Kayleen Cohen hiking

Conquering The Financial-Emotional Rollercoaster of Freelancing

By Kayleen Cohen

The uncertainty of managing finances as a freelancer can be an emotional roller coaster. Here’s how one successful entrepreneur keeps her ducks in a row. 


I recently experienced the entire emotional spectrum of managing my finances as a freelancer in a single 8-hour work day. It began first thing in the morning with anxiety smacking me across the face. It wasn’t even 7:30am, but I was already frantically clicking and typing away on my laptop, feeling like surely the key to everlasting happiness and prosperity was only an email away.

You don’t have enough gigs,” the voice in my head said. “Revenue is down. You’re going to FAIL!” she insisted. 

I clicked over to my financial projections spreadsheet and confirmed the hard, cold, undeniable truth—I’m operating at a loss. 

The next thing I knew I was frantically scrolling through UpWork looking for one-off freelance gigs. Despite running a successful freelance business for 9.5 years, I was in a full blown financial-emotional negativity spiral.

It should have felt familiar, considering I’ve experienced this feeling dozens of times over the last decade of running my own business. My therapist once offered the wise counsel, “you have made it through 100% of the times this has happened to you so far.” The story I was telling myself that morning simply wasn’t true. I have learned tools and techniques, like creating financial projections and signing multi-month retainer contracts which I will share below. 

Later that morning…

Later that morning—yes, that very same morning—I took a 15-minute phone call that turned into a $600 one-off freelance gig. I sighed an enormous breath of relief. As my mind calmed and I returned back to earth, the narrative of my professional money story began to shift. Alas, I was not doomed. Not because of the $600 gig, but because of my ability to obtain freelance gigs.

“Wow, you’re such a boss!” the voice in my head said now. “You have unlimited earning potential, because you are capable of landing all kinds of interesting and unique gigs.” Really? Is this the same girl who was nearly crying while scrolling through UpWork just a few hours ago?

My ability to obtain freelance gigs started 10 years ago when I chose to adopt the title of “freelancer writer”. At the time I worked in a coffee shop, but I told everyone I met that I was a freelancer, and suddenly my latte customers started turning into clients. Since 2013 I have contracted more than $900K in freelance projects, many of which started with a handshake and a title I chose to believe in.

Freelancer, entrepreneur, small business owner, startup founder, hustler, etc. No matter what title you choose (I personally vacillate between a few of those) you have probably experienced a few moments similar to the one above. Where will my next client come from? What is the next big project? Will I be able to afford to keep the lights on in six months if nothing changes? These are the questions we ask ourselves.

Choosing a life of uncertainty

Choosing to be a freelancer or an entrepreneur is choosing a life of uncertainty. It is knowing that many times you will have to leap before the net appears. That nothing is guaranteed. That today could be feast, but tomorrow could be famine.


I just want to give that word some space, because uncertainty is a really icky human emotion. I personally detest being in emotionally uncertain spaces. Like most people, I tend to default to binary thinking. Things are either good or bad. Which doesn’t leave room for uncertainty. It just doesn’t fit in to the equation. That is why most of us will do anything to jump to concrete conclusions instead of marinating in the grey space. 

But entrepreneurship involves a lot of grey space.

Using “Trust Theory”

To wallow through the muck and the mire with one’s head held high requires trust in the universe and a profound belief in your own worthiness. I call my business generation strategy the “trust theory”. I trust that if I operate with integrity and diligence, my work will speak for itself and good projects will find me. So far, this has proved true in the vein of $100K of projects each year. You might feel inclined to throw shade on this theory as too woo-woo, but time and again, dream projects have dropped out of the sky into my lap out of seemingly nowhere, always just in the nick of time.

For example, the $600 gig. While I was busy telling myself a fear-based story about my imminent and inevitable failure, one of my established retainer clients was sending a referral email to a colleague. One email, one phone call, and 15 minutes later the contract terms were negotiated. Just think, instead of pushing myself to the verge of a panic attack, I could have been contemplating the beauty of trust theory and drinking a smoothie while petting my dog.

Enough woo-woo, let’s talk shop

Somewhere between the highs and the lows of entrepreneurship are the infinite lessons, the bumpers that guide us closer to stability, closer to a predictable rhythm. In my decade of self-employment I have learned a few practical lessons that I can share for others currently riding the roller coaster. 

One-Offs vs. Retainer Contracts

While I just rejoiced about receiving a one-off project, this is absolutely not my preferred option as a freelancer. Retainer contracts for freelance services allows you to secure revenue further into the future, make more accurate financial projections, and balance your workload. One-off projects can be a good place to start a relationship with new clients. Offering clients a retainer-based contract benefits them as well, by knowing that their needs will be satisfied by a qualified contractor for 6-12 months. I recommend using a minimum contract duration of 6 months and offering incentives for clients who sign 12 or more months at a time.

Using Freelancer Sites for Gigs

My pride prevented me from exploring freelancer sites (like UpWork, Fiver, or The Mom Project) for many years. One day, however, during a particularly low and panicky moment, I found myself signing up for an UpWork account. To my surprise, I discovered that I could actually set my rates, validate my expertise, and seek out really high-quality gigs. I found a one-off copywriting project that really jazzed my horn. Upon successfully completing the assignment, I converted the client into a 12-month retainer contract. Heck yes!

So, I recommend using these websites as a “shopping network” for prospective new clients. Keep your standards high! Unless, of course, you are just starting out, in which case take every small gig you possibly can and build your portfolio for bigger and better projects! This was my hustle-mentality for my first 1-2 years of freelancing. Keep in mind that these websites capture a significant portion of the revenue generated through their platforms. Personally, I try to earn less than 20% of my total wages through freelance sites and 80% or more through retainer contracts. 

Creating Financial Projections

Making and tracking financial projections was a total game changer for my small business. I had already been operating for more than seven years, dealing with the emotional highs and lows of freelancing in a gig economy, when it occurred to me to make a spreadsheet of all my contracts. Wow, is it just that easy? Yes, it really is.

For more than three years now, I have tracked all of my contracts, month over month and year over year in a spreadsheet. This allows me to project my finances 12+ months out. That’s how I knew in Q4 of 2021 that Q3 of 2022 would be down. I knew before this year even started what my currently contracted revenue would be for the entire year. Tracking your financial projections is as simple as what I’ll provide in the template below:


Client 1$600$600$600$600$600
Client 2$1,200$1,200$1,200$1,200$1,200
Client 3$850$850$850$850$850
Client 4$600$600$600$600$600
Client 5$600$600$600$600$600
Monthly Total:$3,850$3,850$3,850$3,850$3,850

Q1 (Jan-Mar) Total: $11,550 Annual Total (Jan-Dec): $46,200


A simple system like this can provide a ton of helpful financial forecasting information for freelancers and entrepreneurs. This can tell you if you need to be in hustle-mode rustling up more contracts, or if you are potentially verging on being over-committed. By projecting your total gross revenue for the year, you can also manage your expense budget and forecast your tax liabilities. A system like this help remove some of the uncertainty from the financial-emotional roller coaster of freelancing, and while it certainly doesn’t assuage it entirely, it does allow you to see what’s coming at a remarkable distance.

In conclusion, I urge you to trust in the universe, find kindness for yourself when the coaster bottoms out, pursue opportunities from a place of worthiness, and give yourself a gracious runway with simple financial projections.