Dream-killing stories and how to vanquish them.

Written by caroline.caselli Published in

When I tell people I quit my job to start my own tech company (as a former social worker, with no experience building software), I get a range of reactions: they’re incredulous, they ask about my finances, and they ask whether I am terrified on a daily basis.

Fear was my go-to reason for not leaving social work. So what changed? 

An opportunity, and a pointed question. That was all it took. Three years after coming up with a way to streamline the affordable housing application process, I had innumerable product sketches, wireframes, accelerator applications, informational interviews, and funding leads, but I still didn’t have a product.

It could have continued that way, but my life coach finally asked me the right question, at the right time. A local healthcare startup offered me a management position that would pay me substantially more than social work. I was tempted to accept, even though it would mean putting my company on hold another year. My life coach knew that I was terrified of really trying to make Haven Connect work and that I doubted that my skills would be sufficient. She asked me, “When are your dreams going to be enough for you?”

Her question hit home for me. There wasn’t a need for more information: I simply had to take the leap and really give it a shot. The day after I resigned, I knew it was the right decision. Failure wouldn’t be as bad as missing the opportunity. And now a year later, I have a product and the beginnings of a business. 

So, what prevents you from doing what you love?

Here are 5 common fearful thoughts that can come up:


I’m not [insert your fear here] enough.

Ah, the fear of never enough or not good enough. The anxiety of feeling that you or your skills aren’t adequate to the task at hand can be crippling. Especially in the Bay Area, where it seems every 22-year-old is the next wonder kid. Or where Steve Jobs’ legacy of obsessive perfectionism is considered the sine qua non of product design. But if your sense of inadequacy prevents you from taking the first step, you will never get closer to making that dream a reality. So slob it down and ship it. Even a first draft is better than a blank slate. 

I want to be better.

This is sort of a subcategory of “not enough,” but masked in forward momentum. There is a sense that if only you were better or faster or stronger (cue Kanye), then your side-hustle would be accelerating faster. Obviously, this isn’t just a desire for growth, but a subtle form of insecurity that can stop you from taking the first step until you’re at the level you think you need to be. Don’t let perfection get in the way of progress. 

I don’t have the personality for leadership.

This is the fear that “I am not a real leader and don’t know how to lead people.” The good news is that leadership is learnable. Thank goodness. Otherwise, the first year of management would be the same as year two (a real bummer, both for you and your employees).

I don’t have the focus to complete this.

You know your Netflix procrastination isn’t doing you any favors, but trying seems scarier than binging on OITNB. The good news: willpower and focus can be cultivated. Telling yourself your attention issues prevent you from self-actualizing is just another negative story that can be changed. There are ways to structure your life to manage your energy and maximize flow, or “the mental state of operation in which a person performing an activity is fully immersed in a feeling of energized focus, full involvement, and enjoyment in the process of the activity.” If you want, you can trade in Piper Chapman for Mihály Csíkszentmihályi any day of the week. This, combined with managing your energy, can be a game changer. 

I’m not ready.

Take it from me - you’re never really ready. I prepped for 3 years (whoops) and still wasn’t ready to hire designers and developers, to build a client-centered application, or to figure out what mattered most to property managers. While some reservations indicate that you care enough about your dream to think through the obstacles, there is also wisdom in the Zen saying, “Leap and the net will appear.”



7 Strategies to deal with negative self-talk:

The good news is that thoughts aren’t facts. Thoughts are changeable. The stories you’ve told yourself for years don’t have to be the ones you listen to in the future. Here are some of my favorite ways of dealing with those anxious stories:


This self-care checklist is one of my favorite lists for overall well-being. Note the rating system, too. Sometimes it’s interesting to rate yourself, then focus on cultivating more self-care over the next few months, and then re-rate yourself to see whether anything changes. Sometimes prioritizing areas you’ve neglected is enough to bring transformation in old thoughts. Each experiment is a step closer to your desired future.  


Practicing meditation can help train your mind to be still. Sometimes just getting quiet can put things in perspective. Generally, it takes a few minutes for your mind to settle down enough to enjoy the silence. So, don’t sweat it if you’re reminded of your to-do list, your ex, or your critical need for cat food. Just wait it out. Just refocus on your breath every time you realize you are thinking about… well, anything that isn’t your breath. Feel the incremental way your stomach extends as you inhale, the way the temperature changes on your nostrils as you exhale, and the weight of your body. 

As you do so, you’ll start to get familiar with some of your negative self-talk. As you notice the patterns of negativity, you start to recognize the fallacies. You can start to call out the planning thought, or the judgmental thought, or the fearful thought. 

Your monkey brain isn’t unique to you. So, don’t beat yourself up when you notice the fear. The whole point is that you notice it and gently bring your attention back to your breath. It is a practice. As in, you have to practice to increase your capacity to rest in silence. 

It’s easiest if you start small—one minute. Just sit there with your eyes closed, using a timer (like this one) and if you sit there for the whole minute, you win! Pat yourself on the back, and move on with your life. You can build up from there. 

Or, if rolling solo doesn’t appeal, try a Mindfulness Based Stress Reduction Class. Or use one of the myriad of apps that provide guided meditations, like Headspace or Stop Breathe Think


So many options to choose from! Therapy is to your brain what the mechanic is for your car. Sometimes you just need a tuneup, and other times there is more work to be done. My favorites are cognitive behavioral therapy (CBT) and cognitive restructuring, with a heavy dose of mindfulness. It’s a little bit of a contradiction — CBT is about deliberative thinking, while cognitive restructuring and mindfulness is more about witnessing awareness. More on that here. Either way, talking to a professional can be an incredible way to be supported in the understanding of your personal stories. You can build trust with one other person, and start to understand your personal narrative more clearly. Having another person to explore and call you out on your negative thoughts can be the first step to stopping them. 

Support Groups

If you’re craving more group work (e.g. looking to have your experiences mirrored back to you, or just trying to connect with other folks going through the same stuff), there are a plethora of options for you. After you’ve thought about what you’re looking for, you can start the process of finding the one that is right for you. When those self-sabotaging stories see the light of day, other humans can either reassure you they simply aren’t true, or can empathize with similar stories. 


Writing down your own thoughts can be a surprisingly effective way of learning what you know. Over time, you’ll see patterns you have developed, perhaps a coping mechanism or two that is no longer useful. You can combat those negative thoughts you’ve written down, potentially just by asking what else is possible. For instance, if you wrote, “I’m paralyzed by fear,” you might counter by writing, “I am capable of managing my fear” on a post-it, so you can have a daily affirmation every time you look in the mirror (or open your closet, depending on how comfortable you are with posting your affirmations publicly). Another option is writing a gratitude list

Emotional Freedom Technique

If you’re down to try something a little silly in the name of getting rid of your emotional barriers, you can always experiment with the Emotional Freedom Technique (EFT for short). Basically, you’re trying to release trauma that has been stored in your body by tapping along certain points on the body while stating affirmations aloud. It’s like EMDR, but easier, since you can practice solo. 

Clearly it’s not a socially acceptable to be tapping your head while you’re on the subway, so it’s probably best to try this in the privacy of your home. 

Work Your Way Out (Literally)

Then again, if you’re a type-A overachiever, you can always try to work your way out of your emotional barriers, a la Mandy Stadtmiller (also one of my favorite inspirational ladies). Because really, you don’t need permission from anyone to go out and build the life you want to live. 

So track your self-care, go to therapy, meditate, check out a support group, practice EMF, and take the baby-steps to release yourself from the emotional baggage that subtly elbows you away from the life you want to live. You deserve it.

Or if all else fails, just put this video on repeat. 


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