Your Dreams must be bigger than your fear

3. November 2019 20:44 by Jay Grossman in   //  Tags: , ,   //   Comments (0)


Last year I was eating lunch at a local Asian restaurant, and I pulled out an awesome message in my fortune cookie. It said, “Your dream must be bigger that your fear.” 

This message hits home for me, and this fortune is still attached to my monitor as a reminder.

What is a dream and what is fear?

A dream can be defined as a cherished aspiration, ambition, or ideal. It's something big that you really aspire or hope to accomplish at some point in the future.

A good example of a dream is when Boston Red Sox pitcher Chris Sale fulfilled his dream by pitching in and winning the 2018 World Series. (Being a Sox fan, I was very happy to see this happen!)

Fear can be defined as an unpleasant emotion caused by the belief that someone or something is dangerous, likely to cause pain, or a threat.

An example could be that I have fear that many folks will not like my blog and troll me tirelessly, causing much public shame.

So why don't people go after their dreams?

I have met lots of folks who have big ambitions or aspirations, but are content to follow a path that is more comfortable.

Jordan Jones of the Huffington Post wrote an article with her 9 Reasons You Won’t Pursue Your Dreams

  1. Because there is an easier, safer path.
  2. Because we’re waiting for the right time.
  3. Because we don’t have enough time.
  4. Because we didn’t succeed at first.
  5. Because we are too young.
  6. Because that’s not what I’m supposed to do.
  7. Because there’s already something else out there.
  8. Because all you have is an idea.
  9. Because you trusted a lot of crappy advice over your own instincts.

So how to counter your fear?

Steve Harvey is an interesting guy who has had a pretty amazing career. He was homeless (living out of his car) in the 1980's as he would figure out how to make a run of his dream headlining stand up comedy. He'd go on to host "Showtime at the Apollo" and I am sure he saw lots of folks try to go after their dreams. 

I LOVE this video from when Steve being interviewed by Oprah! They give insightful advice to an audience member:

  1. The way to counter fear with the size of your dream. You have to want something so big that the size of your dream overcomes your fear.
  2. Start where you are and you have to know your gift (and capabilities).
  3. You have to be clear about your vision.
  4. if you want to go after our dream, you need to surround yourself with other dreamers (people that go after their dreams). He says, "Stop telling your big dreams to small minded people".


I recently read a recent post by Ian Callum (Director of Design at Jaguar Cars) called Lessons learnt from 40 years as a designer. I liked this sentiment:

"Success is not something that will land in your lap. You have to fight for it, break past your comfort zone and put yourself in situations that can be scary."

My fear story
I have generally been more curious than cautious over the years, especially when it comes to opportunities. Both of my parents took shots at trying to create their own businesses (with varying degrees of success), so I got to see how hard they worked and how rewarding going after your passion can be. Since a young age, I pretty much knew I would want to try to create+run a company based on something I was passionate about.
Way back in 1995, I was a junior in college and I found the internet for the first time. It was awesome! Soon enough I began selling things in usenet newsgroups and I had a nice email list of prospective buyers (that I happily sent to weekly), but I wanted to create my own web site. I had no background in this and no idea where to start. I asked around and none of my friends knew either. The whole thing was so foreign to me that it was scary.
Thinking back almost 25 years ago, it feels like the stone age compared to today. Netscape 1.0 had been released as a graphical browser (but Javascript didn’t really work). All the great resources we have today to learn things like google, youtube, code schools/bootcamps, courseware like Coursera, stackoverflow, and quora didn’t exist back then.
I had some obstacles I had to overcome (but I found my way):
obstacle remedy
I didn’t have a computer of my own I used the Rutgers campus computer lab whenever I could get free time
I had no idea how hosting worked and I didn’t have much money to pay for it  I was lucky a student worker in the lab referred me to a free service -
I had no idea how to code anything I drove to a local book store and read an intro to HTML book (taking lots of notes on how all the tags worked, but not actually buying the book)
I didn’t have a digital camera or scanner to have pictures of my items I bribed a student worker at the computer center to show me how to use the one he had access to

So what happened

  • If something is your DREAM, then you are likely motivated to go after it.
  • I defined a first goal that was S-M-A-R-T (simple, measurable, attainable, realistic, timely). 
  • I needed to identify the obstacles that made me scared or apprehensive.
  • I came up with ways to de-risk those obstacles.
  • My fear was lessened and I took action!

Once I got something (super ugly) working and people could contact me to buy things I had listed for sale, I realized the beginnings of my dream were possible and my fears subsided. I stayed on this path of teaching myself tech stuff, and by 2000 I had to skills to build my dream web site (

This first experience led me to go on to a fulfilling career building software projects and managing engineering teams build all sorts of cool things. 

Meet my friend Connie (a.k.a. the Corgi Queen)

My day job employer (Rent the Runway) launched a mentorship program in 2015, where managers would get paired with contributors they usually don't work with. I was paired with a very nice + talented User Experience designer named Connie Cheng. She LOVES corgis (and has one named Lucy) to the point of mild obsession. Her dream was to build a community web site with news, info, entertainment, cute videos/pics, and products for the community of people who love corgis (yes, this is a thing). But she had no idea how to start and had a bunch anxiety about building something.

I wanted to help since building my own projects have been so fulfilling. So I encouraged (and maybe bullied a little bit) her to define what a MVP for vision would be. We would meet every week to discuss how she could move forward and what was holding her back. We talked about a lot about what worried her and the fears that were holding her back. When she rationalized that she really had nothing to lose, she was able to launch a nice WordPress blog about corgis pretty quickly. 

Today she runs a successful (and profitable + bootstrapped) business revolving around It's been 3 years since she had quit her day job to run her independent projects full time. She has a built a compelling brand and has designed lots of products corgi owners seem to enjoy. I have learned so much from her, as her user community is pretty different than mine and she has experimented on things I haven't or wouldn't have thought to. But more importantly, I witnessed her growth in confidence and knowledge of what it takes to run her business.

Paying it forward - Building a Passion Project class

Connie and I created a class called "Building a Passion Project" in 2017, that we run together as part of RTR EDU (Rent the Runway's internal education curriculum). Here is the marketing spiel:

Has something ever bothered you that you wish existed and no one has solved it? Do you wish that something worked or worked differently? How about sharing/interacting with folks with your obsessions? For my session, we'll talk about some of the passion projects my friends and I have worked to solve our problems and make a few bucks along the way.

We have run 5 sessions that have had probably a total of 150 or so students. The sessions detail:

  • some of our experiences around following our dreams
  • how to overcome your fears and get started
  • workshopping attendees through building something to following their passions

We have an active slack channel open to folks who take the class (and some of our ambitious/curious friends). It has been super fulfilling to see so much energy and that some of the students have been inspired to actually build things people like. 

About the author

Jay Grossman

techie / entrepreneur that enjoys:
 1) my kids + awesome wife
 2) building software projects/products
 3) digging for gold in data sets
 4) my various day jobs
 5) rooting for my Boston sports teams:
    New England PatriotsBoston Red SoxBoston CelticsBoston Bruins

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