What self-employed money diarists learned from tracking their spending

Are you self employed and interested in tracking your spending more wisely? Read here for tips about the importance of money management.

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If you've read even a handful of R29's Money Diaries, then you know how much more there is to learn from someone's daily spending than just the cost of their morning green juice. The real lessons lie in the larger details of the diarists' lives—their jobs, their interests, their social habits—and how money fits into each of those. It's these things that let us see a little bit of ourselves in the diaries and think about the role money plays in our own lives.

Take, for instance, self-employed diarists. Whether you're currently out there hustling on your own or are thinking of one day leaving your 9-to-5 to pursue your entrepreneurial dreams, there's so much that can be gleaned from the spending habits of others who are already at it—from how to handle inconsistent pay to adequately valuing your time.

That's why we checked back in with some of our favorite entrepreneurial diarists and dug deeper into what it's really like to run your own business. Ahead, find out what's changed since their diaries were published, key lessons they've learned, and their best advice for those also looking to go out on their own.

A week in New York City on a $34,800 income

This New York-based diarist wrote about her work as a freelance writer, web developer, and bar waitress, which involved negotiating rates with clients, occasionally working out of a friend's loft space, and pouring lots and lots of tequila shots.

Can you give us an update on your business since your diary was published?

"A lot has changed! I've made a ton of progress in my writing and finally feel like I've given the dream to become a writer a chance to develop—although I'm still not making a ton of money from freelance writing. On the other hand, my web developing has taken off and I'm getting requests weekly (who knew all you needed were some good references!). I now charge 30% more than my previous hourly rate, which helps offset the costs of a coding course I began taking to bump up my skill set.

"In September, I made $1,100 and in October I made $1,300 from web developing, whereas I was making no more than $800 per month before. I still waitress, too; my income there is pretty much the same as when I wrote my diary."

What was the biggest lesson you learned from tracking your spending for a week? Were you able to think about your business in a new way?

"Tracking my spending made me triple my [work] efforts because I realized that while I feel like I'm struggling and feel like I'm making so many sacrifices, I do reap some benefits from my boyfriend. I didn't realize how much my boyfriend subsidized my lifestyle for the sake of my alternative employment—even if he isn't paying my bills. A nice dinner on his tab may not seem like a lot, but in actuality, an 'escape' from the money-pinching meal hacks one night a week helps me reset mentally to feel rejuvenated and not feel defeated or have FOMO all the time, but it isn't something I could afford to do for myself.

"I began to see my business as a way to prove to myself and my boyfriend that I'm not abusing him picking up the financial burden for our dates or adventures by lackluster pursuit of my own means to an income. That realization made me take coding courses and really kick things into high gear, so we both can look at my business accomplishments and be able to say 'it all paid off,' without him ever feeling like I was just on a joyride while he was picking up the tab."

What's the biggest obstacle you've had to overcome being self-employed?

"There are two that I've equally struggled with. First, it's extremely difficult to have inconsistent income—especially when it comes to my student loans. When I had a great September, I tossed all of that extra money towards my student debt, but then I didn't get another project for a week and didn't know if any other work was going to come in. I was strapped for cash and asked myself, Did I just screw up? I should've kept some money. Luckily, I ended up having a great October as well, but the anxiety is always there and that's when I wish I just took home a salary every other week. I now know to prioritize an emergency fund because work is NOT guaranteed. I recently opened a high-yield savings account where I plan to keep at least three months of expenses; once that's built up, I'll feel a lot more at peace with the inconsistent nature of my income."

What's been your greatest business accomplishment thus far?

"Being referred! No longer do I have to wait for a random job—clients have told their friends and family about me, and that's why my income increased so much. I also began giving clients I've completed projects for my [direct] email address, so when they do refer me, I don't have to pay a middleman, since most freelancing programs take a sizeable percentage off your earnings. I also learned there's no shame in asking to be referred—I used to be shy about it, but now I realize it's the best way to get new clients."

Where do you hope to grow your business in the future?

"I left [my full-time finance job] to write, not to develop websites, but web developing is proving to be very lucrative and lets me exercise my creative muscles by adding copy or making content recommendations. Once I have a few more projects under my belt, I plan to create a website, showcase a few case studies, and offer web development and copywriting as a package deal. A friend and I have been casually talking about teaming up to create our own digital agency, so maybe sometime down the line that'll happen."

What advice do you have for other women looking to become self-employed?

"Once you gain control of your prices and are able to pass on projects that pay too little, network with other women and share your rates with each other to ensure you're not undervaluing yourself. I have a shared Google Sheet with other women who freelance on various platforms, and we all share our different projects, what they entailed, and what our rates were. On multiple occasions, those women made me realize I needed to up my rates or that I needed to decline a project altogether because it just wasn't reasonable. They also taught me to value my time—just because $400 is a lot doesn't mean it's enough for the project at hand, and there's no way to make those calls without a network of peers to discuss with."

A week in Missoula, MT, on an $18,000 salary

This diarist, a freelance graphic designer living in Montana, wrote about enjoying her flexible work schedule, procrastinating in coffee shops, and what it's like juggling projects for multiple clients at once.

Can you give us an update on your business since your diary was published?

"I've had a few other projects come my way, mostly through friends, including a regular 10-hour-per-week gig editing photos. It's not the most fun, but it fills in the gaps and keeps me in a work mentality."

What was the biggest lesson you learned from tracking your spending for a week? Were you able to think about your business in a new way?

"The biggest lesson I got from tracking my spending and time is that I'm rather careless with both! I got a lot of flack for coming off as lazy, but a few other freelancers understood I was in between projects and that's what this lifestyle is like sometimes. Yes, I could always be doing something to further my business, and I absolutely 100% want to improve in this area, but I also need time to recharge. Even though I enjoy my work and am very lucky to work for myself, I don't live to work. My Money Diary experience taught me to have more balance—to take my work more seriously and be humble but still watch TV all morning if I can and want to."

What's the biggest obstacle you've had to overcome being self-employed?

"Besides money insecurity, there's a lot of comparing yourself to other freelancers—whether it's the number of projects or how interesting the projects seem. Working with small clients with limited budgets doesn't always allow me to be as creative as I could be, but I'm happy to be helping small businesses get more awareness and present themselves more beautifully. I've also struggled to take the work I do seriously and not joke about it being a hobby. Recognizing my skills and value is an ongoing journey."

What's been your greatest business accomplishment thus far?

"Managing the business side of things has been a big shift for me. It sounds obvious, but being prompt with emails or sending a response to confirm I understood something is not something I would have done a few years ago. I always prided myself on being able to take a project and run with it and not be what I thought was a 'nuisance.' I've learned that being communicative is not being a nuisance, and it will make everyone happier in the end."

Where do you hope to grow your business in the future?

"I'd like to continue to work with small colleges to attract prospective students. I'd also like to work for environmental and social causes I support. In the immediate future, I hope to add one or two more steady clients (ideally schools) to do promotional materials for, and then I'll add other one-off projects that stretch my skill set into the mix."

What advice do you have for other women looking to become self-employed?

"Take your time and be gentle with yourself. Try to have a large financial cushion when you make the leap. Burnout is real, so give yourself a few extra days when scheduling projects—you can always send work in early! And know that you've made it to this point for a reason, you know what you're doing, and, if not, you have the skills to figure it out."

A week in New York City on a $115,000 salary

This hospitality entrepreneur based in New York wrote about what it's like to work with friends, ask for a raise, and share a workspace.

Can you give us an update on your business since your diary was published?

"Drawing up to its first anniversary, my business has finally evolved into a more defined shape. The main revenue center started to generate steady cash flows, but not all projects went down the expected paths—some promising ideas died in the cradle at no small cost. My young team gets frustrated, but cheering up is the only way to carry on for the journey ahead. We are reminded that entrepreneurship is a bumpy road."

What was the biggest lesson you learned from tracking your spending for a week? Were you able to think about your business in a new way?

"I always keep a personal book, so the numbers from the particular week I tracked for Refinery29 did not surprise me. However, journalizing my detailed thoughts around each spending decision exposed how I sometimes expensed a disproportionate amount of mental energy on insignificant savings. I learned the lesson that there is only so much you can save—that I'd much sooner become a millionaire by investing the energy to explore additional revenue sources than counting every penny."

What's the biggest obstacle you've had to overcome being self-employed?

"Time management and self-discipline. There is a strong temptation to procrastinate when you are free to utilize your time any way you want."

What's been your greatest business accomplishment thus far?

"This is my first year to assume the identity of an employer, and I am proud to provide for my employees. It's exceptionally empowering to have created something that brings people together."

Where do you hope to grow your business in the future?

"Due to the nature of my business, we will be restricted to the local market for the near future."

What advice do you have for other women looking to become self-employed?

"It'll always feel like a leap of faith, because nobody can ever be fully prepared for the unknown. If you believe this is right for you, make the move and take it!"

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Article copyright 2018 Lucy Meilus from Refinery29. Reprinted from the December 17, 2018 issue with permission from Lucy Meilus.
The statements and opinions expressed in this article are those of the author. Fidelity Investments cannot guarantee the accuracy or completeness of any statements or data.
This reprint is supplied by Fidelity Brokerage Services LLC, Member NYSE, SIPC.
The third-party provider of the reprint permission and Fidelity Investments are independent entities and are not legally affiliated.

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