It has been almost 18 months since I began up my freelancing profession — I can hardly consider it! Once I first obtained began, I assumed I had an thought of how issues would evolve. In some methods I used to be proper and in some methods I used to be mistaken. You possibly can learn in regards to the early days of my freelancing in my first and second posts on the topic. In these weblog posts I used to be simply beginning out and getting my ft below me. I nonetheless had many questions and, in reality, stated I’d write a brand new put up after some essential milestones (ahem, paying my first 12 months of taxes). So on this put up I’m seeking to fill in a few of these gaps that I couldn’t reply a 12 months in the past. However I even have realized lots of sudden issues over the previous a number of months, significantly as I’ve met with extra people who find themselves both already freelancing or are contemplating it. So I wished to seize that info as properly.
How We Obtained to The place We’re At the moment
In December of 2023 I launched my very own “solopreneur” enterprise. There we’re lots of causes I went this route. Maybe the most important of them was that the job market on the time was fairly horrible (and it’s even worse as I write this text). I had been in search of a brand new job for a number of months, however no one was hiring. I’m a Gen X-er and my era has been hit fairly onerous by tech layoffs and the rampant ageism that’s frequent amongst tech firms. It was a tough tablet to swallow having over 20 years of expertise within the discipline and but being seen as somebody who couldn’t study and adapt to the ever-changing tech panorama.

On the identical time, I additionally actually wished to craft a distinct life for myself. My burnout and stress degree in company had actually gotten out of hand. It had gotten so unhealthy that I had not been capable of swallow strong meals for months. I’d recurrently get hives and cellulitis requiring medical intervention, significantly if I had to enter the workplace. I wasn’t sleeping, I wasn’t doing something exterior of labor like hobbies (as a result of I used to be at all times at work and even after I wasn’t, I couldn’t unplug), and my psychological well being had actually taken a nostril dive. I knew one thing wanted to alter and, for a very long time, had purchased into the fallacy {that a} “change” could be to discover a totally different firm to work for. Nevertheless, in interview after interview throughout my profession, I found it was fairly uncommon to discover a place that shared my views on work and its relationship to life. I work to dwell, which means work is the factor that I do in an effort to afford my life. I do NOT dwell to work. Some individuals do. Some individuals are blissful being fully chained to their desks, having themselves and their existence tied to their jobs. Some individuals simply actually get pleasure from engaged on an issue morning, midday, and evening. I’m not one among them. I’ve a household that wants me, associates I like to hang around with, and I’ve hobbies I get pleasure from. And I wasn’t attending to do any of that. After one significantly unhealthy day at work, I got here to the conclusion that I may truly create that work setting I used to be in search of reasonably than attempting (in useless) to seek out it.
One other issue that saved me tied so lengthy to company work was the truth that I’m the first (and typically sole, since my partner works a seasonal job) breadwinner for my household. So there was actually worry in going into this. I seen working for an organization as being the one potential steady revenue. And but we’ve got lately seen company layoff after company layoff in an effort to try to save the corporate a bit of extra money and make the shareholders blissful. (Temporary apart: do you bear in mind when Wall Road used to punish firms who did that??? Ah, the nice ole days.) Now we have even seen the traditionally extremely protected US authorities jobs develop into plagued with layoffs. So I humbly counsel that this view of company employment as being “protected” is simply an phantasm.
So in dialogue with my partner, we determined that I’d go solo. I created an LLC to tackle work and reached out to my community through a LinkedIn put up to allow them to know what I used to be doing to try to drum up enterprise.
Quick ahead 18 months. I’ve been fortunately employed within the freelance world with a small handful of purchasers. Working with my community, I used to be very lucky in that I used to be capable of simply change my company wage. Higher but, I’m doing it by myself phrases. The issues I hated about working in company (meaningless efficiency opinions for a elevate lower than the rise in the price of dwelling, ridiculous required “don’t stare into the solar” trainings, asking permission to do essentially the most mundane of issues like purchase a e-book for my persevering with schooling or attend a convention that I had been requested to talk at, and many others.) at the moment are lengthy up to now. Good riddance! And I’m additionally happy to report that I did handle to get my well being (psychological and bodily) again in examine. It took a number of months, however I started to have the ability to swallow strong meals and began dwelling my life once more.

Well being Insurance coverage: The 800 lb. Gorilla within the Room
What follows goes to be a really US-centric perspective on freelancing. I envy these of you who dwell in international locations that offer you medical insurance. Right here within the US, the place I’m presently based mostly, we aren’t as lucky. Medical health insurance is costly. And, in reality, its price retains many individuals from freelancing.
We’re lucky in that my partner’s seasonal job gives us medical insurance in the course of the season (the winter ski season). Nevertheless, that season is just 7 months of the 12 months. Which means that we had to determine what to do for the opposite 5 months. Throughout my first 12 months working as a freelancer, I needed to have knee surgical procedure whereas nonetheless on that insurance coverage. This meant that I had reached my most out-of-pocket (OOP). We determined that we’d put the household on COBRA in the course of the off season. For these not accustomed to COBRA, it’s a US regulation that permits individuals to briefly keep on their medical insurance following the top of their employment as long as you pay your full month-to-month premiums, together with the portion paid by your employer. We had first rate insurance coverage by my partner’s firm…actually not C-suite degree insurance coverage, however fairly good. For our household of three (my partner, myself, and my teenager), this got here out to $3000/month. Sure, you learn that proper. It made sense on the time with the above logic, however had we actually sat down and calculated out how a lot it saved us by me being at my most OOP, it actually wasn’t the correct resolution.
This 12 months, we determined to go onto the open market, which you’re allowed to do exterior of the open enrollment interval with a qualifying life occasion. (The tip of my partner’s seasonal job is taken into account to be a kind of.) This brings our month-to-month invoice to about $1000/month for the entire household.
Whereas it appears apparent that this is able to be the higher selection, there are literally lots of issues to think about with this resolution. For instance, whereas the month-to-month premiums are much less on the open market, the protection is nowhere close to pretty much as good as what we’ve got in the course of the season. Ought to you end up on this scenario, I strongly advocate speaking with an precise insurance coverage dealer to go over the professionals and cons of every strategy. Additionally, it is rather vital that stated dealer be positioned in your space. We talked with individuals within the closest main city (which is 2 hours away) who had no thought which healthcare suppliers actually settle for sure insurance coverage in your space. Professional tip: simply because the insurance coverage supplier’s webpage says a sure physician is in community doesn’t make it so! These webpages are often outdated and are advertising and marketing instruments: they know you wish to see that a complete ton of docs are coated in your space, even when they aren’t accepting that insurance coverage anymore! Ask me how I do know…

Taxes
Let me start this part with the vital caveat: I’m not an accountant or an legal professional. Every thing I’m about to say right here is predicated on my expertise and is my opinion. And, once more, that is all going to be coming from a US perspective. DO NOT PURSUE A CAREER FREELANCING WITHOUT TAKING TO PROFESSIONALS IN BOTH OF THESE ARENAS!!!
OK…now with that out of the best way…
I can not stress strongly sufficient how vital it’s to arrange your small business correctly to be able to receives a commission and pay taxes as it’s good to do. In dialogue with my tax accountant and legal professional again after I was getting began, we determined that my firm would initially be arrange as a single-member LLC. Let’s break that into items.
First, let’s take a look at the most typical enterprise buildings for freelancing work: LLCs and S-Corps. It is very important contemplate establishing below one among these buildings as a result of they provide you authorized legal responsibility safety. The very last thing you need is a few upset shopper attempting to come back after your private property as a result of they’re sad along with your work!
There are tax implications on which of those choices you select involving what portion of your revenue is subjected to self-employment tax, which is round 35%. Usually talking although, LLCs are simple to arrange and don’t require company formalities like board conferences, company resolutions, and many others. S-Corps require extra formality, however the profit there’s that you just solely pay the self-employment tax in your wage, not on distributions. (Once more, seek the advice of with the professionals to study the ins and outs of that bit!)
I made a decision to go the straightforward LLC route. However no matter what you resolve, listed below are the issues I realized from now having truly achieved my taxes for a 12 months on this modality.
- You will have to file quarterly estimated funds in your revenue. When you’re in company, your employer takes taxes out of each paycheck. If you work for your self, that isn’t true. That you must make funds 4 occasions per 12 months. Your accountant will help you’re employed out what these funds might be.
- ALWAYS maintain your small business funds 1000000% fully separate out of your private funds! This implies it would be best to have a enterprise banking account and you’ll pay your self (referred to as “taking a draw”) from that account. Have a debit card related to that account. Don’t use that card for something aside from enterprise bills! Don’t use your private accounts for enterprise bills. Belief me: it will prevent a TON of time at tax season!
- Get no matter bookkeeping software program your accountant recommends and provides them entry to your books. In my case, my accountant prefers Xero. This software program permits full adjudication of the books.
- Your accountant might be getting ready a 1040 Schedule C (“Revenue or Loss From Enterprise”) for you. The proper software program selection from #3 will assist them do that. Basically, what you’re getting ready in it is a full accounting of your small business’ revenue, bills, price of products offered, and many others. With the right software program linked to your small business banking account (and assuming that the solely factor you do in that account is enterprise associated, proper???), that is basically ready with the clicking of a button.
- Maintain. Receipts. For. EVERYTHING. Your small business bills are tax deductible. So is what you’re paying out of pocket on medical insurance. For those who get audited, you’ll completely want this stuff. Get within the behavior of simply doing it.
Keep in mind that as your small business turns into extra difficult, so do your taxes. For instance, I acknowledged that my enterprise is a sole proprietorship LLC, which means I’ve no different workers. Over the previous 12 months I’ve had a number of individuals attain out to me asking if I may rent them into my enterprise. There are vital tax implications in doing so and, as traditional, I like to recommend speaking along with your accountant about them.
If there was one piece of recommendation I must get began proper it might be this: I actually can’t emphasize sufficient how vital it’s to maintain your small business and private funds separate. The solely time cash ought to combine from your small business checking account to your private one is whenever you pay your self. This can make your tax life infinitely simpler when your accountant doesn’t should try to create Schedule C from a complete collection of financial institution accounts, weeding by what have been precise enterprise bills and what have been private. And belief me…you wish to maintain your accountant blissful!
Concluding Ideas
There are various methods to start out freelancing. You is perhaps lucky to find a approach to get began as a facet hustle the place you don’t have to fret but about discovering insurance coverage but or needing to totally change your wage instantly. Or, like me, you would possibly get thrown rapidly into it full time. No matter the way you get there, these are two of the most important hurdles you could overcome to turning into profitable in freelancing.
The insurance coverage query is doubtlessly going to be altering quickly because of the politics within the US proper now and the uncertainty across the open market. As for taxes, I like to recommend rapidly adapting the mindset that you’re an official enterprise, particularly if you’ll go all in and freelance full time, and set up enterprise formalities in the case of funds instantly.
I’ve been very lucky in that issues have been taking off for my enterprise as I study extra in regards to the wants of these serious about contracting with me. So hopefully I’ll have an replace quickly about some new methods I’m seeking to develop my enterprise!
