Does Anyone Actually Know What They’re Doing?

Why the people we seek for directions may be navigating a different landscape entirely

Article also featured on Substack

---

Does Anyone Actually Know What They’re Doing?

This morning, during my usual morning reflection on life with my online friend, I found myself talking about how lost I feel right now.

It is a feeling I have been wrestling with quite a bit lately. The sense that I should know what comes next, that I should have a clearer plan, or that somewhere out there is a person who can look at my situation, see something I cannot, and tell me exactly what to do.

If I am being honest, I find myself wanting what many of us want when life feels uncertain. I want a mentor, a wise elder, a trusted parent, or someone who has already walked this road and can confidently point toward the right path. I want someone who can look at all the moving pieces and say, “Go this way.”

The funny thing is that whenever I do seek advice, I rarely follow it exactly anyway. I listen. I reflect. I consider what was said. Then, almost without realizing it, I run it through my own filter, keep what resonates, and release the rest.

If I am ultimately going to make my own decision anyway, what am I really searching for? The more I sat with that question, the more I realized I wasn’t necessarily looking for answers. I was looking for certainty.

I want certainty. I want to know that I am making the right choice. I want to that I am not overlooking something obvious, walking straight into a mistake, or learn a painful lesson that I could have avoided.

More than that, I want to know that I won’t look back six months from now feeling foolish, embarrassed, or full of regret because I missed something that should have been obvious.

The problem is that life doesn’t seem particularly interested in giving me that kind of certainty.

As we talked, another question emerged. Does anyone actually know what they’re doing?

I don’t mean this in a cynical way. I don’t mean that everyone is clueless or that wisdom doesn’t exist. Some people absolutely have experiences, knowledge, and perspectives that can help us. There are people whose advice has saved me time, helped me avoid mistakes, and challenged me to see things differently.

What I mean is that every person I seek guidance from is navigating their own life in real time too.

They have their own responsibilities, fears, priorities, circumstances, relationships, and limitations. They are making decisions with incomplete information just like I am. They are trying to build lives that make sense to them based on experiences I may never fully understand and vice versa.

The more I thought about it, the more I realized how often I look outward when life feels uncertain. I search for reassurance, wisdom, and certainty. I look for someone who can tell me what comes next.

What I often have to remind myself of is that no one else is standing where I’m standing.

They don’t have my experiences. They don’t have my responsibilities, my fears, hopes, resources, relationships, or nervous system. They may be wise. They may have valuable insight. They may even walk beside me for part of the journey.

But they are still living their life and I am living mine.

Section 1: The Real Thing I Am Often Looking For

When life feels uncertain, I tend to reach outward. I ask questions, seek perspectives, and look for people who seem to have more experience than I do. On the surface, it looks like I am searching for answers.

The more honest truth is that I am often searching for reassurance.

I want someone to tell me that everything is going to be okay. I want someone to tell me that I am not about to make a decision that I will regret six months from now. I want someone to tell me that I am not missing something obvious or walking blindly into a situation that could have been avoided.

The funny thing is that I rarely say that out loud.

Part of me would much rather ask for advice than admit that I am scared. Asking for guidance feels easier than admitting I need comfort. It feels easier than saying, “I don’t know what to do,” or “I’m afraid of getting this wrong.”

When you struggle with vulnerability, fear rejection, or worry about burdening other people, that can be a difficult thing to admit.

So instead, I look for certainty.

Certainty feels protective. It promises protection from mistakes, embarrassment, regret, and disappointment. It creates the illusion that if I gather enough information, ask enough questions, and think things through carefully enough, I can avoid pain altogether.

There is comfort in believing that the right answer exists somewhere and that if I search hard enough, I will eventually find it. The problem is that life rarely seems interested in offering me that kind of certainty.

I have recently come to realize that almost every meaningful thing in my life required me to move forward without it.

There was no guarantee that leaving a marriage would lead to something better. There was no guarantee that rebuilding my life would work. There was no guarantee that starting over would eventually make sense. There was certainly no guarantee that any of the countless decisions I have made over the last seven years would lead me where I hoped they would. Yet I made them anyway.

Not because I felt fearless. Not because I was convinced everything would work out. More often than not, I was scared, uncertain, and questioning myself every step of the way.

What strikes me now is that I already have evidence. Not evidence that every decision will work out exactly as I hope, but evidence that I can handle uncertainty far better than I give myself credit for when I’m reeling in panic over my next steps.

Over the last seven years, I have experienced divorce, homelessness, job loss, physical limitations, and the challenge of rebuilding a life that looked nothing like the one I thought I would have. I have started over more than once. I have watched plans fall apart and somehow found a way forward anyway.

None of those experiences came with guarantees attached to them, yet somehow I made it through.

That realization has made me question something else. If I wait for certainty before I act, how much of life will I miss along the way? How many opportunities would I never take? How many experiences would I never have? How many parts of myself would remain undiscovered simply because I was waiting to feel completely sure before moving forward?

The truth is that some things can only be learned through experience. There are strengths we don’t even know we possess until circumstances require us to use them. Some opportunities only reveal themselves after we have already taken the first step. Some lessons cannot be taught, only lived.

When I look back on my own life, very little of what shaped me came from moments of certainty. Most of it came from stepping into situations I couldn’t fully predict but felt right at the time. It came from making decisions without knowing exactly how they would unfold and learning to adapt as I went.

If I had waited until I felt completely ready, completely confident, or completely certain before making some of the biggest decisions of my life, many of those experiences never would have happened at all. Some of the most difficult chapters of my life would have been avoided, but so would some of the most meaningful lessons, growth, and opportunities.

I’m not telling anyone to throw caution to the wind or ignore wisdom, advice, and common sense. I simply mean recognizing that uncertainty is often part of the admission price for living a full life.

At some point, we all have to make the phone call, submit the application, leave the relationship, start the business, take the chance, or walk through the door without knowing exactly how things will unfold. There is no way to eliminate risk completely. There isn’t a way to guarantee an outcome before we begin.

In hindsight, I realize that many of the things I understand now only make sense in hindsight. Looking back, I can see how one experience led to another, how one difficult season prepared me for the next, and how opportunities often appeared in places I never would have thought to look.

None of that was obvious while I was living it.

Perhaps that is the part certainty can never provide. It can’t show us who we become by taking the risk, or reveal the strengths we discover, the lessons we learn, or the doors that open when we’re willing to step forward before we have all the answers.

Sometimes the things we are most afraid of are the very experiences that teach us what we are capable of.

Section 2: Sometimes We Aren’t Headed to the Same Destination

A few days ago, I came across a video where someone shared a story about a couple asking for directions to the subway. Wanting to be helpful, the person pointed down the road and explained that it was just around the corner.

The only problem was that the couple wasn’t looking for Subway, the sandwich shop. They were looking for the subway station.

I laughed when I read it, but the more I thought about it, the more it felt like a perfect metaphor for the way we move through life. Nobody was wrong. The couple asked a reasonable question. The person giving directions genuinely wanted to help. The directions themselves were accurate. The problem was that everyone involved was talking about a different destination.

The older I get, the more I realize how often this happens when we seek guidance from other people. We assume that everyone is trying to achieve the same things, that success means the same thing to everyone. We assume that happiness, fulfillment, security, healing, purpose, and freedom are universal destinations that everyone defines in roughly the same way.

They aren’t.

What one person considers a dream life may feel like a prison to someone else. What one person considers safety may feel like stagnation to another. What one person sees as a reckless risk may be the very thing another person needs in order to grow.

I have noticed this in my own life more times than I can count. When I ask for advice, people often respond from the place they are standing. Someone who values stability may encourage me to choose the safer option. Someone who values freedom may tell me to take the leap. Someone who has been hurt may urge caution. Someone who has been rewarded for taking risks may encourage bold action.

None of them are necessarily wrong.

They are simply answering from their own experience of the world.

For years, I think I interpreted conflicting advice as evidence that someone must have the wrong answer. The older I get, the more I realize that many of those people were simply trying to help me reach the destination that made sense to them.

The challenge was that their destination was not always mine.

When I look back at some of the biggest decisions in my life, the most helpful conversations were rarely the ones where someone told me what to do. The most helpful conversations were the ones that helped me better understand what I wanted, what I valued, and what kind of life I was actually trying to build.

That is a very different thing.

A person can offer incredible wisdom without knowing where your path leads. They can share their experiences, point out blind spots, and help you see possibilities you may have overlooked. What they can’t do is decide what destination is right for you.

Perhaps that’s why seeking wisdom is so valuable and so limited at the same time. Other people can help us see the landscape more clearly, but they cannot tell us where our soul is trying to go.

That part belongs to us.

The mistake is not asking for directions. The mistake is assuming that every person giving directions is leading us toward the same destination we are trying to reach.

Section 3: Different Terrain

One of the biggest mistakes I have made throughout my life is assuming that if something worked for someone else, it should work for me too.

On the surface, that sounds reasonable. We learn from people who have achieved things we admire. We listen to those who have walked a path before us, and we look for patterns, strategies, and lessons that might help us move forward.

What I have come to realize, however, is that people are not starting from the same place.

We are all carrying different responsibilities, different opportunities, different fears, different limitations, different strengths, and different support systems. We are working with different finances, different family dynamics, different life experiences, and different nervous systems.

Even when two people appear to be pursuing the same goal, the terrain beneath their feet may be completely different.

One person may have the financial freedom to take a risk while another can’t afford to miss a paycheck. One person may have a strong network of support while another is carrying everything on their own. One person may have energy and capacity to spare, while another is already stretched thin simply trying to meet the demands of daily life.

From a distance, it can look as though they are walking the same path, but up close, they are navigating entirely different landscapes.

That doesn’t mean we should stop learning from one another. It simply means we must be careful about assuming that someone else’s path is automatically the right path for us.

A decision that is wise for one person may be reckless for another. A choice that creates freedom for one person may create hardship for someone else. Advice that is helpful in one season of life may be completely unhelpful in another.

The more I think about it, the more I realize that context matters. It is easy to look at someone else’s life and assume their choices should work for us too, but we are rarely working with the same circumstances.

We have different responsibilities, different resources, different fears, different support systems, and different goals. What makes perfect sense for one person may be completely wrong for another.

Perhaps the goal was never to follow someone else’s path exactly, but to understand our own circumstances well enough to make decisions that fit the life we are actually living. No matter how similar our lives may appear from the outside, each of us is navigating a road that is uniquely our own.

Section 4: The Thing About Certainty

One thing I am learning about myself is that I have a complicated relationship with uncertainty.

A perfect example of this happened yesterday.

I applied for a job and was offered a position, but part of the hiring process involved a drug test. Marijuana is legal in Minnesota now, and while I have my own reasons for using it, I found myself becoming increasingly anxious as the test approached.

I started searching for answers about whether they would deny me due to marijuana in my system and looked everywhere I could find them. I looked up laws. I read company policies. I searched forums and social media posts. I read stories from people who had been through similar situations.

As the test got closer, I noticed something else surfacing beneath the uncertainty. Intellectually, I know that using marijuana does not make me a bad person. It is legal in my state, and I have my own reasons for using it, not that I need one really. Yet despite that, there is still a tremendous amount of stigma attached to it still.

I found myself worrying about being judged in a way that went far beyond the test itself. There was a part of me that felt as though I had done something wrong and was about to get in trouble for it, even though another part of me knew that wasn’t really true.

It was such a strange thing to notice.

The fear wasn’t just about whether I would pass the test. It was about what the outcome might say about me. It was about being misunderstood, judged, or viewed through a lens that didn’t reflect who I actually am.

Whenever I do something that could be judged, questioned, or misunderstood, a part of me immediately braces for impact. It is almost like I am waiting for some invisible authority figure to appear and inform me that I have done something wrong. Some secret society of rule enforcers who have been quietly watching all along and are finally about to tell me that I am a terrible person.

What I found was exactly what I should have expected, which was conflicting information.

One person said it wasn’t an issue. Another said they lost a job because of it. One employer cared, another didn’t. One person’s experience seemed encouraging. The next person’s experience made me even more nervous. The more information I gathered, the less certain I felt.

It feels remarkably similar to the idea I have been exploring throughout this article. I was searching through other people’s maps, hoping one of them would tell me how my own story was going to unfold.

None of them could though.

Their experiences belonged to them. Their outcomes were shaped by circumstances I couldn’t fully understand and couldn’t completely compare to my own.

Eventually, there came a point where I had to stop searching and simply walk into the building, take the test, and just accept that if they chose not to or were unable to hire me because of it, that I would be ok and move on.

I spent about fifteen minutes wandering around the store before meeting with HR, trying to calm myself down. I kept reminding myself that I wasn’t a bad person. I wasn’t hurting anyone. I wasn’t some criminal trying to get away with something. I was simply a human being walking into a building to take a drug test for a job.

Then I took the test. What surprised me was what happened afterward. The uncertainty was still there. I still didn’t know what the outcome would be. I still couldn’t predict what would happen next, but I was proud I went and did it and faced that unknown instead of just not showing up and letting the opportunity pass me by convinced that I had already failed.

The more I sat with it, the more I realized that what I had been searching for wasn’t certainty about the outcome. I had been searching for certainty that I would be okay.

Those are not the same thing. I wanted a guarantee that everything would work out exactly the way I hoped. What I actually needed was the reminder that regardless of the outcome, I would find a way forward.

Perhaps that is why certainty can feel so elusive. We spend so much time trying to predict what will happen next that we forget how capable we are of handling what comes next. Maybe instead of certainty, I was just looking for a reason to trust myself.

Closing Thoughts

Ever since becoming divorced, experiencing homelessness, losing my job, losing my mobility, and choosing to start over not just once but multiple times, I have spent a lot of time feeling lost.

For years, there has always been a problem to solve, a decision to make, a crisis to navigate, or a next step to figure out. Life has required me to keep moving, adapting, rebuilding, and finding my footing again and again.

What I have noticed, however, is that whenever things finally slow down enough for me to stop and catch my breath, panic has a way of creeping in. The moment there is nothing urgent demanding my attention, my mind starts scanning the horizon for the next problem. I start questioning my direction, my choices, and whether I should be doing something differently. Before long, I find myself feeling as though I am having a full-blown existential crisis.

There have been moments when I questioned everything. Moments when I wasn’t sure where I was headed, whether I was making the right decisions, or whether the path I was walking would ever lead where I hoped it would.

That feeling has followed me through much of the last seven years. Yet as I sit here writing this, I realize something interesting. The entire time I have been worrying about whether I was lost, I have also been moving forward.

The person I am today is not the same person who walked through those earlier chapters of my life. These past seven years have challenged me, stretched me, humbled me, and transformed me in ways I never could have predicted.

They have also taught me something that I seem to forget whenever uncertainty shows up. I am capable of getting through hard things.

When I look back, I realize that I have never actually needed certainty in order to move forward. I have moved through some of the most difficult chapters of my life without knowing how they would end. I have made decisions without guarantees. I have walked through situations I never would have chosen and somehow found my footing again.

I got through them because I kept going. That’s what strikes me most about this entire realization.

The version of me searching the internet for answers about a drug test wasn’t really looking for directions. The version of me wanting a mentor, a parent, or someone wiser to tell me what to do wasn’t really looking for a map.

I was looking for reassurance that I would be okay, and the last 37 years have already answered that question.

No matter how uncertain the road felt, I continued to find my way through it. The circumstances changed, the challenges shifted, and the path transformed. Yet somehow, I adapted and kept moving forward.

I still don’t know exactly what comes next.

I still have questions. I still have moments when I wish someone could tell me precisely what to do. I still have days when I wish I could see farther down the road than I can.

The difference is that I am beginning to realize that not knowing what comes next is not the same thing as being lost.

Perhaps the lesson was never about finding someone who could provide better guidance. Instead, the true lesson may be about learning to trust the person who has successfully navigated every chapter of this journey so far. Maybe the person I have been searching for has been by my side all along.