Episode 105: How To Stop Checking Boxes And Start Living Life

In today’s episode, I examine how When-Then thinking is keeping us stuck. How it is preventing us from accepting ourselves, living in the moment, and seeking solutions from within.

I didn’t want to experience life–I wanted to master it.

I was too caught up in my goals to enjoy what was right in front of me. I figured that when I checked all the boxes on my goal list, then I would finally be happy:

  • WHEN I have a life partner THEN this experience will be awesome

  • WHEN I am thinner THEN I will be happier

  • WHEN I am less busy THEN life will be more peaceful

  • WHEN I am more present THEN I will be content

And because I wasn’t present in the moment, not living in the moment was holding me back  

We live our lives in When Then statements. We spend too much of our time waiting, hoping, wishing for our broken selves to be fixed so THEN we can be happy. 

What if you aren’t doing anything wrong? What if happiness isn’t something you attain permanently? What if you are thinking about it wrong?

All this month we are looking at how self-help isn’t doing us any favors and is leading us astray, particularly those of us with High Functioning Anxiety who love looking outside of ourselves for the answers.

In today’s episode, I examine how When-Then thinking is keeping us stuck. How it is preventing us from accepting ourselves, living in the moment, and seeking solutions from within.

Listen to the full episode to find out:

  • How to start accepting ourselves as we are so we can start living the moment

  • How we can have happiness without devaluing the daily experience

  • 3 Myths of When-Then thinking

  • And recognizing life’s daily opportunities so we can experience life more deeply and fully

Research and resources mentioned:

+ Read the Transcript

"This is so much fun," my said friend said to me as we walked through the Local Arts Fair on an early summer day. The place was buzzing, and it was fun to be out and about. I smiled and nodded. It was a beautiful day, but all I could think was WHEN I have a life partner, THEN this would be awesome.

I spent most of my 20s and 30s living that phrase. No matter what I was doing, it was always WHEN I have a life partner THIS will be better.

I also had other WHEN-THEN's. WHEN I am thinner, more accomplished, less busy, more present, in better shape, THEN I will be happy, peaceful, content, etc. WHEN I get THERE, then I will be happy. But the When I find a partner THEn everything will be better was my catch-all. A life partner was going to be my saving grace. Every problem I had got lumped into not having a life partner.

We live our lives in When Then statements. We spend too much of our time waiting, hoping, wishing for our broken selves to be fixed so THEN we can be happy.

What if you aren't doing anything wrong? What if happiness isn't something you attain permanently? What if you are thinking about it wrong?

"You're listening to The Happier Approach—the show that pulls back the curtain on the need to succeed, hustle, and achieve at the price of our inner peace and relationships. I'm your host, Nancy Jane Smith."

All this month, we have been talking about the ways the self-help industry keeps those of us with HFA stuck. When-Then thinking is one of the most toxic. The challenge with When Then is that it keeps you from accepting yourself, it keeps you from living in the moment, and most importantly, it keeps you chasing something outside of yourself. People with HFA don't trust themselves. I mean, why would they? Most people with HFA believe most of their personality needs to be fixed. So the When-Then combo is an easy one for them to follow.

It doesn't have to be something as specific as my when I find a life partner. It could be when I get better organized when I have a regular meditation practice when I stop people-pleasing or procrastinating.

When-Then thinking is a trap. AND it is a favorite phrase for those of us with HFA. At our core, we believe we are broken, so part of our identity is the need to improve.

We also love checklists. Tell me what I need to DO to improve, and I will do it. That is the attitude I had for much of my adult life. But then I realized it isn't about WHEN or SOMEDAY it is about who I am now. I have to be kind to this person I am right now not when I check everything off the list or BECOME my dream person.

If you think about it, it is less about who you want to become and more about not liking who you are now. People with HFA are in perpetual motion. So when I say to my clients, what if you are already there? What if this person is who you will be forever? They always look at me disappointed. This is why in episode 101, we talked about Radical Acceptance. Radical Acceptance is key to breaking up with When Then syndrome.

But something else is missing. It is more than just radical acceptance. We need to change the goal.

Sonja Lyubomirsky, psychologist and researcher in the field of happiness and positive psychology suggests that we put too much emphasis on our initial experience. So we believe the when/then mentality and WHEN we are happy, then everything will be blissful and greatly. But happiness never lasts. On the flip side, we believe when something goes wrong, THEN we will be always miserable. So the first myth is the when/then. When I get married--when I have a baby then I will be happy. And the 2nd myth is if we are unhappy, it will last forever. If we get a divorce, make the wrong choice, etc THEN we will be miserable. We get wrapped up in that black and white thinking, clutching like mad to the idea of happiness at any cost.

What if the point isn't happy? What if the point isn't to be content? Or to find peace or anything positive at all?

What if the point of life is to experience it? Experience life and all it's messiness.

As I say that, my whole body exhales.

For too many years, I clutched tightly to the reins of life. I didn't want to experience life I wanted to master it. Winning, doing it right, shifting my attitudes, building my skills that was the goal. Beating my anxiety, conquering my Monger (aka inner critic) were the goals.

We get so caught up in the surface. We miss the depth of life. We concentrate on the happiness of a wedding and the bliss of a honeymoon. We miss the juicy underbelly of the depth that comes when you lean into your spouse and get curious rather than scream and yell at them. Or when the doctor says your spouse has a cancer diagnosis and you lean into him/her and say, "we got this." When you wake up tired and exhausted from minimal sleep due to a sick baby and your spouse hands you a warm cup of coffee, that is happiness. But we miss that because we are so caught up in permanent happiness.

I still default to grabbing the reins, I still default to telling myself when-then but now I know that is a myth. That thinking sends me down a spiral where I miss out on my life.

Now I am going to be honest, this way of living is a bit counter-cultural. Living your life based on experiencing as much as possible rather than chasing happiness goes against all most all the Instagram quotes, self-help advice, and personal growth memes out there, which instruct you HOW to live. Those of us with HFA don't need any more instruction. We are drawn to it like moth's to a flame, but it is counter to what helps.

You don't need more directions coming from outside of yourself, you need to get to know what is going on inside of yourself. It starts with replacing the value of happiness with the value of experience. When you replace the value of happiness, you are no longer drawn to the myths that Sonja discussed. You won't make decisions based on if you will immediately feel happy or unhappy. Instead, you will make decisions based on the opportunity to experience life.

And as far as my life partner, yes I did find one. And he is amazing. AND he definitely isn't the answer to all my problems. He did not fix me. In fact, he brings all his problems issues to the table. If I had one wish it would be to go back to my younger self and say live your life. Partner no partner, it isn't better it is just different. Don't miss what you are doing, thinking that will fix you.

Rather than beating yourself up for never getting married, because happy people are married. You will recognize that life isn't a bunch of check-boxes, life is daily experiences, minute by minute of talking, seeing, soaking up life. There is no when then there is just now. And when we just when-then we miss the depth that comes from truly living. And that depth, isn't guaranteed happy, that depth includes sadness, exhaustion, joy, anger, peace, doubt, fear, bliss, contentment, in one big messy experience


It's no secret that I have a bone to pick with the self-help industry. The solutions it sells leave women living with hidden anxiety--women like you--with more stuff to be anxious about. Or worse, it turns you off from getting help completely.

I want to help you dial back the overwhelm and overthinking with a set of tools designed just for people like you. It's not woo-woo. It's not trying to positively think your challenges away. And I'm certainly not going to tell you to start living your best life.

I work one-on-one with women like you to deconstruct why anxiety creeps upon you and give you something to do about it.

Here's how it works:

First, we meet for an extended 90-minute session to uncover your stories and habits. You know, the ones that keep you stuck.

Then, you continue to work with me on-demand through an app that lets you leave a message for me any time you start to feel anxious or whenever you feel the Monger attack. I'll get back to you with action steps for moving through the discomfort and finding peace. Plus, you'll continue to meet with me for monthly sessions, too.

Working with me this way is an incredibly efficient and effective way to deal with your anxiety in the moment--without waiting for your next appointment.

One of my clients said: "It is extremely powerful to have professional advice and wisdom every single day. Being able to get support in real-time on anything you are worrying about or having panic attacks about or things that you struggle with daily has led me to managing my anxiety much better and helped me see what works best for me when I try to manage it. I found that it is just as—if not more—effective as one-on-one sessions."


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Episode 106: The Benefits Of High Functioning Anxiety Are Destroying You

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Episode 104: Self-Loyalty Starts With Better Self-Care