The 10 Big Money Questions With Holly Trantham

It’s been a pretty crazy year for TFD, and within that already-crazy year, a pretty insane summer. We’ve been writing and designing the book with every spare moment, and in the crunchiest-of-crunch-times, had to say an unexpected goodbye to our outgoing (and beloved!) Managing Editor, Rebecca. I’d be lying if I said the past month in particular didn’t feel like some kind of cosmic test: can you make it all work, get your manuscript in, find a new member for your tiny team, and get ready for FinCon (which Lauren and I are headed to in exactly two weeks), all without losing your mind or making your boyfriend feel like an abandoned piece of furniture?

Without being totally out of the woods yet, I’m proud to say that we have mostly made it through, and it’s in no small part thanks to the incredible Managing Editor that we found (or rather, who found us), Holly Trantham. Holly is a smart, funny, chill-in-the-best way writer and editor whose first piece for TFD last week still has me re-reading it and cracking up. She’s been a member of the TFD community since pretty much its inception, reading, commenting, and watching the conversation unfold. She is beyond excited to become a leading part of our community, and we’re beyond excited for you guys to get to know her better. She has been a life-saver in such a crazy time: someone who jumps in with both feet and can’t wait to learn more, which is a quality everyone on the team could frankly be learning from.

All of that to say, we want you guys to get to know her better! You’ll be seeing her a lot around the hallowed halls of TFD, and we feel that the best way to introduce her is with the famous 10 Big Money Questions. So let’s get into it!

1. What was your relationship to money growing up?

Money wasn’t really discussed in my household — it was something that kids weren’t supposed to worry about. I grew up in the suburbs of Atlanta, where the richer families tended to show off their wealth with big, flashy houses, second homes on lakes or beaches, and giant SUVs. I assumed that, since we didn’t have those things, my parents weren’t as well off as others in our subdivision. I eventually figured out that they just prioritized things differently. My family had a nice house, but it was a good deal smaller than the average home in our neighborhood. Other families had different areas from my family where they cut back, too. Whereas other kids were raised knowing they would have to go to school in-state, my parents always insisted on letting us pick where we wanted to go to college. We went on nice vacations and I got to do a lot of activities, but because of the flashier belongings people around us had, I always figured we didn’t have as much money.

I found out much later how much work my mother in particular put into budgeting. Now my parents talk to me about money, and I definitely ask their input when I make important financial decisions. But I was taught that it was a rude topic to bring up, as it’s a sensitive subject for most people.

2. Do you feel, looking back, like you got a good education about money, either at home or at school?

In some ways, I think I ignored what could have been a decent education about it at home. I have many memories of my mother explaining the importance of retirement savings, but as a teenager, these were not interesting conversations and I didn’t take as much away from them as I should have. Since I wasn’t involved in budgeting, as it was an activity for the grown-ups, I thought of it as something abstract that my future self would have to deal with.

My parents did always require my brother and I to work during summer break, and I worked as a receptionist all throughout college. Because of those experiences, I learned to save for specific goals. But I generally treated anything I made as extra and wish I’d listened to their budgeting advice earlier on.

3. If you have debt, what are your strategies and philosophies for paying it down?

I have a little bit of credit card debt from about six months ago. I was working as a freelancer and had one specific client that I depended on for a good chunk of my income. I only invoiced once a month, and when one of my checks was over 6 weeks late, I racked up a huge Amex bill so as to avoid spending my savings. I could have curbed my spending habits more, obviously. Regardless, I built up way too much to pay it in full one month, so I applied for a balance transfer card and transferred everything over.

I have a specific amount I budget each month so that I can pay it off before the APR kicks in. Since I do freelance, my income fluctuates, so I don’t have automatic transfers set up. I always pay the minimum as soon as my statement is available to avoid having my credit affected, and I pay the rest of the amount I budget over the course of the month.

4. What is your current job (or jobs!), and how did you get to where you are today in your career?

I’m currently TFD’s Managing Editor, which I am beyond excited about! I’m also a freelance writer and editor.

I was an English major in college and never really had an ideal career in mind. After graduating college and moving to NYC, I was an editorial intern and then blog editor at BUST magazine, which I absolutely loved. In a way, it re-created the college writing workshop environment I missed so much, and I got to work for a publication that really reflected my values.

Of course, that unpaid internship couldn’t last forever, so I eventually found a job as a content writer for a marketing firm, and later became a full-time freelance writer and editor. There are so many writing-related jobs out there that I wasn’t taught about in college. English majors were pretty much expected to teach or never actually use their degree in their career and try and write on the side. I wasn’t taught anything about freelancing, likely because it seems so uncertain in a lot of ways. When my marketing position was being moved to another city and I didn’t want to move along with it, I asked a woman I used to work with for some career advice, and she suggested getting into freelance and gave me some really great resources to get started.

5. When was the first time you negotiated for yourself, at work or otherwise? Can you tell us a bit about that?

Sadly, I’m still very much learning when it comes to negotiation in terms of salary! However, I’ve had a lot of times when I’ve negotiated with myself in terms of how much I think my time is worth. I took a stint as an editor for a startup publication, and when that didn’t work out, I had to transition pretty quickly back into freelancing full-time. I find a lot of projects and clients on platforms like Upwork, and when I started investing time in that again, I changed my base hourly rate. Potential clients (particularly if they need blog articles or copywriting for their new website) almost always try to negotiate your rates down, which makes a whole lot of difference when you’re working on platforms like Upwork (wherein the platform itself gets a percentage of your earnings). So by starting at a higher rate, I allow myself to make what I actually think is a reasonable amount for what the project entails.

6. What is something you understand about money now that you wish you had before you graduated from school and entered the “real” world?

That saving even little chunks of money at a time adds up. I used to only transfer money to a savings account if it was a large amount at once, which was silly — it was years before I actually had anything in my savings account.

7. What is one of your biggest money-related mistakes that you’ve made? What did you learn from it, and what do you do differently now?

I saved basically no money in college. I worked all four years, but whatever I didn’t spend on essentials I just put towards going out (i.e. movie tickets, dinners out, and alcohol). I don’t regret spending some on “fun” things, but I had no savings leftover after I moved to New York, where I didn’t have a job, and I had to get a temp job right away that I ended up keeping for 10 months.

8. What is one big financial goal you still have for yourself? Are you currently using any concrete strategies to pursue it?

I finally opened up an IRA this year — my goal is to set up a consistent contribution schedule. Budgeting with the inconsistent income of freelancing is a challenge for me, so this is in accordance with getting better at budgeting in general.

9. How do you deal with financial setbacks when they happen?

Not as well as I should. I’ve been known to treat myself to a fancy dessert (or two) when I’m stressed about money, then later regret spending that $10. Then I’ll feel guilty and take a long hard look at my accounts and budget and assess where I went wrong. This is a lot better than what I used to do, which was ignore the problem completely.

Something that I’ve learned helps me is to tell the people I’m closest with when I’m dealing with a setback. It’s a lot more stressful to deal with a financial crisis when I feel like I’m trying to hide it from my parents, my boyfriend, or my roommates.

10. What is your personal definition of success, and do you consider yourself successful?

Success for me is doing something you enjoy for work and being able to afford the things you want outside of work. I don’t think I’m successful yet, but I’m getting there! I’m realistic about the fact that work is work, and I won’t always be writing things I think are super exciting. But the more experience I get, the more projects I can take on that I actually am passionate about and the more I can increase my earnings. If I can keep building a sustainable life on freelance writing and editing while continuing to get better at saving and get to a point where I’m picking my projects, I would definitely call that success.