One of the reasons I love the Dear Guyset episodes is because they remind me that nobody is figuring this out alone.

Every month, guys send in questions about dating, work, confidence, fitness, ambition, and everything in between. On the surface, the questions can seem completely unrelated.

One guy wants to know if he's ready for a relationship. Another is wondering how to get his boss to notice his work. Someone else is trying to start lifting, launch a side project, or simply figure out what they're supposed to be doing with their life.

But the more I thought about this month's questions, the more I realized they were all pointing toward the same thing.

Underneath every question was a search for certainty.

Guys want to know they're making the right choice before committing to someone. They want to know they're on the right career path before taking the next step. They want to know a side project will work before they invest time into it. They want to know they're doing the right exercises before walking into the gym.

The problem is that life rarely works that way.

Most of the things worth doing require you to move before you feel completely ready. That's what this month's Dear Guyset episode was really about.

The Search for Certainty

The first question asked whether it's normal to want a relationship while also feeling unsure if you're ready for one.

I think that's one of the most relatable feelings in modern dating.

A lot of people are waiting for a moment that never actually arrives. They think one day they'll wake up and suddenly know they're ready. They'll feel completely confident, completely certain, and completely prepared for everything that comes with being in a relationship.

What I've learned is that certainty usually isn't the thing that shows up first.

Interest shows up first. Curiosity shows up first. Connection shows up first.

The uncertainty tends to stay.

One of my favorite lines from the episode was:

"There's never gonna be something that says go and proceed."

I think that's true for relationships, but it's also true for almost everything else in life. There is rarely a flashing green light that tells you it's safe to move forward. More often, you're standing somewhere in the middle. You like someone. You're excited about the possibility of something more. You can see a future taking shape, but you don't know exactly where it leads.

That's uncomfortable, but it's also normal.

If you genuinely enjoy spending time with someone, respect them, and feel excited about building something together, there is only one way to find out where it goes. You have to try. Not halfway. Not while keeping one foot out the door. You have to give it a real chance and see what happens.

Even if it doesn't work out, you'll know you showed up honestly. That's a much better outcome than spending months wondering what could have been.

If this is something you're wrestling with right now, I also wrote more extensively about it in How Do You Know If You're Ready for a Relationship?

Why Nobody Feels As Prepared As They Look

Another question from the episode asked something I think almost every person in their twenties has wondered at some point:

"Is it normal to still have no idea what I'm doing?"

My answer was simple.

Absolutely.

I think one of the biggest misconceptions about adulthood is that everyone eventually figures everything out. When we're younger, we assume that older people have access to some kind of secret roadmap. Then we get older ourselves and realize most people are navigating uncertainty in real time.

The details change, but the feeling remains the same.

You start a new job and feel like you have no idea what you're doing. You move to a new city and feel like you have no idea what you're doing. You start dating someone new and feel like you have no idea what you're doing. You decide to build something of your own and suddenly feel like you're making everything up as you go.

That feeling isn't evidence that you're failing. In many cases, it's evidence that you're growing.

Growth almost always requires entering territory you've never been in before. If you've never done something before, you're not supposed to feel like an expert.

That's why I loved the question about starting to lift.

When I first started going to the gym, I felt completely out of place. I avoided entire sections of the gym because I assumed everyone else knew exactly what they were doing and I didn't. Looking back, I realize I was putting far more attention on myself than anyone else was.

The truth is that most people are focused on their own workout, their own goals, and their own insecurities.

As I said in the episode:

"Nobody is thinking about you more than they're thinking about themselves."

That realization applies far beyond the gym. Most of the things we avoid are things we think we'll be judged for. We don't apply for the job because we're afraid of looking inexperienced. We don't start the project because we're afraid of failing publicly. We don't approach someone we're interested in because we're afraid of rejection.

Meanwhile, everyone else is busy worrying about themselves.

If you're currently trying to build confidence in the gym, I'd also recommend reading The Internal Monologue of Lifting, where I talk more about overcoming that feeling of not belonging.

The Difference Between Knowing and Doing

A few of the questions in this month's episode highlighted another lesson I've learned over the past few years.

There is a massive difference between knowing what to do and actually doing it.

One listener asked what to do when their boss doesn't seem to notice their work.

This is something I think a lot of people struggle with, especially early in their careers. Most of us assume that if we work hard enough, the right people will automatically notice.

Sometimes they do.

A lot of times they don't.

One of the biggest lessons I've learned is that presenting your work is part of your job. That doesn't mean bragging. It doesn't mean sending constant updates or trying to make yourself the center of attention. It simply means communicating your value clearly enough that people understand the impact you're having.

As I said during the episode:

"It is on you to let them know what you're doing."

The people who advance the fastest aren't always the smartest or the most talented. Often they're the people who have learned how to communicate their contributions effectively.

That's one of the reasons I put together The Intern Survival Guide. Even though it was written for interns, a lot of the lessons apply to anyone trying to stand out at work, build trust, and create opportunities for themselves.

The same principle showed up again in another question about starting a side project while working full-time.

I remember feeling overwhelmed by this exact problem after college. I couldn't understand how people managed a full-time job, friendships, relationships, workouts, family obligations, hobbies, and side projects all at the same time.

It felt impossible.

The reality is that it can feel impossible sometimes.

But I also think the projects that survive are usually the ones we genuinely care about.

One of my favorite ideas from the episode was replacing the phrase "I don't have time" with "I don't care."

That's obviously not true in every situation. Everyone has real limitations on their time and energy. But it's a useful thought experiment because it forces you to be honest about what matters most.

When something is deeply important to you, you usually find a way to make progress, even if it's slow. You carve out an hour before work. You stay up a little later. You spend part of your weekend working on it. The schedule isn't always perfect, but the effort continues because the project matters enough to keep choosing it.

What I've Learned

When I look back at all five questions from this month's Dear Guyset episode, I don't really see five separate topics.

I see five different versions of the same challenge.

How do you move forward when you aren't completely sure?

How do you commit before certainty arrives?

How do you start before confidence shows up?

How do you take action when you'd rather wait until you have everything figured out?

The answer, at least from what I've learned so far, is that most of life gets figured out after you start.

You don't become confident and then take action.

You take action and become confident.

You don't become certain and then commit.

You commit and learn from the experience.

You don't figure everything out and then begin.

You begin, and that's how you figure things out.

Maybe that's the real lesson behind all of these questions.

Whether you're thinking about a relationship, a career move, a side project, or simply trying to build a better life, you're probably never going to feel completely ready.

But that doesn't mean you should wait.

Sometimes the next step isn't about certainty.

Sometimes it's about trusting yourself enough to take it anyway.

Frequently Asked Questions

How do you know if you're ready for a relationship?

Most people never feel completely ready. Instead of waiting for certainty, focus on whether you genuinely enjoy being with the person, trust them, respect them, and want to continue building something together. If those things are present, the only way to know where it can go is to give it a real chance.

Is it normal to not know what you're doing in your 20s?

Absolutely. Most people spend their twenties navigating career changes, relationships, new cities, friendships, and personal growth. Feeling uncertain doesn't mean you're behind. It usually means you're in a period of growth and transition.

How can I get my boss to notice my work?

Don't assume your work will always speak for itself. Share updates, communicate your progress, and explain the impact of what you're working on. Presenting your work professionally isn't bragging. It's an important part of building your career.

How do I bring up where a relationship is going?

Be honest about how you're feeling. Tell them you enjoy spending time together and are excited to continue getting to know them. Clear communication is usually better than spending weeks guessing what the other person is thinking.

How do I start lifting if I've never been to the gym before?

Start small and focus on consistency. Ask for help, use beginner resources, and don't worry about impressing anyone. Most people at the gym are focused on themselves, not judging you. The goal isn't to be perfect on day one. The goal is simply to start.

How do people build side projects while working full-time?

Most successful side projects are built in small pockets of time over a long period. The projects that survive are usually the ones people genuinely care about. When something matters enough, you'll often find ways to make progress even when your schedule feels full.