5 Uncomfortable but Healthy Questions Every Anxious Achiever Needs to Ask Themselves 🧠
Stop Sabotaging Your Success: The Questions That Could Completely Transform Your Life (8min Read)
TL;DR Summary:
Questions can transform your mindset instantly, helping anxious achievers reflect and grow.
Key life-changing questions to ask yourself:
Am I living to impress others or fulfill myself?
What would happen if I failed—and what if I succeeded?
Who am I outside of achieving?
Am I saying "yes" to things I secretly resent?
What might fall into place if I let go of control?
Take time to reflect—the answers may surprise you. Share your favorite question!
These Questions May Change Your Life
If you’re a long-time reader, you know I’m a collector of questions.
Questions have the mysterious power to change our feelings, thoughts, and beliefs in seconds.
Which is why a good question is worth its weight in gold.
A group of people that doesn’t ask themselves enough questions are my anxious achievers out there!
We’re too busy grinding or attacking the next task to stop and think about what we’re doing and why.
Which is great for massive action, but not for developing deep wisdom.
Wisdom is experience plus introspection.
Without that last piece, you’re just taking tons of actions and getting lots of experience but you’re not becoming more wise.
I fall into this trap so often, which is why I make it a priority to pause and ask myself questions like the ones we’re covering today!
Grab a journal and buckle up.
I challenge you to take a couple minutes outta your day to really answer these questions for yourself.
Question 1: Am I living my life to impress others, or to fulfill myself?
Had to put the heavy hitters first!
I’ve lived a lot of my life to impress others.
There, I said it, hopefully, it’s easier for you to say it now too.
It’s ok.
This belief and behavior kept us safe or got us attention, love, and affection when we were young.
It’s easy to do when you’re rewarded for external achievements but aren’t reminded that you’re good enough and loved just for BEING.
You don’t have to DO anything to be enough or worthy.
These are big realizations that I’ve seen anxious achiever after anxious achiever come to after working through a question like this one.
Some good follow-up questions after this one are:
Who is it you’re trying to impress specifically? Why?
Do I even know what it means to “fulfill myself” yet?
If I were to make decisions as if no one else would ever know what I decided, what would I do differently?
Alright, time for question 2.
Question 2: What would happen if I failed—and am I avoiding that fear more than pursuing my dreams?
The inverse of this one is just as powerful.
What would happen if I succeeded?
The fear of success plagues just as many, if not more people than the fear of failure.
Outlining exactly what would happen if you failed though is a great way to beat the unknown fear you let rot in the back of your mind.
It keeps you paralyzed until you shine a light on it.
For example, I’ve been a full-time entrepreneur for nearly 5 years now.
It’s exhilarating but also terrifying, there’s no one coming to save you.
However, I can tell you that outlining exactly what failure looks like has been extremely helpful!
If I were to fail completely, which I have, I know what the worst-case scenario looks like.
Let’s break it down.
Let’s pretend, I have $0 in my bank account, I get kicked outta my apartment, my companies have failed, can’t pay my bills, can’t buy food, etc.
These are some of the biggest fears I’ve got in relation to failing.
Now that they’re in the light, I can create a plan for each.
If I had to move back in with my parents, I could.
If I had to get a 9-5 job to get back on my feet, I could.
If I had to restart a company from 0, I could, and have.
Now, the fears that could have prevented me from even trying to pursue my dreams are laughable…
I constantly have to ask myself this question, because as you move up and pursue one set of dreams and fears, a new set emerges!
Question 3: Who am I when I’m not achieving or checking things off my to-do list?
Damn… What a question.
I pondered this one for so long when I first got asked it in therapy.
I had no idea, and if I’m being honest, I’m just now starting to understand who I am outside of achieving.
It’s been my identity for so long…
In my experience, this one requires more than just journaling about it.
You’ve gotta get out there and test things.
Test hobbies, volunteering, going to movies alone, sports, therapy, new friend groups, and anything else that will help you get a feel for what lights you up!
Learning, basketball, watching movies, riding Birds (electric scooters), playing Pokemon, reading fiction books, and creating content like this blog are all things that light me up.
I didn’t just land upon these things randomly, I tested them all out to see if I’d like them and if they were really “me.”
How do you feel when doing the things you’re testing? Does it feel like you’ve gotta achieve something? Are you trying to impress someone?
Pay close attention to these things as you’re testing!
Question 4: Am I saying ‘yes’ to things I secretly resent, just to avoid conflict or discomfort?
As a recovering people pleaser myself, this question struck a chord in me.
Is “yes” your go-to response to things? If others need help, advice, time or attention, do you give it to them without a second thought?
Do you then think about how you wish you didn’t have to do all these things for others?
If you just said, “yes” in your mind, you might be a people pleaser.
It’s alright, I’ve been there.
The concept of “no” can be scary to people whose entire lives have been to achieve and serve others to feel like they’re enough.
Saying no isn’t just a word, it’s a completely new identity and way of being.
It comes with more conflict, discomfort, and fear, but it also comes with more happiness, peace, and fulfillment!
A great follow-up question for this one is: What are you afraid would happen if you did say no?
Don’t stop at one fear, keep asking this question over and over until you get to the root.
For example, let’s pretend you said, “Other people won’t like me as much.”
Ask yourself again, if that happened, what are you afraid would happen.
Then you said, “They won’t want to be my friend anymore…”
Ask again, let’s pretend that happened, what you afraid would happen?
“I’d have no friends, and be alone.”
“If other people didn’t like you, they didn’t wanna be your friend anymore, and you were totally friendless and alone, what are you afraid would happen or what scares you about that?”
“It would prove I’m not good enough and unlovable.”
“What if you weren’t good enough and you were unlovable, what are you afraid would happen?”
You see how I’m digging? Don’t just stop at the surface-level answer, keep digging.
You’ll know once you’ve hit the bottom, you’ll feel it.
You’ll feel young and vulnerable. That’s how you know you found the Part of you that’s holding onto the beliefs like “I’m not good enough.” or “I’m unlovable.”
Oftentimes, it helps to have someone help you with this, like a coach or therapist.
So don’t feel like you’ve gotta do this one alone!
Question 5: If I stopped trying to control everything, what might actually fall into place?
When I started dating again last year, I tried to control everything about the process.
I remember getting on Hinge, and thinking about swiping like it was a business or something I could optimize.
I’d set goals around how many swipes and messages I sent.
I’d test opening lines, try to optimize my profile, etc.
I wrote out my non-negotiables, who I wanted to become to attract the kind of person that I am, and read all the books.
When I was out in public I’d plan out cold walkups, think about pickup lines I could use, etc.
I was trying to control everything about the process, and, surprise, surprise, it didn’t work.
Sure, I went on some dates, and got some numbers, but I wasn’t getting closer to what I was looking for.
The more I talked about this with my buddy Miles, the more I realized how much control I was trying to exert on the whole process.
Miles is one of the most free-spirited humans I know, so his feedback was invaluable, and one night at our office, he asked me a question nearly identical to this one.
I couldn’t answer at first because I truly didn’t know, I couldn’t see past my need to control things.
This question shifted my perspective instantly though, and the very next week, I decided to test this out.
I’d gotten fed up with Hinge and didn’t think it was productive, it was truly a dopamine pit and one of the sources of my controlling behaviors, so I decided it was time to let it go.
So, I stopped swiping, got the number of the last person I matched with so we could set up a date, and then deleted the app.
It felt so freeing to let go of control and I could feel myself putting out different energy.
I shifted from a mindset of, “I will make this happen through brute force.” to a mindset of: “We’ll see.”
This was a totally foreign concept to me as an anxious achiever, but it worked.
A week after deleting the app, and adopting this new perspective, I went on a date with that final Hinge match.
What was supposed to be an hour-long basketball date, turned into tacos, ice cream, a streetcar ride, a walk around the River Market…
We’ve been dating now for 4 months, and it’s the healthiest, happiest relationship I’ve ever been in.
The moment I’d been trying to force into existence came to me almost the second I let go of control and let it happen.
What might fall into place if you let go? What magic are you preventing from entering your life by trying to control everything?
There’s only one way to find out.
The Magic of Questions
I like doing these question blogs every so often.
Instead of just preaching to ya’ll about brain science, these blogs feel more engaging!
More like we’re chatting about these things together.
I hope you like them too, and I hope these questions help you like they’ve helped me.
What’s your favorite question? I would love to hear.
Comment on the blog in Substack or email me back.
I might feature your question in a future blog like this one!
And, as always, until next time… Live Heroically 🧠