Update: New Direction

Kassandra Zimmerman
Who Asked For Your Opinion
5 min readMay 14, 2023

It has been a while since I’ve posted an update. Whoopsies!

I’ve had a lot going on — just like everyone else in the world — and I’m still working on making this into a habit. I’m always on the struggle bus when heading to habit city.

My boyfriend and I broke up. I had an existential crisis of what my end goal is. I have far more plans than I’d like to and have had to drive every which way constantly.

SO, update. I got 2 more clients!!!

It’s crazy to me. They both came from Upwork with very little effort. I got emails from both of them requesting my proposal for their job listing.

I responded as soon as I saw the emails. I wrote my response highlighting why I thought I would be a great fit.

Here are some notes on what I wrote.

First New Client

The first request was for a custom font. I’ve made many custom fonts, so I let her know that and sent her some examples. I also sent her a link to a tool that she could possibly use to say save money and have it automatically generated herself (Calligraphr). However, through the course of our conversation, I found that her needs were broader in scope and also required a higher level of quality than Calligraphr can provide. Plus, one of the fonts she needed was a calligraphy font. While you can make a calligraphy/cursive font with Calligraphr and make the ends and beginnings meet, Calligraphr lacks a lot of the tools and guides that software like FontForge has to help speed up the process and optimize the font.

For instance, in FontForge, you can set up situational kerning and alternates and you can’t do that in Calligraphr. What does that mean?

For any who don’t know, when some letters end up next to each other they need a bit more or less space that the default amount or it will look unusual. That’s where the kerning applies.

The alternates, though, those come in handy at the beginning and end of words and following certain letters. So let’s say that you finish your words with a bit of a flourish. A ‘Y’ with a flourish at the end isn’t going to fit well in the middle of the word, but at the end it’s fine. Or let’s consider the letters that end high (b, o, v, w). These letters typically are written in such a way that they end at x-height (or up in the middle of the line of text instead of near the bottom where the letters all rest). So, we set up an alternate for every letter to make that atypical connection from up high instead of down low.

Anyhow, getting back to new clients, I talked to her organically. I tried to pair her with the best next steps. I discovered that she plans to sell the font and Canva templates using said font on Etsy. I have used Canva to make templates AND I have an Etsy shop selling digital downloads, so I was able to speak to both of those needs as well.

In the end, just talking casually and communicating what I prioritize in my process and work, that was enough to win her trust and the ability to fulfill the project.

Second New Client

The second one wasn’t related to the kind of work I’d like to be doing, but when you’re just starting, you have to be open to the opportunities, whatever they may be, to fill in the gaps to make ends meet.

The second request was just for taking some pictures of groceries for a store audit. It was fantastic work in terms of efficiency! I was able to make $45 per hour. I could meet the minimum threshold of products photographed in 3 hours instead of the 6 hours that they forecasted. I made just short of $470 going to a grocery store for 3 to 6 hours 3 days of one week.

I also built another connection that expressed a willingness to work with me more in the future.

Other Work / New Goals

So I mentioned early a bit of an existential crisis defining my end goal. A large part of my struggles these past couple of weeks has been around figuring out what I want to be doing.

This past year I was employed as a CSO (Chief Strategy Officer) for a startup. I got so much incredible feedback and felt the most validated and supported that I ever have in my life. It was incredible, and feeling empowered from that, I’ve had walls come down that were blocking me from feeling that I could pursue whatever I truly want.

I started considering acting, singing, and dancing. When I was younger, I loved singing and dancing. I wanted so badly to be on Disney. I was in choir for 5 years. I did cheerleading for 2 years.

Ultimately, I would love to have an opportunity like that for the experience, but, by itself for indefinite work, it isn’t meaningful enough to me. With some consideration and exploration, I found that I want to explore song-writing and taking those lyrics and making them into fully produced music that is independently published on Spotify / Apple Music. My ‘Why’ is rooted in wanting to help people put words to their feelings. I want to help people nail down what’s going on and be able to communicate that to other people in an eloquent/succinct way. I love helping people learn and communicate.

My brother also asked if he could shadow me for a week for his senior project, and that was so exciting of a request. The prospect of teaching and guiding someone was invigorating.

I also reflected and realized that most of my freelancing so far has been erring towards teaching people how to do the things they want to do. I’ve been giving feedback and advice on how to reach their goals beyond the cut and dry tasks they’ve been asking me to complete.

So with those three events in mind, I noticed a trend. I love teaching. That is where I find meaning in my work.

Adjusted Plan

I took some time to jot down what I can teach, in what formats, and what other tasks I should take to strengthen my ability to succeed in doing this.

I’m going to start writing educational content in article format, and also create YouTube videos. I really love offering free education.

I’ll also write some lyrics and make them into songs that I can publish.

I’ll be doing this while also still freelancing (for now). I’ll use my freelance work to guide my education. It will show me what people have a need to learn.

I’ll let you all know, but FIRST I need to finish the work for my clients.

Alright. I’m signing off. I’ll try to update more regularly.

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Kassandra Zimmerman
Who Asked For Your Opinion

I’m here to write after reading, experiencing, and synthesizing.