On Navigating Precarious Positions in Entrepreneurship

I found myself navigating mountain roads in snow and ice this morning—the kind of icy road with a seductive layer of fluff masking an ice-coated pavement underneath. Add curves and drop-offs with a minuscule margin for error, and you have a recipe for tension and danger. I felt like everyone was heading away from the storm, and I was heading straight for it. It wasn’t a position I particularly wanted to be in, but here we were. I was driving between safety and peril in this fragile limbic space. It felt precarious. My body was tense. My shoulders scrunched toward my ears, my hands gripping the wheel, and my eyes narrowed. My breath was held and shallow.

When we are in precarious situations, our response reveals our rehearsals. Our level of training shows. I’m thankful. My training has taught me to breathe. To soften the muscles around my eyes. Soften my grip. My training has taught me to work well with myself and tell myself the things I need to hear when it counts. Things like, “Easy now. Easy. You’re ok. Go steady.” Not unlike what I might tell a horse right on the brink of panic.

As I softened my body and relaxed my breath, it wasn’t that I softened because the danger was past. I softened and regulated my breath BECAUSE of the danger – because adding tension to an already precarious position will amplify the risk.

I didn’t want to be “bold” or “exponential.” At that moment, I wanted to be ok. And I could choose to BE ok right now despite the tenuous roads.

This kind of dance between safety and risk is not so different than learning to navigate precarious moments in the life of an entrepreneur. Entrepreneur means “bearer of risk.” So, when you are in business for yourself, it’s not IF you encounter a position you’d rather not be in. It’s WHEN. And how you respond in that moment matters. Your response has the power to enable you to navigate danger well or completely lose your shit and make it much worse.

If you are reading this and are in a season of plenty: save this message to come back to in those times.

But if you are going into the winter of your business a little leaner than you’d like, lean IN with me.

For simplicity, just for today, I’m going to address revenue or lead leanness. It’s a common one but can be full of shame. Most entrepreneurs want to keep it extremely secret that they are struggling in these areas. Especially if they have been in business for a while and worry what people might think or feel as if they are “supposed to be passed this part.”

Going into the “winter” and holidays leaner than you’d like, there can be added pressure. Families are getting together. Those get-togethers inevitably lead to conversations about “how you’re doing” or “how your business is going.” Regardless of what you choose to disclose, on the inside, it’s hard for those conversations not to leave you feeling a bit battered and insecure about where you are and what you’re doing.

This time of year also leads to a cultural buzz around goal setting and knowing exactly where you are going. While there are process and tools to help, sometimes you are in a different kind of season-- especially as you mature as an entrepreneur. These seasons of "fog" mean that you only can see the next step ahead and really can't answer fully exactly how your year -- or next chapter of contribution-- will really unfold. You'll have to tune out the noise especially over the holidays.

Another holiday pressure is the traditions around giving. Especially if you’re generous by nature. The desire to take care of—and maybe even be wildly generous with your loved ones- might be a part of what got you into being in business for yourself to begin with. So, it can feel extra tough to know how to participate from a place of abundance when you don’t feel very abundant at this very moment.

The holidays have a rhythm of their own. This time of year likely feels different than how you usually operate. You eat differently, sleep differently and conduct your time differently. Those aren’t bad things, but if you aren’t aware of the dynamic, they can contribute to an overall feeling of being “off” or ill at ease if you are already feeling tender about your current position.

Then, there’s the pressure to fix the situation. Being in the red is not a place you want to be. You don’t want to be going through this. And you can feel the pressure to do ANYTHING to escape the pressure immediately. DON’T. Not yet. Give yourself a little credit. Of course your goal isn't to stay in this position permanently, just like my personal goal isn't to eternally drive treacherous road conditions. But responding isn’t the same as panic-reacting.

This moment can be a disaster of suffering or the greatest gift. Challenge and opportunity are two sides of the same coin. So, the quality of your response matters.

Most of the time, though, when I see a panic reaction with clients, it’s in the eyes. It’s in the voice. It’s in the body, like jerking on the wheel or slamming on the brakes on an icy road.

Their instinctual solution is to double down on all efforts or work harder, to go longer hours, to create proposals and programs that they don’t even want to deliver. To discount their prices so far down that they secretly hope for a no even though they feel as if they need the yes.

These are the actions of flailing. Gripping the wheel too hard. Holding the breath. Thinly veiled panic and the acrid smell of desperation. This kind of reaction will take you in the OPPOSITE direction you want to go. Give it a few months, and your panic-react might even lead you to burnout, exhausted doubt, and a self-fulfilling prophecy that you “tried” but should quit.

If that’s you, remember the icy road driving strategies. Admit the danger– you can even yell it. Be wide awake to its knife edge. (That’s focus for free, by the way). AND soften the grip. Take a breath. Widen the aperture of your focus. Talk to yourself well. Choose to be OK right now at this moment.

Does that response solve it all? Of course not, but it addresses the initial panic flailing. Once you aren’t gripped for all your worth, slow down so you can see what’s happening and what is truly here for you.

The other tendency I’ve seen that is equally common is to “go blind” to the danger. I call that “going floppy.”

To pretend that it’s fine, take the holidays completely off (not in an intentional abundant recovery way, but in a “head in the sand” and hope and pray it will magically fix itself by January kind of way. It’s like the fear response of “playing dead” (or playing pretend while going on a spree).

As an entrepreneur, this reaction doesn’t work. Period. More to the point, this particular tendency leads to the kinds of overindulging that worsen the situation and extend the lesson in the long run.

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Here are some practical ways my clients have navigated lean holidays (but not stayed there for long):

Participate in a way that contributes to true well-being. Don’t overgive beyond your means to prove how well you are doing.

Have boundaries. You can be truthful without being a tell-all TO all. Don’t discuss the intimate details of your challenges with people who don’t need to know. Be ok.

Go quiet—but don’t go dark. Don’t go numb and limp. Watch your patterns when you feel pressure. Learn your tendencies better so that you can weave this into your strategy moving forward.

Of course, if you have some simple short-term opportunities now, do it. (Relaxing does wonders for helping you spot opportunities you couldn’t see when gripped).

Run your own race. Be VERY intentional about keeping your eyes on your lane and not compare.

Lean into your chosen support systems.

Have the upward stream look. Get ready for January, look at February. Clarify some solid, simple ground you can stand on that will increase the likelihood of opportunities and flow coming to you soon.

And above all, remember. Energy speaks volumes. So whatever you choose, do it with a sense of awake ease. Ease isn’t a mindset; it’s a way of organizing the body. So, you can choose to be at ease even in the thick of things. ESPECIALLY in the thick of things. It doesn’t mean denying the risk. It means softening and staying present BECAUSE of it.

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You will find yourself in a lean season sometime (be that revenue, leads, time, or emotional bandwidth). We all do. (Yes, there are ways to significantly reduce the frequency and duration of lean times. That’s a part of what I do with entrepreneurs and a different topic).

I’ve been in business for myself now for ten years. I’ve had many moments of plenty and many moments where, for various reasons, I was leaner than I’d like to be. I’ve also supported many clients over the years in their entrepreneurial journeys and the inevitable moments of “the dip” that comes with the growth trajectory.

When I work with someone, I intend that they are prosperous in all ways. It’s my deeper intention that they learn to permanently embody the skills, strategy, traits, and habits that create prosperity AND that their peace and well-being aren’t dependent on it.

Overall, yes, it is good to be honest with yourself. You don’t want to traverse treacherous conditions and lean times as a permanent state.

Learning to be equanimous, awake, and navigate risk with grace ARE capacities you can build, however. They might be some of the most translatable capabilities you can ever develop. They support you to be able to “go out” when everyone else is “hunkering down.” They allow you true bandwidth to take in life richly even when you are on a challenging bit of trail.

I can’t think of anything more deeply empowering than to quietly know on the inside that you know what to do to be well regardless of the conditions around you.