8. Weakness (OW)

Ottawa, Canada

Dear Jamie,

In the recent weeks of working on my startup, I discovered my kryptonite. Whenever I see it on my calendar for the next day, the whole world looks a little less bright. Every time I’ve attempted to do it, my body resists vehemently and I end up spending hours procrastinating. I honestly haven’t procrastinated this hard since high school, which makes me appreciate how I’ve had very little of tasks I deeply despise since then.

This newfound weakness of mine is sales. Specifically the process of talking to strangers to get them to try my product.

At this point I’ve tried a couple different tricks to make it better:

1. Reframe my perspective

Perhaps because the only sales calls I get are from Scam Likely, part of me views sales as a cold and calculated approach to make money. Salespeople have whole scripts for how to psychologically manipulate you into buying what they’re selling. So thinking about myself and sales together did not sound pleasant.

After writing out and questioning my beliefs about sales, I saw that it doesn’t have to be about manipulation. What I built is meant to help the people that I’m reaching out to. Talking to them is how I understand their problems and see how I can help. If what I’m selling doesn’t align with what they need, then I won’t sell them on it. I’m betting most salespeople have this perspective themselves, and they’re not all sociopaths scamming old people out of their retirement money.

2. Positive self talk

As much as I like to think that I’m open minded and have a growth mindset, I’ve come to recognize there are areas where I am not. Sales is one such area where I’ve caught myself thinking “this is just something that I suck at”.

I have now stuck some sticky notes to my monitor stand (actually a cardboard box) with affirmations on them. One reads “Sales is a skill and I can get better at it”. I have found this helpful to look at whenever I start getting into the fixed mindset to remind myself otherwise.

3. Break a hard task into smaller pieces

When I view sales as an amorphous blob of a task, it’s very daunting. But tackling each piece of it individually has been more achievable.

First I made lists of people to reach out to, finding their contact info online and compiling them into a spreadsheet. Once I got into the groove, this part did not feel dreadful at all, though admittedly I was extremely slow at it. Ivy said I should be able to make a list of 30–40 people and reach out to them in half a day. In an entire day I was only able to do the list part of it.

Then I made scripts for what to say via email, Instagram, and phone call. Since I didn’t yet know what worked best, I tried conducting it like a randomized study, contacting people with different variations of methods. Instagram sales/marketing has been a completely novel learning experience for me and that turned out to be fun to dive into. The tactics for such a seemingly simple app actually go very deep.

Finally I did the reach outs. At first even email and Instagram were painful. At this point it literally was just copy and pasting text I’d already written from one screen to another. It should’ve taken fifteen minutes to go through all my lists. Yet somehow all my time and energy disappeared into a vacuum whenever I started the process. I’d emerge out the other side a day later having only messaged a handful of people.

After a few days of going at it, email and Instagram got easier and faster. Less of me died after each reach out. Calling nonetheless did not change. Whenever I called someone and they didn’t pick up, I’d let out a sigh of relief, despite knowing that was counterproductive and a waste of my time.

In the end, all these techniques did help a bit, but I am still nowhere near being an actual salesperson.

You may remember that in university I wanted to be a “Fat I”. A T-shaped person is a generalist in a wide array of topics and a master in one (or a few). Meanwhile an I-shaped person is a jack of all trades, master of none. I used to ask “why can’t I become a Fat I, a master of all trades”?

I think that was a belief that worked well for me at that time. It’s what drove my curiosity across different topics and got me to start Learning Night. I yearned to learn more about everything and didn’t feel so strongly about any particular subject to specialize more in it.

That belief doesn’t serve me anymore and now I’m more like a traditional T-shape and that’s okay with me. I better understand the limits of my interests in certain topics and have ones I want to go deeper in. So I don’t expect myself to become best in class at sales, but something about my complete inability to do it still irks me.

Is it just my ego hurting from feeling incompetent? Is it that this weakness seems like one I should overcome?

Nathan Myhrvold (who I’d argue is the closest person to being a Fat I) said in a recent interview “I tend to not advocate [for perseverance]. There’s no point in beating your head against a wall. After you’ve given the wall a few good cracks, move over and find a softer spot on the wall!”

Similarly, the Strengths Finder philosophy suggests we should focus on what we’re good at and delegate what we’re not to someone else who is.

We aren’t meant to be good at everything, I agree with these sentiments. But some weaknesses we need to overcome ourselves for the betterment of our lives. This one doesn’t affect my daily life, but if I want to be a founder, it’s something that I either need to overcome or I need to find a co-founder that supplements me on that front.

In a conversation with Ivy, she said that she could be convinced to be that supplement, but first I needed to sell her myself on my product, or at least my belief in the future of it. As I thought about this, I realized I didn’t actually have belief in my own product.

It doesn’t yet live up to my own standards and I don’t fully believe still it solves the problems of my customers. Perhaps that was the root problem behind it all. Perhaps getting on a call with someone will be a breeze once I develop belief in what I’m pitching.

Let’s see if anything changes going forward.

Your friend in weakness and in strength,

Owen