Things I've learned in 20 years of blogging

Hi, my name is Cheryl, and with my right sidebar as proof, I've been writing this blog for 20 years. Here's how it all began: Picture me, a 25-year-old living out her Carrie Bradshaw fantasies in early 2000s New York City and working in magazine publishing as a copy editor who'd rather be writing about fashion than proofreading stories about beer and football (I worked at a men's magazine). I knew people who had LiveJournal pages (remember those?), but then I heard about a platform called Blogger, so I decided to give it a try. I didn't quite know what I was doing at first—to save you the embarrassment (on my part) of having to read my cringey old writing, I'll provide a high-level recap—but after dabbling in commenting on other writers' work and doing TV recaps, I hit my stride listing all of the sample sales in NYC every week, as well as reporting on the ones I went to. I then expanded into shopping guides and halfway through 2006 (lol better late than never) I finally started incorporating photos. In September 2006, I was among the first group of bloggers ever given press passes to New York Fashion Week; I attended every subsequent season until I moved to San Francisco in 2013. I fostered relationships with PR agencies, got invited to all manner of events, and developed somewhat of a following. I started a partnership with The Find, a shopping search engine that was eventually acquired by Facebook. Internet shopping was growing by leaps and bounds, and I was spending hours every week compiling all of the sales, online and in person, and to be honest, I was getting a little burned out, both from the blog and from my day job and from the general battle that is living in New York City. A new social platform called Instagram started to take off. I took a new job in San Francisco, moved across the country, and pretty much blew up my life. When I wrote an ode to a pair of sweatpants, I knew that, after 10 years of blogging, I had lost the spark. I stopped blogging, and I didn't think I'd start again, until I realized I was about to turn 40 and had no idea how I was supposed to dress anymore. I went to Vegas, won big at the blackjack tables, drank far too many vodka-sodas, and decided to stage a comeback. Blogging had changed since I left—it was starting to be called influencing, and it was shifting heavily to video and social media—but I decided to confront my fears, put myself in front of the camera, and get more personal. That was 7 years ago, and now here we are. Being a wise Blogging Elder who's reached the introspective point of her career, I thought I'd share what I've learned in 20 years of blogging. 

Be an early adapter

I'm proud that this blog has been around for 20 years, and even as embarasingly TERRIBLE (don't look!) as my writing was in the early days, I'm glad I've (mostly) stuck with it this entire time. I was glad I hopped on Twitter (R.I.P.) on the early days, when it felt like a community and not a bunch of jerks yelling at each other. I wish I hadn't stopped blogging right when Instagram started to blow up; if I had figured Instagram out earlier...well, let's just say things might have been very different for me career-wise. I still don't have a YouTube channel (and probably never will) and while I'm on TikTok, I'm not really "on" it. Which leads me to my next point. 

Stick with what you do best

I have always loved to write. At the risk of sounding bananas cuckoo, words flow through me like electricity and come out my fingertips. I write all day at my job, then I come home, get on my laptop, and work on this blog. Writing it brings me so much joy, and even if only a handful of people read it regularly, I'd still keep doing it. Being in a profession where my creative work is constantly under scrutiny and receiving feedback from various people, having this blog is such an important outlet to me, because it's 100% mine and I am fully in control. That said...

Don't quit your day job

I read somewhere that 80% of kids under 18 want to be an influencer when they grow up, and I don't even know where to start with that, other than saying thank god I don't have kids. (Kidding! Sort of.) Full disclosure: I would completely love to do Cheryl Shops full time. But also, know thyself. I am not a hustler. I am not even what you'd call assertive, although I do have my moments. I crave the financial stability that comes with a steady paycheck, so I have a day job that I thankfully enjoy. Do I wish I had more time and energy to devote to the blog? One hundred percent, yes. Do I still find it rewarding? Also yes.

Don't do it for the money

When people find out I'm a blogger, the first question they always ask is whether I make any money from it. My answer is yes, though I pretty much put all of it back into the business, from paying my photographer, my web hosting and newsletter fees, and my PO box, to buying things to feature (yes, that means new clothes). Most of my blogging income is from affiliate links; when you click on my links and buy something, I earn a small percentage of the sale, at no cost to you, so thank you for all of the shopping you do—please don't stop! A small part comes from ads on my site, and the rest is from brand partnerships, which I'd probably earn more from if I did more outreach and business development, but again, I never seem to have enough time (but that's ok!). 

Connections are important

I am not a networky person, but I loved the feeling of community that came from being a part of the fashion industry when I was in New York; I do get invited to events here in San Francisco, but I miss the scale and volume of everything there. I've made a lot of influencer/blogger friends online and sometimes run into them at in-person events, which is a delight. Racked (R.I.P.) was an early friend and supporter of mine, and I love seeing other influencers' followings grow exponentially when a more popular influencer features them. I'm a firm believer that all boats rise with the tide, and we as influencers should support each other however we can. 

Always keep learning

I didn't have photos on this blog for the first three years; after using wire photos and screen shots for an embarrassingly long amount of time, I finally invested in a DSLR and started taking my own, as well as creating my own collages and visuals. Now that I work with a photographer, I do my own photo editing in Lightroom, which involves selecting what photos to feature, then color-correcting them and doing some light retouching (I admit to being vain and yes, I brush out my undereye circles and forehead wrinkles; if you knew how to do it, I guarantee you'd do it too). Full disclosure, I absolutely HATE editing photos, but not as much as I hate editing videos. I know "everyone is doing video now"—and yes, that includes me from time to time—but that doesn't mean I have to like it!

Know thyself

At the risk of sounding like your mother, just because everyone is doing something doesn't mean you have to do it too. I really don't get TikTok. I mean, I understand it, but it's just not for me. And that's ok. Right now, everyone is doing a Substack, and while that appeals to me in that they're so writing-focused, it's just another platform where you don't own your content and it could disappear tomorrow. (And it's not searchable, which is how a large chunk of readers find me!) The same goes for clothing trends—you don't have to participate in every single one, especially trends from your youth that are inexplicably back in fashion, like low-rise jeans. As I always say, just wear what you love. I'd what I plan to keep doing for the next 20 years ;) 

OUTFIT DETAILS: Iro shavani jacket | Isabel Marant Etoile dress (similar style) | Celine classic teen bag (similar here) | Silent D boots 


Nancy 's Fashion Style said...

How lovely to read! And 20 years is a very long time. I was on IG a lot but I stopped that, well, I do post when I have a blog post, but it doesn't interest me anymore at all. I just want to devote my time to my blog, that's where my heart is! Thanks for sharing!

Jacklin Albert said...

I found this blog post on "Things I've learned in 20 years of blogging" to be very interesting. It's remarkable how a long-term blogging journey can be similar to an autobiography. Both reveal growth, experiences, and insights, making each post a page in the story of one's life.

I thought the post was well-written and thought-provoking, and I highly recommend it to anyone who is interested in blogging or personal growth.

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Laura B said...

I hear you about not quitting your day job. Collaborations are so fun but can be inconsistent at times. By keeping influencing/blogging/whatever a hobby you can be more selective when it comes to those things. This was a great post and fun to read! You have so much experience!

Gail Is This Mutton? said...

It's a very long time in blogging terms - I started in 2006, but it was a different non-fashion blog. I enjoyed your learnings. Our philosophy is the same, I prefer to stick to what I do best rather than video, and I prefer having my own platform rather than a hosted place like Substack where they could change the rules on a whim. Congrats on your milestone and carry on sharing!

Jessica Jannenga said...

Wow. Congratulations! I enjoyed reading about your journey and what experiences you had in NY and SF. I would love to get a job as a fashion writer full time, but don't know how many of those jobs are out there. I hear you with "dont quit your day job", I am actually looking to get back to guitar, but I also enjoy writing, so I will keep it up. I do think it is important to do what we do best, and I do get tired of being on IG daily.
Best wishes! Love ur style
jess xx

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