Personal: Thoughts On My First FULL Year As a Freelancer

Can you all believe it??? It’s been 365 days since I put in a two weeks at my 9-5 job. Until I dive into my first year, how it went, struggles and successes, let’s start at the beginning for those of you who are new around here.

 

After a 5 month maternity leave from my job as Community Manager at the app letgo, I returned to work. It was one of the hardest days of my life dropping off Hudson at daycare, and I quickly realized that it wasn’t something I could sustain, mostly because I was also running this blog, and my workload continued to increase. Matt works in film as a camera assistant, so his days are usually long 12-16 hours, so I was essentially running on empty having to drop Hudson at daycare, work full time at letgo, pick Hudson up, and then immediately jump back into working on this blog when he would go to bed. My life felt … pretty sad. I had no time for Hudson, for Matt or for myself and I knew something had to go. At the time I had around 100K instagram followers, and I was booking consistent work that was ALMOST equal to my salary, but it of course didn’t include the healthcare my job covered. That was the scariest part about leaving, BUT we paid out of pocket and found a comparable plan, and I QUIT. 1.5 months after I went back to work, I said goodbye!

 

A Big Break

Part of my decision to leave my job was because of a travel opportunity that seemed too good to pass up. KLM had reached out to us, and asked us if we wanted to travel through Europe all summer and create video + photo content for them. To this day, I consider this a lucky break. Yes, I had been running my blog for 6 years prior, but for some reason I did not feel worthy of this INCREDIBLE opportunity that I feel pushed my growth to the next level.

So a few weeks after I became a freelancer, we left for ItalyScandinavia and South Africa!! Around this time I also began to work with Kyle, my manager. It was risky to me to make this leap so quickly into freelancing full-time, but I felt like I could focus more on the content creation piece and on Hudson (who was now with me full-time) if I had someone else pitching me, and signing all of my contracts. In hindsight it was THE. BEST. DECISION. IVE. MADE. YET. Because of Kyle, I was able to travel, be the best parent I could be and still know that my e-mails were being responded to!

I’m not sure if the universe could just sense I was a full-time freelancer, or if my timing was just right, but it was almost instantly that I started to feel BUSY working for myself! From various campaigns to NYFW, I was working and mom-ing and traveling and it felt amazing (but also super hard, to be honest) Hudson has always been a slow-to-warm-up kind of guy, and for a while there it was very tough to get much done, but we somehow made it happen and continued to travel and blog and shoot.

For me, the hardest part has always been the juggle of it all with trying to be the best parent I can be to Hudson. From 7 months until 13 months, it was just Hudson and I every day! Any photos that I posted without him in it usually had him in a stroller right next to Matt as he took the pictures. As most of you know, babies are a handful, so it was usually pretty high stress trying to get things done with Hudson around.

Hudson and I traveled to Chicago together for a job with Airbnb, we picked apples and shot a video for Hello toothpaste together, and to be honest he was right there as I grew my blog and my brand smiling at me (or crying ha) from the stroller as I posed silly in pictures. It makes me tear up + super proud to think that during that super tough first year of Hudson’s life I also grew this thing and was able to carve out time to work and make this a priority.

Anyway, back to the year, I attended NYFW in September, spent a ton of time in upstate NY in October and also MOVED to our house,

I also went to Mexico with Noelle, my first vacation away from my family since becoming a mom! Around this time I started to really feel like WOW I am doing this thing, and this is now my life. When you quit your job to work for yourself full-time there’s always this little bit of doubt, like will the work go away, or will I end up back in another job. I think it took until November for me to realize I won’t be going back to a job for a while, because this choice I made ended up being the right one. Around this point I think I had grown my following from 110K to 170K.

By December I realized that having Hudson with me 24/7 and trying to work on this job that had totally erupted into much more than it was a few months back was nearing not possible any longer. December of this year was insane. I really wish I could go into extreme detail (Although I am sure it would bore you all to death, if you are not bored already) but my workload was heavy, Matt’s workload was heavy (even though he also shoots everything for me) and Hudson was along for the ride! Our New Years resolution was BALANCE, and finding a way to normalize this freelance life, even just a tiny bit.

When we came home from Nicaragua and Miami after New Years Eve, our first step to normalizing was finding a daycare for Hudson. It was a really sad step for me, because part of the reason I initially left my job was to spend every day with Hudson, but it’s only for 2 days a week VS 5 days a week, and it is great socialization for him too. Thanks to daycare, Matt and I can now plan days where we shoot – meaning I now find a location I love, plan out our shoots a bit more, and can devote more creativity into the end product. At the end of the day, I want to be proud of what I produce, and make the companies who trust me to hire me proud! So I felt like this was the first step in the right direction.

I also have more days (like the one I am living this moment) where I can sit down and write out blog posts consistently! This one took me about 2 hours to write, which I would never get with a toddler running around. So 1 year in, and everything is starting to feel a lot more manageable! We set aside specific days to shoot sponsored work (and shoot unsponsored work in the moment!), I have an incredible manager who helps with contracts, and I’ve consciously made the decision to not grow my team to any larger than this, and to invest the money I am saving into travel, experiences and clothing to make photoshoots more exciting!

Questions from instagram:

BENEFITS OF FREELANCE VS 9-5?

Okay so this one is something I think about a lot – I really do miss the group setting of working an office job. I loved the camaraderie of going to happy hour with the team, and working together toward the same goal. Blogging is very independent and when something great or awful happens, it’s only really effecting me. You also never truly stop working. When it’s your own thing, it’s around the clock unless you make a conscious effort to stop your work and not look at it. The plus is the cap on pay – there is none. The amount of time you put in can translate directly into a pay increase if you work hard, get lucky, meet the right contacts, etc.  Would I go back to an office job? Totally. Just not right now.

HOW DID I KNOW WHEN TO MAKE THE LEAP?

I made the leap when I was making the same amount of $$ from my blog as I made from my job. I know it isn’t strictly a financial decision, and a lot of i has to do with the happiness and freedom factor, but I contribute to my family and that really mattered for me. I was also booking consistent work, had around 110K instagram followers and felt like I had to say no to good paying jobs because of my 9-5. That’s when I knew it was time.

THINGS I’VE LEARNED

Save your receipts for tax write-offs

Create a schedule even if it’s created by you, and you have the power to change it

Stand up for your brand or business, because you make the rules

Make connections, because supporting eachother is always the best way!

Hire a reliable accountant, and keep VERY good records of your payments for tax purposes. We pay quarterly taxes

THANK YOU ALL SO MUCH FOR STICKING WITH ME THIS ENTIRE YEAR AND ALLOWING ME TO DO THIS JOB!!!!!!!!

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