The Questions

January 30, 2026

It’s seven questions I’ve asked myself when my life stopped working the way it used to.

I recommend you ask yourself these questions, someday. I think of them in my head while driving, they hit me when taking showers, when I’m waking up in the morning or going to sleep at night. Use them however you like…I wish you the best and most fruitful of lives. Service starts now:

Why am I still doing this?

This was in reference to smoking…and this was a TERRIBLE question to ask myself. I had to admit that there wasn’t a reason, and then I had to quit. It was awful.

But, on the other side of that, I feel better, I have more money, and I am much happier. What’s your cigarettes? What this question really is “What used to serve you, but now confines you?” Where are you playing it safe, and resting in a habit that long ago stopped serving you?

Did I ever love her?

Love hurts. Vulnerability hurts, and is scary. We all desire closeness but fear losing control. The idea of being seen is one of our deepest desires, the only thing more powerful for most people than that is the fear of being seen and then rejected.

Saint or sinner, model of chastity and purity or party boy/girl, we all have regrets, mistakes, and failures.

The trick, in my opinion, is to get to the end with as much experience and as little bitterness as you can. I have no answers for how to do that…I think figuring that out is what life is.

Am I broken, beyond repair, hopeless?

I am deeply convinced that everyone should go to a therapist at least once in their lives. It’s so easy to feel like anything wrong in your life is a personal curse. But, here’s the thing, and why therapists can sometimes seems almost psychic. They see the same shit over and over. We all feel inadequate. No one is ready. We all have regrets.

I will leave the best thing I’ve ever heard on this subject right here, from Allain de Botton:

A deeply heretical set of thoughts rears its head: perhaps you deserve to be here. Perhaps you are not inherently shameful. Perhaps you are allowed love and, every now and then, to be loved in return. Perhaps you can be at ease with who you are, with what you want and with all the mistakes and embarrassments you have (like all of us) generated. Perhaps no one would complain if you took a few baby steps to freedom.

Should I be nicer to myself?

This is unique in the question pantheon: I didn’t intentionally ask this of myself. It popped in my head, unprovoked, while I was shopping for something plain and pedestrian, like yogurt or milk. A fleeting, transitory thought. I have come to believe that there is a lot of wisdom in our fleeting thoughts, if we just take a moment and listen.

What’s really bothering me?

When I’m off, angsty, upset, there is often something that will present itself as the source of that upset. When you’re in a bad mood, you can always find a reason why. But the first thing I latch onto is rarely the true cause of my discontent. Sometimes I’m unhappy because I feel like life could have been different, I somehow could have done better, and I’m not where I feel I should be.

Sometimes I’m tired. Sometimes I’m hurt that I have to explain myself to people, and feel they should understand me more.

Sometimes reconciling how you feel about your body as you get older with what you remember being younger to be like…well…that’s rough.

Sometimes you haven’t talked to someone in a deep and intimate way in too long.

Sometimes you’re getting sick and you haven’t realized it yet.

So take a deep breath, and ask yourself with me, “What’s really bothering me?”

Why don’t I feel like doing this?

There’s always a reason you’re putting things off.

Do you hate doing it, and only do it when you whip yourself into action? That’s a recipe for disaster.

Do you not know what to do? And, when I say this, I mean the literal next step. Take out the book, open the word doc, lace up your shoes for the run, grab your work out bag. What is the next physical action you need to take? If you can name it, doing it will often lead to the next and then then next. A thing begun is half done. Avoidance is often ignorance masquerading as procrastination. This also helps slice through big, amorphous tasks. It’s impossible to check off ‘get in shape’ from your todo list, but you sure as hell can check off ‘drive to gym.’

Do you fear the scope and/or intensity of the task? Hard to start working on your backlog of emails when you have 100. If it’s 10,000 it’s a nightmare, and you can’t realistically do a million without some serious self-hatred. We often see the scope, and fear the entirety, so we avoid the problem and make it worse. Not rational, but very human.

Trick 1: name what being done will look like, (and stick there). If you have 10,000 emails, say you’re only going to spend 30 minutes on them today. Then do 30 tomorrow, and 30 the next day. Adjust up over time if needed (depending on your in-flow) but I do know that 30 minutes is infinitely better than 0. And small changes do lead to big things over time.

Trick 2: Tasks expand to the time allotted. Try to do things faster. Get in, get out.

Trick 3: The courage to be rubbish. Can you allow yourself to write less polished emails until you have dug out of that mess. Or is there something else you can let slide until the backlog is solved. The trick in life is often that you can do anything, but you absolutely cannot do everything.

Trick 4: Decide it isn’t a problem. Hey, the 10,000 emails didn’t really bother you up to now. All failures besides death are mental anyways.

Why am I doing all of this?

I’m really sorry to end with this question, because I haven’t answered this question yet. I have some inklings, some trailheads of answers, and interests and obsessions. But I don’t know what ties it all together. I am happy that I’m asking the question, and couldn’t imagine life differently, but I just don’t know.

If you have that answer for your life: super jealous. I’m going to keep exploring. If you want to listen to me try and figure it out, I run a podcast called Serves You Right, and I have episodes that come out every Tuesday and Thursday. Listen anywhere fine podcasts get served. Cheers!

PS All the Questions in one spot and a link to the show: Why am I still doing this?