I Knew I'd Figure it Out: How I Made Money When My Business Wasn't Supporting Me

*There are affiliate links in this article*

I admire every person that ever tries to start a business. A piece of me had an idea of what I was getting into when I left my engineering job to become a professional cuddler fulltime (yes really), but really... I had no clue what I was getting into as a millennial with student loan debt and a modest amount of savings.

Honestly, doing this wasn't part of The Plan. The Plan was to work in engineering for five years paying down my dues, find out if I made the career goal I wanted (you know, that one they ask you fresh out of college in interviews: Where do you see yourself in five years?), and get on with buying income properties where people would rent from me. But, nope. As one of my great college professors said my freshman year, "Make a plan, and plan on the plan failing."

So I left.  For about a year before then, I worked part-time outside of my regular work hours as a professional cuddler, and I started my own practice so I could at least hold myself over.

That was in February 2017. I had calculated that I had about 4 months worth of savings and during that time could make 3 months more worth of money before I'd start to have a problem with money, so the plan was to at least make enough to hold me over in survival mode until September which would buy me enough time for my lifestyle to go back.

Unfortunately, life happened. And also, human error. Here's some of the life and human error that happened:

1. I tried to maintain my eating-out lifestyle for the first two months.  This was a decent setback. I was used to not do cooking that much, and I socialized with my friends by eating out. I thought I was scaling back once I worked for myself, but my bank statements said otherwise... and I only checked them once it was too late. Whoops. My food bill was much higher due to eating out. Shortly after discovering, I started cooking a bit more often and letting my partner know that I couldn't go out to eat with him (to which he'd usually cover me if he really didn't want to cook).

2. My health insurance got more expensive. When I switched to state, tax-subsidized health insurance, I wasn't making my engineering salary anymore.  For about four months I was paying the tax-subsidized rate, and then suddenly the department decided I didn't have enough proof that I wasn't making my previous year's salary anymore and took away all my tax credits. I suddenly was paying $200 more per month for the same health insurance I had.

3. I got into a car accident that was I was at fault for. This not only raised my car insurance premium, but it also meant I had to pay the deductible to repair it. I didn't have the money then (because I didn't re-evaluate my deductibles for my car after I left my job), so I put it on my credit card thinking I would pay it off in a month or two.

4. Once I used my credit card once, why stop there? I got into the terrible habit of using my credit card to pay for things when I hadn't transferred money from my savings to my debit card, and I ended up overspending a lot (note: do not use credit cards as a substitute for savings. I know logically this makes sense and we're told not to do this all the time, but I'm reminding you again from my experience).

5. I didn't have an EZPass yet and I had quite a bit of pay-by-plate toll money and parking tickets to pay for. I have the bad tendency to put off those bills since they're not regularly recurring ones, so this did not bode well for me as you can imagine. The late fees on tolls and parking tickets are worse than the interest on credit cards.

6. June was a terrible month for my family full of long hospitalizations and funerals, and it wore on me mentally. I do not regret having been there for my family when they needed me, but it did wear me down to the point that I stopped taking on clients for most of the month because I didn't have the energy left to work. I made triple digits in my business that month, the lowest I made in any month that year.

By mid-July 2017, after I had come back from a planned trip in Portland Oregon, I not only had about $100 to my name, but I had two weeks to figure out how to find $1500.

Armed by a plethora of ideas, a near-to-ground-zero starting point, and my sheer determination to figure it out, I got cracking.  Somehow I managed to do it by the end of the month.

Here's the things that held me over:

1. I tried Lyft.  When I got super scared that I'd run out of my savings a few months prior, a friend of mine told me that when he and his wife were trying to get his book keeping business off the ground and making the income they wanted, they both drove for Lyft. I signed up through his referral link (this one is mine), and I got an extra couple of bucks as a bonus for each ride I gave during that time while he did.

Me being the engineering mind and busy entrepreneur I am, I tried to figure out how I could optimize how much I made for fewer hours. For where I lived and considering when I liked to work, doing the morning rush between 6am and 9:30am seemed most lucrative and I could easily pull in $100 every Monday and Friday morning (very, very helpful!). Not only that, but Lyft particularly offered bonuses for giving x amount of rides during certain times (usually because they needed more drivers during that time). So not only would I get surge pricing rates with my rides but I'd get a special bonus from Lyft, plus the temporary bonus money from Lyft for signing up through my friend's referral link.

On top of that, it was easy to just start working whenever I felt like it; if I needed money right away, I could just get in my car and turn the app on, and I lived near a college and could easily just sit in the car and wait. If I was driving to my boyfriend at the time's place in Central Square in Cambridge, I'd turn on the Lyft app and play what I called the "Lyft Game," which was simply start driving home from that very busy area of Cambridge after seeing him and see how many rides I could pick up in the five mile drive back to my place until I got about two streets away from my place. Sometimes I'd make $50 or more from doing that for an hour or two before I'd normally just drive home.

Looking back at that time period, I had managed to pull in $728 in that two week period that I needed to find $1500. That's right, I pulled in half the amount I needed to get from this time period.  How many hours did I work? 26 hours, forty minutes. That's about $27 an hour.

If you're an entrepreneur or a college student trying to make money this summer, I highly recommend looking into driving for a rideshare company. I personally can't talk about Uber and how good they are, but my experience with Lyft was very, very good for my needs.  By signing up through my referral link as of this writing, you can get an extra $2.75 per ride you give in your first 30 days, up to $550.

2. I tried doing grocery shopping or deliveries for Instacart. I'll admit, I didn't use this for the two weeks that I needed $1500 because I hadn't heard of them then, but I heard about them through a Lyft driver meetup.  Someone was asking about what others do when it gets slower for Lyft driving, and someone had put up their referral link for applying to Instacart (this one's my referral link). 

After I started to get tired of waking up at 6am to drive my car and keep it clean enough to take on passengers, I started trying out Instacart.  It paired well with Lyft actually; I'd sign up for hours with Instacart in advance so I knew when I'd be working, so I'd drive around the city for Lyft from 6am until around 9am, then my hours for Instacart would start and I'd get orders to go to area grocery stores to shop and/or deliver until my scheduled hours were done (I'd usually do 3-5 hours at a time with Instacart).

Some things to note: unlike Uber/Lyft, Instacart pays out once a week at the same scheduled time via direct deposit.  Also noteworthy: I noticed that I wouldn't make much money unless I had signed up for at least 12 hours a week (that's when it would range from 200-400+ dollars). That said, you could easily sign up for a 3-5 hours Instacarting each day on Saturday, Sunday, Monday and Tuesday and get a great haul. I recommend signing up for hours as soon as possible when they're available on Wednesday at 9am when hours are available (might vary depending on where you are).

You can sign up to do shopping and deliveries for Instacart through my referral link here.

3. I did some gigs.  Before I left for my trip I had helped a friend out with a last minute babysitting gig. They had liked me so much that they asked me to come back and help out twice a week for them when I came back. That was a solid $100/week right there for me, which instantly contributed to an extra $200 I needed for the $1500 challenging bind I was in.

Other places to look might be: Craigslist (it's much easier to find legitimate gigs listed on there now), Sitter City, the NextDoor app, or Facebook neighborhood groups. You can also post in these places that you're offering your services. Get creative.

Sidenote, some of these jobs can be more lucrative than you realize depending on where you are. When I was younger, dog walking and housecleaning for my neighbor's dog and her house paid for my driving lessons and my first used car within six months.

4. I worked my business. But more creatively and with more focus on tasks that mattered.

I don't think I worked harder during this period trying to make my business work in the evenings than during this period. This was actually how I invented the "Half Hour Coffee Talks" I now use for my business when meeting up with people.  At this point, it was mostly friends that were curious about what I've been up to or what my work consists of, but by trying this experiment I would meet up with them for select hours in the morning (when I wasn't Lyfting) and the weekends. The caveat? A $20 donation was appreciated but not required. Many people did end up giving me a donation (either as coffee or as the full $20), which to them may not have been a big deal but for me was just what I needed to make up the small difference in sales I didn't get.

By reaching out to leads and getting sales and doing these coffee talks, I managed to not only get the sales I needed at the time but I was also able to start getting bookings for next month. I started August 2017 with an overnight cuddle session scheduled, which meant my cashflow started high.

This whole period was insanely stressful and for months after (since you don't really recover right away after breaking even-- there's still more months and more recurring bills to pay). I was super appreciative for my then-boyfriends and my friends for supporting me how they could during that time. I made it work, but eventually, I began to slowly transition from my emergency gigs.

Why? Because they were just that: for an emergency.

My business didn't support me right away once I moved away from Lyft, Instacart, babysitting, or house cleaning... but I did notice that they took an awful lot of time and energy away from my business. And by the time I was done with my money-making gigs, I couldn't work on my business at full capacity.

Eventually (and with urging from my car insurance company which decided not to insure me for deliveries or Lyft), I transitioned away from all my little gigs and poured myself fully and completely into my business as much as possible.

It was terrifying.  And it still is sometimes. But I did it.

Because, like many that may be reading this that aren't sure yet how they're going to pay an insane number of bills, I figured it out.

I always do.