What to Do When You Feel Stuck in a Cycle of Uncertainty

I walked out of the building and into my fear of the unknown.

I was unsure of where or what I wanted to do next, but I felt, for the first time in a long time, at ease. However odd; it was true. I was now unemployed without a secure job. However, I felt calm and at peace.

The Fear of the Unknown

I tell you this to say; I have been there. I understand the cycle. I understand the need for more. The desire to make an impact. The desire to find meaning in what you do.

It is tough. Maybe the hardest thing we will ever have to do.

Which is why I believe that we all continue doing work we do not like doing to keep on living, which is to keep on doing work we do not like. It is a vicious cycle that is fueled by our fear of uncertainty. I had broken the spell twice, after quitting two jobs, but it kept coming back.

I thought that if I could just find my dream job, I would finally overcome my anxiety. I would overcome my insatiable need for more. I would finally be happy. I thought wrong.

After deciding that a new job in tech sales (“Dream Job” #3) would only mildly decrease my anxiety and longing for impact, I declined the opportunity and vowed to focus solely on the possibilities that would bring me freedom and purpose.

However, I found myself this week in the exact same situation as I had been in 3 times before. With the same fear, confusion, and desire to be “somebody.”

“The moment that you feel that, just possibly, you’re walking down the street naked, exposing too much of your heart and your mind and what exists on the inside, showing too much of yourself. That’s the moment you may be starting to get it right.” – Neil Gaiman

A firm offered me an excellent opportunity to be one of the first hires of a VC-backed startup. A dream job. Excellent salary, equity, and the chance to put my name on something. The opportunity to build and create. These were what I thought were the main components of a dream job, so I should be ecstatic to take them. However, for some reason, it did not feel right.

As a means to discover what was going on ( because I was unable to detach myself as I mentioned above) I ask myself, why do I want this job?

Here are the reasons that I came up with:

1. Salary and Equity

2. Founders with amazing backgrounds and networks that I could leverage in the future

3. Opportunity to build a start-up from the ground up

4. Responsibility to own and run a team

5. Title: Director of Operations. At 25? Awesome.

6. Easier story to tell at cocktail parties. Instead of saying, “I run a blog that helps people with anxiety;” I could say “I am the director of operations for a VC-backed startup in SF.”

7. It would be a good story to tell future B-Schools

8. I would have the opportunity to travel to China

9. Increased status amongst peer group

These all look like pretty reasonable reasons to take a job or pursue an opportunity. However, as I look deeper, I found a trend to my past career decisions. The stink of status anxiety is everywhere. I could build a startup with Harvard grads. How cool is that? I would be the director of operations with a team under me. Oh, how important. I would have equity in a VC-backed company. I can see the future mansion and ponies now.

However, for some reason, I became aware of something missing. Too thick to put a name on it. A slight sense that maybe this was not the path I was meant to take. However, even that thought has self-defeating follow-ups: Do you not want the job because it is hard work? You are so lazy. Are you just worried you would be anxious under pressure? I thought you solved this, Ben. Are you just making this job out to be bad to satisfy your self-fulfilling prophecy?

The reality of the matter is that this situation did not feel right. I could not figure out why, exactly, but something inside of me knew. As a person who struggles with anxiety, this is not something new. For awhile, even the most mundane tasks would require a pro and con list to determine if it was the correct move or not. To check myself and ensure that this was a real problem and not just masked anxiety, I decided to ask myself a simple question.

What is the most important result I want for my life right now and how can I optimize for it?

The first (and most vital) step on the journey toward a happy and fulfilled life is to define what result you want most and then optimize your life, accordingly. Then, once you have established your result (although it can change), move forward without a care in the world what anyone else thinks about it. Knowing that to get the result you want, you will have to give up others.

For example, if you want to be rich, there is a pretty defined path to get there. Show up to everything. Meet as many people as you can. Work harder than everyone else. Moreover, so on. However, you will have to give up some freedom. Not all freedom, but you will not have the complete control over your days. However, that is okay because being rich is what you are after.

On the other hand, if your desire is to have freedom. You can optimize your life in a way that gets you that, too. You will not become as rich as those who optimized their life for wealth, but you will be able to do what you want when you want, and with whom you want (the W’s). You can still be financially abundant, but you will not be the richest. However, that is okay because freedom is what you are after.

If you can define a single result or intention that you want to optimize your life for, then all of your decisions become easier.

The lie that I was telling myself was that if I optimized my life to be rich now then one day in the future, I could just transition my life to be optimized for freedom once I had all the money in the world. Moreover, this could be true, but if freedom was the end goal all along, why wait? Why defer it? Why kill yourself working 80 hour weeks to get something that is obtainable today?

In the past, I had no idea what I was optimizing my life for. I was just kinda going with the flow with a generalized desire to be happy and rich. Following the path of all those who have gone before me. However, thanks to up-close and ongoing exposure to anxiety, I am forced to think about these types of things on a semi-consistent basis. Oh, the joy. Moreover, the conclusion that I came to is that I wanted to control my W’s. I wanted creative freedom.

The next question then is, would taking the job optimize my desire to have creative freedom and surround me with an intimate group of people I loved?

The answer is simple. No. It would not. I would be working 80-hours a week building someone else’s dream, away from my fiancé and friends.

However, for whatever reason, the shiny new object diverted my attention and there I was, doubting myself again…

Stop being lazy, Ben. This job will offer you a great salary and the potential for a balloon payment in a couple of years. Suck it up and deal with it. Everyone else is. You should too. Besides, you are building a startup. There are thousands of people who would pay for the opportunity you are being given. Just be grateful and take it.”

Logical. Practical. Reasonable. Even though it failed to match up with what I wanted to optimize my life for, I still couldn’t shake the insatiable need to have a higher status in the world.

Enter superpower.

My anxiety. My superpower. My north star. Started to perk up and ask some questions about my logic…

Anxiety: Would taking this job optimize my desire to have creative freedom with an intimate group of believers?

Ben: No.

Anxiety: Okay, then you know what you should do.

Ben: But, am I just being lazy?

Anxiety: Ben, lazy people, don’t ask that question.

Ben: Yeah, but…

Anxiety: Stop. Be true to you. It is the only way.

Ben: Okay.

…Oh, how I love conversations with my inner self!

Moreover, so I did what I felt inside was the right thing to do. I declined the position and stepped into the unknown.

I still fear failure. I still get anxious about my status in the world. However, for the first time in my life, I am no longer living a life that is comfortable or easier to appease the masses. True, it may be harder to find a job in 6-months (if I fail) than it would be now. True, I could find part-time work and float myself for longer. True, most people in my “network” probably view me as less successful now. That is okay. I like it better this way. I like the smaller circles. The smaller circles are where the magic happens.

Ask yourself this question…

What do I most want to optimize my life for?
Answer with a single word. Only one. Use that word as your north star. View every decision through the lens of your word. Stick with it no matter how absurd or crazy it may look, feel, or seem. Doing this is what has helped me make some of the biggest decisions of my life, which almost all of them seemed completely absurd at the time. However, as Steve Jobs job famously said, “you can only connect the dots looking backward.” It will all make sense later. If you follow that fierceness within you, you cannot go wrong.

There are no dress rehearsals. Believe in yourself. I believe in you.

Benjamin Foley
Benjamin Foley

Founder, Fully Rich Life

Benjamin is the founder of Fully Rich Life, an online business that is focused on helping people decrease stress and anxiety, naturally. Join thousands of readers in his free 21 Day Mindfulness Challenge.

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