Diego Design Writing

The New Office

Essay —

It’s been a long time since I updated anyone on my life and at the end of this year, it feels like much is coming together.

I’ll avoid a self-indulgent recounting of the year and instead leave you with some inflection points.

I think often of the story of the businessman and the fisherman, and today, I wonder: what’s my version of fishing?

In the world of careers, and particularly in startups, it seems like every founder is chasing a big exit that will make them a centimillion-if-not-billionaire. Then, with plenty of money in the bank, we could cash in and do what we loved to do. If I had that cash-out money already, what would I still do?

Truth is, I would write a lot, I would spend as much time talking shit (and shop) with people I respect. I might move to Paris, Zurich or Vienna1. I would buy lots of nice furniture and a Phoebe Philo handbag. I would spend most of my time in a beautifully lit and impeccably furnished studio. I would focus on becoming well-known and constantly in dialogue with beautiful and powerful people. I would use my well-known-ness to search for a lovematch, and love them incessantly.

All of those things are very much in reach.

I have written on a goal sheet, “Whatever you think you can achieve, think more, and think faster.” The fact that my goals as listed above are straightforward and in reach, these words ring true. Perhaps the only thing I’m missing is the mental cliff jump to make them reality.


With the mission of achieving and sustaining those not-so-distant dreams, I am evolving from an independent freelancer to a personal enterprise. A private office2, of sorts, with a staff, business plan, metrics, and all.

1. To fund the dream: Client work

2. To create perpetual motion: Publishing

3. To leave room for surprise: Ventures

Each of these pillars supports the other. In particular, the publishing (and associated publicity) is key to driving demand for client work and future ventures.


Today, I’m freelancing with relative success, but there are a few points of tension:

So, some changes need to happen:


Overall, I have done poorly at marketing myself as a designer, writer, founder, and person. Publishing online is the way to remedy this.

One preliminary step I need to define for myself is where I’ll publish. The simplest version should be a blog on my website, which will go along with a slightly larger redesign that explains what I do.

Once that’s set up, there are two categories of publishing that matter to me:


I’ll be writing stories about the projects I do professionally. These will help close new clients and position my expertise in the world of creative services.


Premises like3:

And on social media, I need to share more of what I’m reading and thinking about, in short form content. Some ideas:

The editorial mission of each of the above categories is different, but ultimately all should serve to make me more visible as a designer, writer, and founder.

An exciting development in the publishing aspect of the business is that I’m enlisting the help of an editor, a friend, . will help take my early drafts and push, pull, prod, and poke at the concepts inside. They will also be tasked with being a project manager of sorts, making sure that I take a look at drafts and publish on a consistent basis.


These are the experiments for big, sustainable, scalable revenue. Long term, these seeds are my escape from selling time, and to do that, I have either to develop breakthrough products or build a company with a clear path to profit and a high valuation.


So far:

We submitted to YC and didn’t get an interview, likely because we’ve known each other for such a short amount of time, and it prompted a thought experiment for me: if we got a $500,000 check today, what would we even do with it?

We’d do simple things. Like marketing and testing and trying our own product out. So, to make progress, we’ve decided to do just that.

At first, I’ll fund it with my own money, and at some point we can take a very small check to start lending—maybe $50,000—to bring it to life. In the meantime, our task is to make Terms popular and well-known and loved in the creative community.


I’ve been thinking a lot about publications like Doomberg, 032c, Puck, Grant’s, and how much (light) envy I feel for what these teams have created. Following that envy as a guide for what I want seems smart — it’s what I keep talking about and am obsessed with.

I would love to build a publication that earns the respect of scenesters, writers, influencers, and publishers alike. Mainly, I’m interested in launching an audioblog. Not a podcast — an audioblog.


Get a studio. I reached out to a handful of spaces, and saw one in Tribeca, but ultimately did not decide to rent it. Long term, I want to get my own office space, but at the moment it feels like it would be too lonely and I don’t have enough of an orbit around me to feel social in my own space.

Nonetheless, it remains a medium-to-long-term goal.4

More great friendships. and I are on rocky terms, and I’m unsure we’ll continue to be friends when she’s back from . This breaks my heart even though it may be the right thing to do. I have many great friends otherwise: , , , , , and , for example.

I want to expand my friend group to include people who, in the next 3–5 years, will be taking off in interesting careers. I would like to know tomorrow’s Brenda Weischer and Lauren Sherman before they become who they are destined to be.

As far as dating goes, I’m in no rush. I know what I want, and as with all matters of the heart, I’ll know when I find it. was an interesting case at the end of this year, for a few reasons, and I’m glad to report my ego isn’t so hurt that it didn’t work out. That I don’t need to challenge the situation is a sign of maturity I didn’t have last year.


At the end of every entry in Doomberg’s series, The Work of My Life, they include some metrics of their progress as a publication. They measure their posts and followers. (I like that these are, for the most part, cumulative. Any forward progress is good progress.)

I, too, have some metrics, and they’ll map to each “division” of my “office”.


OCTNOVDECRevenueAfter taxes5Expenses( )( )( )P/L( )( )

This year’s bottom line is not positive. I lost since the year began. It was a rocky year, and it doesn’t feel at all representative of how I want to manage my money going into 2024. Many things that were unstable…

…will not be unstable in the coming year. even then, a handful of expenses (and many handfuls of smaller, ~$400 purchases) made this year a loss. next year: fewer clothes, no Grant’s conference (or subscription), and I’ll try my best not to afford anymore handbags. I’m back on mom’s Amazon account to buy all of my books, which alone should save me a couple grand.

From here on out, the rule is this: I can spend my profit in a given month. but no month, from here on out, should ever be a loss.

Aside from the general chaos of this year, I think my poor understanding of my after tax earnings has contributed to my spending. In YNAB, it’s easy to think that I have earned and am keeping more money than I am, because the money I set aside for taxes appears as an asset, even though it’s really a liability. I might try to set that up as a debt in YNAB, but for the purposes of these reports, I just need to do the math and account for it immediately so I don’t see it as true earnings.


So far, my publicity efforts have amounted to zero. I tried to post a handful of book reviews a few months ago, but they never quite felt like real efforts. I want to post much more naturally, a la Brenda Weischer, and i want to post higher-value, a la Lauren Sherman.

So, in the words of Pema Chödrön, I’m “starting where I am”:

My next efforts will include:


1 This needs more unpacking, but I think my desire to move away from New York is because I don’t feel like there’s anything here for me, and that’s not true unless I don’t put myself out there. I’m constantly searching for wherever gravity is, and New York has that gravity, but for some reason, I’m not tapped into it. I need to rediscover why I’m here because it’s not to chase the dream of a West Village townhouse and settle down.

2 I feel like there’s a great opportunity to name this practice something clever or weighty. I love names like Terms-Eccles, Proenza Schouler, and Berner Kuhl, and some sort of compound name like this would make me very happy.

3I apologize if these don’t quite make sense on first read. I wish them to be intriguing enough for someone in the wild to click on. They will rely heavily on great subtitles.

4 It’s worth saying that I have a strong apprehension about staying in New York. I can see myself falling in love and that doubt falling away instantly, but for now, I keep thinking about Zurich, Vienna, or Paris, where — if I had a visa — I could afford way more apartment & studio, for way less money. Perusing the france-visas.gouv.fr website lightly, this seems very possible.

5Astute observers may notice that this proportion isn’t quite the above revenue amount minus 30%, and this is because is paying me as a W-2 employee and thus my taxes are already accounted for.