it, the better you get, which means you get better at making decisions, in general, across the board. I have noticed that you may be trying to focus on strategic thinking in your professional life, but it also helps you make better decisions faster in your personal life.

The more you do it, the better you get. Share on X

It’s a skill.

That clarity lets you make choices faster and more confidently than you did before across the board. It’s also a way for you to increase efficiency in an effective way. Faster isn’t always better, but figuring out what is a waste of time and what’s worth the time. The more time you spend strategically thinking, that happens.

Something that I’ve seen you do firsthand is that it helps you get better at anticipating problems before they arise or before they get too big. That’s something we’ve talked about a lot. We’re like, “This isn’t a problem today, but if this keeps going like it is, this will be a problem three months from now.” Ultimately, all of that adds up to what you said a moment ago. It creates the space for opportunities so that you are not constantly managing problems. You are seeing the opportunities, you are recognizing them, and you are able to make the decisions to act on them.

Your Practical Homework Assignment For Strategic Thinking

I want to tie this up with a bow as we’re about out of time. I want you to give us some homework here. We’ve already established that this does not come easily to most of us. It is something that we have to practice. For the person who’s like, “That all sounds fine and good, but where do I begin?” What do you suggest?

I encourage you to come up with your own list of thinking questions. I have a page that I keep in my planner. These are not necessarily good generic questions, but one of the things I do with my planner is, from time to time, I’m in another environment. It could be a networking environment or whatever. Someone asks a question, like, “That would be a good thinking question.” I write it down for later to say, “That’s a good thinking question. I should take that and use that.”

An example of that is where I got a thinking question from another conversation, and I’m not saying this is your best one, but as an example of that, the question that I wrote down was, “What would I tell myself as a business coach to 10x my business today?” I’m not saying that’s a great question for everybody because not everybody may want to 10x their business.

The question about asking about 10x-ing your business eliminates a whole lot of other things. Even if you don’t want to 10x, asking yourself the question will also help you focus, like, “What are the things that I can do that are highly profitable, will grow things, and will do the things that I want?” That’s an example. I got that question from somebody else. I very quickly wrote it down so that I had that.

Here’s another one that I think is a good thinking question. “How would I start today if I had all of the knowledge and experience but none of the baggage?” I know everything I know. I have all of the experience. I have no debt, no employees, no offer, nothing. What should I do today? That’s a big thinking question. It doesn’t mean you need to take action on any of the ideas that you come up with at all. That’s the important piece.

We think that if we’re investing in thinking, then whatever comes out of the thinking, we have to do. Not necessarily. This is back to the open-loop piece. Sometimes, it’s like, “That gave me a thought that I’m going to leave as an open loop. I won’t start figuring out how to implement it and what I should do, but I leave it as an open loop to then come back to and say, ‘I don’t want to do X, but I could Y,’ which is like X but a little bit different.” That’s where we can start getting into the strategy, seeing the opportunities, and doing some of the other things.

This is another similar question but on the opposite side. “What are the things that I hate about my top three competitors? What do my top three competitors do that I hate?” That helps you get clarity about what things are important to you. Things that you hate have strong emotions associated with them. As you look at that list, you should be like, “What’s the opposite of that?”

These are three examples. They are not necessarily the best examples in the world. It is about asking yourself tough questions. Both Accidental Genius and The Road Less Stupid have a lot of examples of good thinking questions. You can probably put the prompt into AI and come up with a whole bunch of interesting thinking questions. Don’t ask AI to answer them. That’s not doing the thinking.

Do not ask AI to think for you. You gave us three good ones, but let’s go back to this person who either isn’t doing it at all, maybe not doing enough of it, or not doing it consistently. How much time do you think they should set aside as they’re non-negotiable for strategic thinking?

Do not ask AI to think for you. Share on X

Five minutes.

Five minutes a day, five minutes an hour, or five minutes once a week?

Five minutes a day as a starter. That’s how I started with my thinking questions. I would give myself a question in a journal, set my watch for five minutes, and start writing. This was Mark Levy’s method in Accidental Genius. You write the entire time. Even if you have nothing to write, you say, “I have nothing else that I can think about and write about.” You write the entire time, even when it’s completely useless and stupid. You keep writing because at some point, the mind will kick back in and you’ll have more things to write.

My thing was I would write for five minutes. Once a week, I would go back and look at what I wrote. I didn’t evaluate it then. I just let it go. Once a week, my five minutes were spent reading what I wrote the previous week, making my own notes out of it, and saying, “This was an interesting idea,” or “That made me come up with another good thinking question for another session.”

That allowed me to realize that the thinking time was valuable. It was a small enough piece that I was willing to sacrifice it, but it got me trained to see where the thinking time was valuable. After I had done it enough, I was okay with saying, “I’m going to set aside 30 minutes or 1 hour,” because I see where the value is. I’m not necessarily doing the same exercise, in the same way, going forward, but it allowed me to start seeing where that was valuable.

That is an excellent tip. Five minutes a day every day. At the end of the week, go back through everything, pull out what is meaningful and important, and maybe add some more thinking questions to the list to then give yourself evidence that this is a legitimate exercise. This is doing something for you. Rinse and repeat week after week.

You’re going to need to do it for a number of weeks because it’s hard to get our minds to shift. One week, when you look at the previous four days, you’ll be like, “This was stupid. There is nothing of value here.” That will happen from time to time. It’s one of the things that Mark points out in his book. He says, “I’m not saying that when you sit down to write, you will have your genius thought, but if you do it consistently, you will have your genius thought.”

We are out of time. That is a perfect place to leave it because it proves the point that strategic thinking isn’t a luxury to put off for some eventual day down the line when things slow down and the world is perfect. It’s the difference between building a business that serves you versus one that owns you. You are the one who always says that the successful business owners aren’t always the ones with their nose to the grindstone who never look up for air. They’re the ones who are spending some time looking around and paying attention to what comes next.

If feeling stuck in that day-to-day grind, because you wouldn’t be the only one, not the first one, and not the last one, and you can’t seem to find time to think about where your business is headed, you don’t have to do this alone. Gwen walked us through a great exercise for self-reflection and for figuring this out.

Gwen is a great thought partner. She is a great thought partner for me and a lot of people. She is good at helping you to step back and see the bigger picture so that you can work smarter instead of harder. We have a handy-dandy and a fresh way to schedule an appointment directly with Gwen. You can go to EverydayEffectiveness.com/Clarity and book a short session so that you can get Gwen’s eyes into what’s going on, and maybe some examination of those open loops, and start creating the space you need to run your business instead of surviving it. We are here to develop the business you really want, not the business that makes you miserable.

 

Mentioned in This Episode

Anniversary Series

 

About Your Hosts

Gwen Bortner has spent four decades advising executives and entrepreneurs in 45+ industries. She helps women succeed in business without sacrificing happiness by identifying their true desires and aligning their business functions. She spots overlooked bottlenecks and crafts efficient plans toward sustainable success that center your values and priorities. Known for her unique approach to problem-solving and accountability through the G.E.A.R.S. framework, Gwen empowers clients to achieve their definition of success without sacrificing what matters most.

Tonya Kubo is a marketing strategist and community builder who helps entrepreneurs build thriving online communities. As co-host of The Business You Really Want and Chief Marketing and Operations Officer (CMOO) at Everyday Effectiveness, she keeps conversations on track and ensures complex business concepts are accessible to everyone. A master facilitator with 18+ years of experience in online community building, Tonya takes a people-first approach to marketing and centers the human experience in all she does.