Since we do not succeed in fleeing it, let us therefore try to look the truth in the face. Let us try to assume our fundamental ambiguity. It is in the knowledge of the genuine conditions of our life that we must draw our strength to live and our reason for acting.

— Simone de Beauvoir, The Ethics of Ambiguity⁷⁸

THERE'S A TRAIL system I love to hike outside of Kalispell, Montana. It's not a big draw like Glacier National Park is. If you're just visiting, you'd never even know that it's there. The trail system is unassuming, located in a small county park. But the terrain is exactly what I love about being outdoors in Montana—quiet, dry, and full of tamaracks. Plus, I can “choose my own adventure” with the trails to create exactly the hike I'm looking for. The only issue is that my mother-in-law told me to be wary of mountain lions a couple of years ago, and I'm still not over that.

The trailhead overlooks a small equestrian center, and the trail itself skirts its edges to start. Down the trail a couple hundred yards, right where the grassy field gives way to the woods, I confront my first choice. I can stay low on the Family Trail, or I can start making my way to the view on the Notch Trail. I choose the Notch Trail—a winding single-track with a moderate elevation gain. The trail leads me up to a few hundred feet from the overlook—at which point, I have a couple of options. Stay on the Notch Trail, or go left or right on the Overlook Trail. I always choose the one that feels like it will not have a black bear or mountain lion waiting for me. So far, I've never been wrong.

The south-side overlook gives me a clear view of the city of Kalispell and, beyond it, Flathead Lake. The north-side overlook gives me a view of Foys Lake and the Whitefish Range of the Rockies. Once I'm done at the top, I have new options. I can go back the way I came, of course, but I prefer to change it up. So I go back by way of the Plum Creek Road Trail. It's actually a logging road, and the trail is wide, less technical than the Notch Trail. From the Plum Creek Road Trail, I take the Family Trail to the Direct Trail back to the trailhead. Round-trip is about four miles.

The reason I wanted to share my favorite “daily hike” trail system with you is because it illustrates an important point: There is rarely a direct path to your vision. Instead, you go from trail to trail as you make your way toward what you want for yourself and your work. That much might seem obvious, but what is likely less clear is that there are a multitude of ways you can traverse those trails and still end up where you want to be. For instance, I don't have to start on the Notch Trail. I could start on the Direct Trail or on Plum Creek Road Trail. I could follow the trail system extension after I hit the overlook and keep climbing before I start downhill. It all depends on my mood, the experience I'm after, who I'm with, even weather conditions or whether I remembered to bring bear spray.

When I'm hiking, my desire is pretty clear and, therefore, so are my choices. It's not hard to know whether I should choose the more difficult trail or add on a few more miles at the top. What I care about is evident to me in that moment. My ability to act on my desires might be constrained by time or weather but even that is clarity I can use to make choices in the moment. The wider world offers much less clarity and far more choices. What we care about is also unclear—or at the least, what we care about is full of contradictions. As I've deconstructed the moral systems we operate in—rugged individualism, Protestant work ethic, supremacy culture, and so on—you might have noticed how these moral systems promote a course of action that might not line up with your personal values or vision. Yet, you know that conforming to these systems makes life easier and more comfortable in many ways. Given those contradictions, what's the right choice? When you're at one of life's trail crossings, how do you choose which way to go?

In all the confusion, we tend to get so fixated on how to make the right choice that we fail to make any choice. When we don't choose, we end up spreading our resources across many different courses of action. We end up overcommitting our resources and undercommitting to our responsibilities or projects. We learn little about what we do actually care about or need in a given situation and what action might be an effective way to get it. To avoid the spiral into overcommitment, you need a strategy.

Simply put, a strategy is your designated focus for a period of time. When you have set a strategy, you choose what to let go of—not forever, just for now. Your strategy is a decision about which way you'll take to get from one trail crossing to the next—not how you'll get to where you ultimately want to be. Setting a strategy simplifies what you care about and clarifies what's valuable to you for a given period of time.

For practical reasons, you might realize that your current job or family situation might require a strong work ethic in a way that necessitates a compromise on your personal values. Not in a way that is ethically strained but as a matter of utility. For instance, you might have a boatload of student debt. That debt burden leads you to set a strategy of paying off that debt with a side hustle, which is a drain on your time resources. Is it ideal? No. I believe higher education is a public good that shouldn't result in life-changing debt. But that's not the world we live in. You decide that paying off that debt is more important to you than the personal value you have for adventure that would lead you to, say, solo hiking the Pacific Crest Trail (PCT) with no source of income for six months.

It's not an ethical or moral compromise to delay hiking the PCT. You recognize that the delay serves the purpose of meeting an obligation you have to your credit history because of the system you live in. You recognize that the obligation (in this case, student debt) is a construct of the system, but commit to meeting that obligation sooner rather than later so that more doors are open to you later on.

What I love about strategy is that it dramatically clarifies objectives and lowers the stakes. Yes, the strategy you choose is important but it's not make or break. If you focus on a particular strategy for a year, you've not thrown away the potential to set other strategies in the future. So while you're fiercely committed to the strategy you choose, you can also relax. Fiercely committed and relaxed? That sounds good to me. Instead of anxiously wondering if you'll ever be able to hike the PCT, you know that the action you take now will make it possible.

While commitments give you a framework for growth through daily action, your strategy sets your direction. To go back to the hiking metaphor, my commitment is essentially putting one foot in front of the other. My strategy is the choice of trail and the outcome it leads me to. How do I choose? Well, I need a map. If I just set out on a trail without having an idea where it goes, I might eventually get where I was hoping to go, but I'm likely to end up miles away.

Make Your Map

Consider where you're at now and the personal vision you hope to create for yourself. What are some of the different experiences and projects that are going to come up along the way? These experiences and projects are like trailer markers; they help you determine the different options you have as you plot your course. When I make my map, I tend to work backward. I find that constructing the journey in reverse gives me a way to ensure that I work toward my end goal.

But before we go any further, we need to focus in. You can apply strategy and map-making to any area of your vision but I don't recommend making a map that incorporates your entire vision. It will be full of far too many assumptions and missing information. So the first bit of strategy work we do is to choose a particular area to work on. For many, this will be work or family; for others, it might be finances or advocacy. What area you choose only matters in that it determines what you'll see concrete progress on first. To that end, if there is a particular area that you need to create change in order to get healthy or feel more stable, choose that one. If a more sustainable financial situation, or career change, or political engagement would lead to the conditions that make other changes more manageable, start there.

I'll share an example to give you a feel for this process. A few years ago, my husband and I decided to start a podcast production agency after we spotted an opportunity in the market. We knew we could build on my own success in podcasting and bring a new level of production and content strategy for podcasts to business owners. We also knew that we wanted to build a company that we could eventually exit. Our shared personal vision is that our work revolves around our intellectual and creative pursuits, rather than working for or with others. So that was the ultimate destination to which we wanted to make a map.

Working backward, we considered what would need to be in place to sell a company. There are two key things: a strong book of clients and a proven, profitable system. Fulfilling those two requirements would be the penultimate trail crossing, so we could step back and consider what we might need to do to put those things in place. We'd need strong documentation and efficient processes as well as a pricing framework that paid all labor plus profit. We'd also need a staff that could produce podcasts without our direct management so that we could develop a large enough client base to make the business attractive to a buyer. Because a strong system and profitable pricing makes it much easier to staff up and increase capacity, we knew the next step down the trail was hiring and training. (Remember, we're mapping this out backward.) That meant our strategic development needed to start with building the system and finding the right pricing. With that decision made, we could break that strategy down into projects.

Setting strategy is like that old adage about eating an elephant one bite at a time. When you consider your personal vision overall, it's easy to be overwhelmed by the idea of everything you want to do or change. You freeze up and don't do anything; or, you try out a bunch of small experiments that don't lead to meaningful results. Your strategy focuses on a particular direction you want to see progress in and helps you create a plan for compounding growth. Here's how the process unfolds:

• Choose an area of your personal vision you want to work on.
• Identify the change you want to make or outcome you want to create. This doesn't have to be super specific, just identifiable and meaningful.
• Consider what you'll need to do immediately before you realize that change or outcome. There may be multiple pieces to put in place.
• Take a step back and consider what you'll need to do immediately before that.
• Repeat the process of stepping back and recording what all needs to be in place to create the piece you just identified until you reach something that feels like your current reality.

Once you've mapped out those different points, you connect them with trails. Think of this more like a flowchart than a linear path. What are all the different places you could start? Once you complete that trail, what are your options? Again, repeat the process until you have a map of the different paths you could take to create your vision.

The last question (for now) is: Where do you want to start?

Be gentle with yourself. Maybe it seems like there are no good options. Or maybe it seems like they're all good options, and you'd hate to miss out on any of them. Remember, strategy doesn't deny you opportunities. Strategy allows you to order your progress and focus on one thing at a time. Again, if there's a place to start that will provide for more stability or well-being, start there. If you're in a good place already, it's up to you and what you're most curious about.

Once you've decided which way you'll take at the trailhead, you might discover that your map needs some adjustments. As you move along, you gather new information and come upon other options that aren't on your map. Unlike a map for hiking, your trail map can always be adjusted as you learn and grow. So don't hesitate to update it as you make progress.

To finish off your map, name the first trail you'll embark on—that's your strategic priority. Your strategic priority is the jumping off point that helps you identify the projects you'll choose to work on, as well as the projects you'll put on the back burner. While your commitments help you choose the best course of action on a daily basis, your strategic priorities help you identify the longer-term investments you want to make in your growth and change.

Consider the trail you've chosen to embark on first and then reflect on what habits, routines, or systems need to adjust as you travel toward the next trail junction. Notice if there are any patterns that seem familiar or whether there's any overlap with another trail on your map. For instance, maybe your first trail is to prioritize your own needs. You notice that you have a habit of making sure everyone else is taken care of first—and you do this at home, at work, and even at the grocery store. At this point, you might not even know what your needs are (that's certainly something I struggle with). So you might decide that your first strategic priority is going to be to identify your needs and meet them. Just like with your commitments, your strategic priorities will be fairly broad. We're setting a course—not setting goals. We'll make it more actionable when we consider the projects you'll tackle to make it happen.

Wanting to Change Is Only the First Step

Imagine what six months or a year spent focused identifying your needs and meeting them would do for you. Imagine the other changes that might catalyze. Think about how you would feel different at the end of that period and the habits you'd learn to take with you as you continue on your journey. Of course, if it were as simple as just setting off down a trail, you'd have already done it by now. Change is hard—for so many reasons. Remember psychologist Robert Kegan who formulated the constructive developmental theory of psychology? Well, Kegan, along with Lisa Lahey, also studied why change is so difficult. Together, they created the immunity to change framework. What they discovered is that the reason it's so hard to make a change you genuinely want to make is that beneath that desire for change there's a competing commitment. There is something else that we're more committed to than the change we want to make.⁷⁹

Not long ago, I needed to change my work in a big way due to my health. While the course of action was crystal clear, I couldn't proceed for months because I had a competing commitment. I was committed to the appearance of success, like I didn't struggle at all. The idea of taking action that defied that carefully constructed public version of me brought me to my knees. My desire to appear invincible made me sicker than I already was. It took some difficult conversations with my therapist to identify this competing commitment and actually make a change.

The process doesn't stop when you identify the competing commitment, though. The next step is to examine why that commitment exists and why it's so important to you. That's what Kegan and Lahey call the “big assumption.” For me, the big assumption was that people would think less of me and abandon me if I admitted my struggle. And for that reason, I didn't respect my own needs or pursue the strategic action that I needed to take. As I admitted this fear and talked it through with my therapist and the rest of my support team, I was able to replace that big assumption, ease the competing commitment, and take the needed action.

Kegan and Lahey explain, “Big assumptions reflect the very human manner in which we invent or shape a picture of the world and then take our inventions for reality.” They suggest a four-step process for unpacking a big assumption. First, notice your current behavior. How does the way you behave today reflect or reinforce the big assumption? Second, explore evidence that contradicts your big assumption. Confirmation bias is tough to overcome—if you want to continue believing your big assumption, you'll find plenty of examples of why it's true. So you have to go out looking for evidence to the contrary. What stories or experiences (your own or others') show how your big assumption is false? Third, trace the history of your big assumption. Big assumptions are a method of sense-making—albeit an imperfect one. We form these stories about The Way Things Are as an attempt to make sense of events or experiences. If you dig into the experiences that you were trying to make sense of as you formed those assumptions, you can identify how that assumption served you in the past—and why it's getting in the way now. Finally, Kegan and Lahey recommend testing the assumption. How could you behave counter to your big assumption to prove it false? Can you try out a low-stakes version of the bigger change you're looking to make as an experiment? Starting to rewrite your big assumption by playing outside its boundaries in a less risky way will give you confidence to follow-through on your commitment to bigger change. Be sure to take time to follow this step by processing the results of your experiment. What did you learn? How did it feel? What were the concrete outcomes? Processing the results gives you a way to integrate and make sense of the new information.

It's our immunity to change that makes it so important to pick a trail and stick to it. It might seem like you could tackle a few different trails at once (forget the physics of that for a moment). How difficult is it to identify and prioritize your needs, after all? Or how hard could it be to pursue a promotion? Or what kind of challenge is spending more time with your family? But inherent in the desire to change are all of your competing commitments. For instance, if you're more committed to making other people feel at ease than you are to prioritizing your own ease, you'll continue to ignore your own needs. If staying silent in meetings for fear of rejection is more important to you than getting noticed, you'll continue to miss out on promotions. If responding to work emails after hours is what you're really committed to, you'll miss out on quality time with your family. And of course, underneath each of these competing commitments are the assumptions you've used to make sense of past experiences. Maybe ignoring your own needs was a way to maintain the peace during your childhood. Maybe staying silent has been a way to avoid being shut down or called out by people who don't value your opinion. Maybe the fear of what happens if you miss an email or make a mistake gave you the impression that being a bit distracted at home was a good trade-off.

Limit the strategic priority you choose to pursue. Don't set out on a 10-mile hike while also learning to dance and composing a poem. Give yourself permission to take it slow and go deep with whatever you choose to pursue.

Pursuing a Strategy is Practice

In Chapter 4, I examine the role of practice in life and work. Strategy requires practice-orientation. While strategy should have a strong sense of direction and progress, it's also firmly rooted in daily choices and experiments. It takes time and patience to notice competing commitments, narrow your focus, and try something different. And anything that requires time and patience is profoundly countercultural in a society that values speed and efficiency. There's a deep recognition of your own agency embedded within the pursuit of a strategy. When you invest yourself in your choice of strategy, you choose to ignore all of the shoulds and supposed-tos that are thrust on you from the outside world—the marketing messages, the social hierarchies, the short-term benefits. At first, exercising your agency will be an active, conscious practice. If that seems daunting right now, I get it. I really do. But the thing about practice is that, over time, the practice weaves its way into your subconscious. It informs your choices and actions without your active intervention. Your strategy becomes a part of who you are and how you relate to the world. And so, major growth arrives without fanfare.

adrienne maree brown, who reminded us that we need not assume misery is required for satisfaction, is a major influence to me on strategic change and growth. brown advocates for what she calls “emergent strategy,” an organic practice of noticing, relating, and adapting in exceedingly uncertain circumstances. She writes, “Adapting allows you to know and name current needs and capacity, to be in relationship in real time, as opposed to any cycle of wishing and/or resenting what others do or don't give you.”⁸⁰ Adaptation is also practice. When we adapt, we exercise our agency. And that brings us back to strategy. While strategy requires focus and commitment, it is not inflexible. Strategy is adaptive. Adaptation is strategic. There is something to learn in every step on the path.