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The Money Diaries: The 29-year-old workaholic who’s counting down the days until he goes into debt

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Today is another post in the Money Diaries series, which is based off New York Magazine’s Sex Diaries. We’ve collected stories from real people about their spending habits over seven days, anonymized them, and posted them here.


This week’s post is by a 29-year-old graphic designer exhausted from trying to hold down his full-time job, grow his part-time freelance work, pursue his artistic goals and help raise a three-year-old. He’s debt-free but saving nothing, and his stress about money is through the roof. What’s the first change this guy should make?

* * *

Day 1

12:45 a.m.:  Good morning! It’s past midnight. That must mean I’m wrapping up another long night of freelance work. Three hours x $70 an hour = $210. Minus about 25% for taxes, so that’s about $157 net. My wife’s been bugging me to review the weekly budget she emailed me several days ago, but I’m still too afraid to look at it. And tired. I can’t stand to recalculate how many weeks or months until we’re in debt. I’m honestly not sure how we still have cash in the bank. She took a couple years off to raise our son and now she’s having a tough time finding work again. I’m trying not to be bitter that I’m burning the midnight oil doing freelance on top of my day job while she goes to bed early because she’s too tired to put in a little time each night looking for work or doing freelance. What am I supposed to do? Part of me says I need to crack down, cut up the credit cards, watch each penny like a hawk. That won’t work, of course. Part of me says fuck it. I buy a song on iTunes that I’ve been playing on Grooveshark nonstop. There goes another buck. Time for bed.
7:00 a.m.:  My son is up. Which means I’m up. My wife is slow to get up in the morning. I gotta start the kid’s breakfast and feed the dog and pack my lunch and shower and get ready for work. I know I should pack a big, tasty lunch the night before. But I’m tired and have to get to work. So I throw in a can of sardines (which I do like) and some carrots and a soda in my lunch bag. I make eggs for my family, but I have to put mine in Tupperware and eat it at the office. I’m running late.
10:30 a.m.:  Morning break. I walk to 7-11 with my cube mate. The maple frosted, cream-filled long johns are calling my name, but I resist. Save myself $1.35.
1:30 p.m.:  Who am I kidding? One can of sardines isn’t going to make me feel better. Plus, I need to get out of the office for lunch or I’ll go crazy. My office is full of idiots. And at $20/hour, I’m underpaid. It’s depressing when I think about it. Off to McDonalds. $4 and change for a McDouble, two small fries and a large Coke (to keep me awake through the afternoon). I know it’s bad for me, but it’s cheap and easy and delicious and the only restaurant close to my office.
9:15 p.m.: My wife went to yoga this evening, so I watched the kiddo. Finally ate my sardines. Had a beer to relax. Now it’s time for freelance. I make another $100.

Day 2

10:30 a.m.:  So much for resisting that long john. I just wish I could get back to the office before it’s all gone. $1.35.
3:30 p.m.:  Thank god for my smartphone. I can keep an eye on my freelance email while I’m at the office. One client drops a couple rush projects in my lap. Altogether, probably $500 worth of work. That’s great, I need the money. But I don’t know if I have the time. Oops. Time for another boring meeting.
10:00 p.m.:  I’ve started outsourcing some of my freelance to a friend of mine. He’s good, but still learning, so it still takes a chunk of my time to explain, review and polish his work. I give him half of the work and pay him $150 (which he’s glad to get). And I do the rest myself. I wanted to start working earlier this evening, but it’s hard to put my son to bed and go straight to work. I need some time for myself. Which isn’t spent painting – what I really want to do. Mostly it’s spent on Facebook and Twitter. Ugh.

Day 3

11:30 a.m.:  My insurance agent calls with estimates for private health insurance. I want to go full-time freelance, but with my wife out of work and no savings, I don’t think we can afford the transition. Right now I’m spending $8,000 a year to insure all of us through my work. And the coverage isn’t that great. Seems like highway robbery to me. Private insurance should be cheaper.
12:00 p.m.: I use my lunch break to take a nap in my car. Kind of helps.
5:00 p.m.:  I get home to find my wife bought a new welcome mat. This is supposed to help our feng shui and improve our financial situation. All I know for sure is that we’re out another $45. What would really help? Her getting a job.
9:30 p.m.:  More freelance. Mostly admin and paperwork. Necessary but not billable time. I manage to squeeze in an hour to update my blog for my painting website. I haven’t sold anything yet. I just started six months ago. It’s hard to find time to market my paintings – or paint – on top of all my work. I feel like everything is backwards.

Day 4

9:30 a.m.:  I use my break at work to visit my son during his gymnastics lesson (down the street). He usually has a good time, and I love that he has these enrichment activities, but $15 for 45 minutes seems pretty steep. I mean, it’s a group class and it’s not like he’s getting one-on-one instruction from an Olympic gymnast. He does love the trampoline, though.
11:30 a.m.:  I was supposed to have a meeting with my boss about a big promotion I’ve been pushing for for six months, but he’s still dragging his feet and putting up excuses for why the timing isn’t right and what about this and that even though he still says I’m good for the job. I’ve been counting on the raise for months to help cover our expenses (we’re about $1,300 in the red each month), but still nothing. Now he’s suggesting the raise that goes with it might not be as big as I may have thought. Why do I bother?
2:00 p.m.:  Back to McDonalds. Another $4 and change for more junk food. This time I actually brought a lunch, but I needed the comfort food. (God, is McDonald’s really comfort food?) I’m embarrassed about eating McDonalds again so I put the charge on my business credit card (for my painting), which my wife doesn’t have access to.
10:30 p.m.: It’s Friday night. Do you know where your graphic designer is? He’s still working. The freelance never ends and never is enough. Another $105.

Day 5

8:45 a.m.:  Saturday morning. I don’t have to rush off to the office, so I can enjoy a nice breakfast with my family. Then it’s off to do more freelance work. I have a full day of work. My wife collects the week’s receipts so she can update the budget. We track every expenditure. There’s some 75 different categories of expenses. The ship might be sinking, but we’ll know exactly where the holes are. (Everywhere!)
12:00 p.m.:  Lunch. I’ve made $140 so far and spent another hour looking at someone else’s painting blog and daydreaming I had more time to paint. When was the last time I actually painted? Now I’m behind at work.
12:30 p.m.: My wife tells me one of my freelance checks arrived ($1,200) and my direct deposit check from work cleared ($1,200 – biweekly). Then she tells me she paid the mortgage ($1,100), HOA ($200), car insurance ($95), nanny ($400 for a few afternoons a week while my wife looks for work) and gym membership ($127). She also says we’re going to be overbudget (again) for groceries. We’re halfway through the month and we’ve already spent $600 on food. If past months are any guide, we’ll definitely spend another $600 on groceries (that doesn’t count eating out) before the month’s over. The budget is always depressing.
1:00 p.m.:  I break down and look at the spreadsheet my wife sent over. We’ve budget $30 each month for personal expenses. I’ve averaged $24 so far this year. She averages $70. Last month she spent $204 in this category. As far as I can tell, this is mostly her eating out regularly because she’s depressed about being stuck at home all the time.
4:00 p.m.:  My wife is asking when I’ll be done with work. I’m pissed off. How am I supposed to pay for all of this shit when she’s constantly asking me to stop working early or to take a long lunch break or skip an evening? I’ve made another $170 (so $310 for the day), but I’ll need to finish tonight after everyone goes to bed.

Day 6

10:00 a.m.:  Sunday is my wife’s day off. I spend the day with my son and she goes to yoga then can do what she wants in the afternoon. I wish I had a day off.
3:30 p.m.:  I take my son to the gym. For $3.50, he can play in the gym nursery – a great deal! – and I can work out for an hour. Afterwards, I take him swimming at the gym pool. Lots of fun.
4:45 p.m.:  We stop by Sam’s Club on the way home to pick up a few items. They don’t have much organic food (we shop at Whole Foods almost exclusively…when we’re not eating at McDonald’s, I guess). Another $44 at Sam’s. I also stop at the liquor store for a $22 handle of Jim Beam. Helps the medicine go down.

Day 7

7:00 a.m.:  It’s Monday and I’m somewhat rested. I decided against doing freelance last night and just went to bed. I’ll pay for that tonight, but for now I’m rested. Time to start the work week over again.
8:45 p.m.:  My wife tells me we should be contributing to our IRAs. I tell her I don’t know how that’s possible since we’re losing money every month. She says it’ll work out and that I’m supposed to get another freelance check this week. So we have cash in the bank. What about keeping some set aside for freelance taxes? I can’t talk about it. I have work to do. Two hours I have to get done before tomorrow. That’s $140.

In Sum

Freelance income: $1,215
Day job income: $600
Expenditures (bills/family): About $2300 (but that includes some monthly expenses)
Expenditures (personal): About $35

Endless work. With all my freelance, I’ve almost doubled my income over the past year, but I’ve also increased my hours 50%. Thinking about money still gets me upset, and I don’t know how to deal with it with my wife. I’ve been just hoping that she’d get a job and things would get better with the thought that it’s easier to make more than save more. But I’m not sure how long we can keep going before we’re screwed.

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126 Comments

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  1. Man, this guy can’t seem to catch a break. Working non-stop and still getting behind. I’d like to donate $25 towards the cost of Earn 1K for this guy, and then see an update a year later. That would be a really interesting study. Who else is with me?

    • Ditto Brian! This guy works his self to the bone. I’d be up for donating $25 to the cause of affording Earn 1K for this chap…

    • I would talk 1-on-1 first about the financial situation before counseling. You never know, the 1-on-1 talk could turn out really well. That way you’re not having to pay for the professional counseling they probably can’t afford…

  2. I’m the software developer version of this guy: bigger income, but bigger debts, too. I can relate to his situation, down to the significant other trying to get a job and spending money on the sly.

    I want to know what happens to this guy. Hopefully there will be an update? Otherwise, best of luck to you, brother–you have my empathy and I’m rooting for you.

  3. Sounds like he and his wife are not on the same page financially. Key phrase “she took a couple of years off” — probably always a bad financial decision for a family. How could you not have seen the red ink before that decision was made. Tell her to get a job in fast food or Starbucks. She should swallow any pride she has and take anything she can get.

    • As a mom I agree. If I were to stay at home & then couldn’t find a job when I decided to go back to work, I would take almost anything until I could find the right one. She spends so much….I agree with poster above on counseling.

    • “Tell her to get a job in fast food or Starbucks.” Isn’t necessarily a viable solution. They will need some sort of daycare solution for their child. It’s unlikely that a minimum wage job would cover daycare expenses. Thus they would actually be more in the hole.

    • Exactly, I have never understood why people do not take the low paying jobs while they look for work in their field. The only reason I can think of in this example is maybe she is watching the son at home during the day and paying for a nanny with a low paying job does not make sense.

  4. Looks like this guy is able to find some decent freelance work if he has to outsource some of it to others. Here are a few of my ideas:
    1. If the new promotion doesn’t carry any hope of a raise, perhaps it could work with flex hours or maybe one Friday off a month. He could then focus more hours on more profitable (over 8x his hourly pay) freelance work. (~8 hrs @$70/hr- $560).
    2. $600 for two weeks of the free-range, fair trade, organic, non processed, crunchy food from Whole Foods? They already have a membership to Sams Club, time to start using it. You can still get healthy food from Sams Club. You just have to stay away from the jumbo sized packages of hot dogs. (estimate of savings at half the existing Whole Foods budget of $600)
    3. You will probably see some savings from paying the car insurance in a 6 month block instead of monthly (probably only $50 or so savings here).
    4. We only got one side of the story here, but the wife could make a few cuts here. Any family members to look after junior instead of hiring a Nanny? Personal expenses are over 6x what they’re budgeting. Maybe find a gym where you can pay per visit instead of a monthly membership. Once the wife finds a job this will probably help the budget out greatly.

    Just a couple thoughts off the top of my head. Hope this guy gets some good comments from everyone on here!

    • Err..actually the freelance only pays 3x his base hourly wage, don’t know where that 8x figure came from. Haven’t had enough coffee yet…

  5. First thing he should do is have a loooong chat with his wife. She seems to be getting her relaxation in while he works himself to death. This is very unequitable and unfair. How about they stop shelling out $400 for a NANNY (seriously!?!?) and she looks for a job on Sunday instead of “taking a day off”. She gets a day off when her husband gets a day off. They should be in this thing together, if he doesn’t talk to her about this he’s going to end up resenting his wife + money problems = divorce.

    Instead of paying a nanny, his wife could also “swap” babysitting with a few other ladies that want time off & they can rotate….get the free time she wants without costing much.

    Also she spends money eating out because she’s depressed being stuck in the house. How about take their child out to a park & play? Meet up with some other kid’s mom’s and have some social interaction? It’ll be cheaper AND more fulfilling. Being divorced is much more depressing than being stuck in the house all day.

    And shopping at Whole Foods???? At least try for a weekend farmer’s market, where you get bascially organic food without the high price. Many small local farmers aren’t certified organic but they follow the same growing methods.

    • I 100% agree about swapping babysitting hours with other families.

      I’m not sure I agree with his wife skipping her days off…. it might be the only thing keeping her sane. That said, he should find a way to get some time to himself as well.

      His wife seems depressed yet they don’t seem to be addressing the issues that are causing it. There may be ways to aleviate her depression without spending more money. As many other commentors have noted… the resentment is building up. Resentment = doom, relationship wise.

  6. I feel for him. I think most of us who work a lot and try to manage families who may not see everything the same way can relate. based on this diary, I definitely see a few areas for a very fast improvement, coming from the outside.
    1) Cut the nanny and 120/month gym. My gym is $10/month. That’s 500/month savings right there. Have the Mrs. search for work at other times, when you can watch the kid. Maybe that means asking the boss for work at home some days privileges, which it sounds like you have earned.
    2) Cut the grocery bill. 3 people should be less than 600/month, more like 400-500/month for healthy eating. 1200/month is insane. Don’t shop whole foods. Consider gardening. Analyze food receipts for highest ticket items, and don’t eat the top few items, or reduce consumption. Don’t buy prepared foods. You could probably find an easy way to save 500/month here.
    3) Forget the raise in the current job. If you spend 30 minutes a day looking for a new job with higher pay, I bet you could find it within 3 months, raise + promotion included. Then consider leaving or showing it to your boss.
    4) Love the freelance direction. Sounds like you are on the right track for sure. That sounds like a good medium to long term plan. Try doubling your rates.
    5) set aside some time for self reflection. Your wife gets it, why not you? Your work schedule is not sustainable.

  7. It’s sorta hard to suss this one out, partially because I think it’s pretty clear that we’re getting only one side of the story.

    Regardless, however, it is VERY clear that there’s some resentment building up on the part of the author here against his wife. Whether her expenditures are necessary or not, whether her attempts to find a job are enough or not, they need to have a serious sit-down to discuss their respective perspectives on the situation and figure out how to find a happy medium where neither of them feels resentful of the other.

  8. How the hell are they spending $600 on food? They need to start cooking at home, with groceries not bought at Whole Paycheck, because it literally is that.

    I would say he needs to raise his freelance rates some, which would help bring more money in, and then have a serious discussion with his boss. Boss needs to know that if he’s serious about keeping him at the agency, he needs to become competitive with the freelancing rate.

    I’m also seeing a lot of avoidance, he and his wife need to have a serious talk about money, and expectations. They need to figure out a system that works better for both of them. It sounds like he avoids dealing with the budget until necessary, but spends all his time fearing what’s going on. They both have to be involved. I would put both of them on a cash-only envelope system for a while, it’s helped me a ton for expense categories I tend to go over in.

    Being out of work and looking is hard and discouraging and demoralizing, I know. She needs activities to do during the day besides job-hunting, I would suggest cooking from scratch or networking with employed friends at lunch.

    I would cut the gym membership, or find a cheaper one. I just feel bad for them. Hope they turn it around.

  9. God, this was painful to read. Money, stress, relationship problems – each piece makes the others worse.

    I think it’s clear that this guy is underpaid at work. If he’s able to charge $70/hr for freelance work and get repeat clients, it’s ridiculous how little he’s making in his day job. Now that $20/hr figure doesn’t include taxes or benefits, so the disparity is less than it seems. But still, it’s a big difference!

    Under other circumstances I might suggest he try to make the freelance transition. He’s making so little at his day job that with 40 hours a week to work freelance, I think he could replace his income. But he’s currently the sole wage-earner and has a small child, and I can understand that he’s unwilling to take the risk. I think instead he can use his freelance situation to leverage asking for a raise, or possibly looking for a new job.

    Doing either one of those things well means having some time to prep for it, and right now it sounds like time is the main squeeze. I think he’s already on the right track with outsourcing some of his freelance work. Until his wife gets a job, maybe he can outsource some of the non-billable work (administration, etc.) to her, giving him some time to do the research and prep he needs to do to get a raise. Or this might be an area where it’s worth spending money to make money, to free up his time for a week or two to prepare for those negotiations Ramit-style.

    On a personal note, I’ll add that I remember when my husband was unemployed. It was awful for both of us, and based on that experience it sounds like his wife may be depressed. Take advantage of the family’s health insurance and see if there’s something you can do!

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