Conquer Your Fear of Rejection

6 min readMar 9, 2022

Aversion to rejection is natural but left unchecked, it can paralyze your career. Here’s a simple method for overcoming that fear.

Corrigan says we are motivated to play games and increase our score. By taking a gamified approach to rejection, you can tip the scales in your favor to overcome the fear you feel.

When I heard this advice, I knew Corrigan was onto something. At that point, I had been doing something like it for almost 18 months, and I had seen the powerful impact it was having on me.

My Experiments With Rejection

In December 2019, I tweeted about a new experiment I was trying.

I had moved to Lisbon two months before, and I decided to make a weekly standing reservation for two at my favorite restaurant. Each week, I was on the lookout for someone to invite. If I ended up not meeting an interesting new person, or if I was rejected by someone I had invited, I would just go to the reservation solo.

I had three goals:

  1. Getting outside my comfort zone by dancing with the possibility of rejection.
  2. Taking the initiative to start a conversation and friendship.
  3. Building a routine in my new home by setting time aside in my schedule for a nice evening each week.

At first, the idea of inviting a complete stranger to my dinner reservation was squarely outside my comfort zone. I was convinced I would be rejected each and every time, and I wasn’t sure I could stomach that.

So, I started the experiment with people I already knew. I was brand new to the city, but I had a handful of friends and acquaintances so I started with asking them. I was surprised that I was even feeling fear doing this!

I started to view new people I met as people I could potentially add to that growing list of friends and acquaintances. Since meeting a new person and taking the leap to ask them if they wanted to join me at my reservation was far outside my comfort zone, I developed this approach instead. I took the pressure off by asking myself, “Is this someone I would want to add to my growing list of ‘friendly’ people I could ask in the future?”

Don’t get caught up in the particulars of my experiment. I was new to Lisbon and wanted to expand my friendship circle. I could have just as easily been new to an industry and keen to meet industry experts or others new to the space who could lend a hand in helping me grow my network or expand my knowledge.

Maybe for you this “rejection inoculation” experiment looks like getting more comfortable with cold calls for sales, public speaking, taking people you would like to have on your podcast to coffee, raising capital for your startup, or applying for a different role at your company. The point here is not what you are being rejected for, it’s that you are seeking out rejection as a way to reduce your fear of it. Because it turns out if you can get comfortable with rejection in one area, you have a lot less fear around it in other areas!

Over time, I started to notice my little dinner experiment had three effects that changed the way I think about rejection across all areas of my life, including business.


Rather than thinking, “I shouldn’t feel this way” when I was rejected, I intentionally tried to be more empathetic towards myself. Feeling sad or disappointed when we are rejected is normal. I told myself that it’s OK to feel the way I do, given this circumstance. As a way to step back a bit I would ask myself, “What would I tell a child who was feeling this way?” Rather than telling myself something harsh like “Get over it” or minimizing that “It’s just a dinner reservation,” I would attend to my feelings and validate them as real and allowable. Whether I am being told “no” to a dinner reservation or hearing “no” from a dream client I’ve always wanted to work with, being rejected for something that matters hurts. Learning to pause and feel that emotion has helped me to encourage myself at the moment of rejection rather than beat myself up.


There were a lot of legitimate reasons that someone would say no to my dinner reservation invitation. Reasons ranged from their trying to save money by not eating out to saying the week I proposed didn’t work for his schedule. When I first began hearing “no,” I would shut down and not be present to hear the reason why.

Noticing this surprised me. Both budgets and scheduling are two easily fixable problems! It’s important to be curious when getting rejected in business as well. Maybe a big client you wish would switch over to your software is stuck in a contract with your competitor. Or the person they ended up hiring for your dream role, instead of you, went to a specialized training that you could sign-up for too.

Once we notice the stories we are telling ourselves about being rejected, we can start to get curious and problem solve. In my dinner reservation experiment, I ended up solving the budgeting problem by treating my friend to dinner, and we both came away energized after discussing a new direction she was taking in her career. And the scheduling conflict wasn’t an issue any longer because it was easy to invite my other friend on a week later that month that worked better for his schedule. Over time, I found that when the volume of fear around rejection is turned down because of intentional exposure, I become more present to hear the other person’s needs and seek ways to uncover solutions. Asking when the contract with the competitor ends or following up with the hiring manager for your dream role in a few months after finishing that training are great ways to turn what could have been a painful story into information to use to reach your goal.


Whether I received an enthusiastic, “Yes! I’d love to join you” or was told that someone wasn’t up for coming to my reservation, I took time to congratulate myself for taking a risk. It was another data point that showed me that I can handle rejection when it comes my way.

Remember, for Corrigan, his quota was the number of times he was told no. When he met his quota, it was only because he heard “no.” So, in his case, he went a step further than I did in my small dinner experiment!

How can you reframe your measure of success from the number of times you succeed at your business goals to the number of times you try to succeed at your business goals? If we can celebrate taking a risk and thus turn down our fear of failure, we may be on the path toward reaching our business goals even faster.

Rejecting Fear of Rejection

Although the pandemic caused repeated pauses and restarts to this experiment, I have managed to have over two dozen of these reservations to date. As I became more settled in my routine in Lisbon, my calendar had more things than it did when I first moved. Over time, I decided to move the reservations from one per week to every two weeks.

Remember that your own “rejection inoculation” experiment may start off one way and take some turns over time. The point is to see where you are feeling fear around being rejected and rather than run from it, go towards it.

Reflecting back, this experiment truly ignited a superpower that surprises me. I feel a lot less fear around putting myself in the way of a “no.” This has impacted how I approach new projects in our businesses and even the way I speak up about things I want or don’t want in my personal life. The fear of both hearing and saying “no” has far less weight than it did before. I know it’s not the end of the world when “no” enters the conversation, and I understand there are countless reasons someone chooses to say “no,” and many times these reasons have nothing at all to do with the person who is asking. I am now at the point of the experiment where I even feel confident inviting complete strangers, like I did on Twitter a few weeks ago!

This article originally appeared on February 24, 2022, here:




Jacqueline Jensen is a COO, former venture-backed startup founder, TEDx speaker, author, and Royal Society of Arts Fellow.