On our drive from Positano to Siena, we decided to stop in Civita di Bagnoregio, which turned out to be an excellent decision. The 2500 year-old city is only accessible by foot, via a steep pathway and is one of the most unique places I’ve ever visited. Taken 7/18/16.
We almost skipped riding up the chairlift on Monte Solaro in Anacapri, but I’m so glad we didn’t! The view was absolutely incredible and was one of the highlights of our two-week honeymoon in Italy. Taken 7/14/16.
Even after living in Philly for almost 4 years, I had never made it out to The Wissahickon Gorge. It was a beautiful afternoon yesterday, and I jumped on the opportunity to do some exploring along Forbidden Drive.
It ended up being a perfect way to spend a few hours: the sun was out, the air was clean, and I had a great time walking around with my camera, snapping photos of everything. Sometimes it’s easy to forget just how green the world is when you’re living in a city.
Roughly a year ago, I decided to give churning credit cards a try. If you’re not familiar, churning is the process of signing up for credit card offers, primarily for their potentially lucrative sign up bonuses and doing it over and over again. There are entire sites and forums dedicated to it, so there was a lot to learn.
In total, I ended up signing up for 6 separate credit cards, earning roughly 300,000 points/miles from the bonuses alone. With those points, I’ve been able to take 3 domestic trips already (with 2 people each time) and I was able to book our upcoming honeymoon to Italy, as well as some other trips, with points left to spare. I’ll also soon have a Southwest Companion Pass, which I’m pretty excited about.
It’s been a fun and also slightly annoying process, so I wanted to put together a quick post with my thoughts.
Keeping track isn’t hard, but it is annoying
In total, I have 9 credit cards currently open, which sounds like an enormous pain to manage, but it actually hasn’t been too bad. Everything is set to automatically pay the balance in full every month, and I use Personal Capital to keep track of all of the transactions in one place. I also am only ever using one card at a time, so it’s not as bad as it sounds.
While it isn’t difficult to manage, it can be annoying. Instead of one or two credit card payments a month, I have 9 to keep track of, all on different dates, which can make it difficult to know when money is being transferred. A lot of the cards also have an annual fee, which I need to stay on top of, so I’m not accidentally paying for another year, when I don’t need it any more. Creating a Trello board and adding reminders has helped me keep everything in one place.
There’s also the drudgery of switching over monthly bills every time I get a new credit card. In order to meet minimum spend requirements, I try to move as many bills as possible to a new card, which requires logging into every subscription or utility site and updating my billing info. Again, nothing that’s difficult, it just takes time.
I should’ve planned out my travel a bit more
When I first started signing up for credit cards, I didn’t have a specific goal in mind—I just started with US Airways/American Airlines cards, because Philadelphia, my home airport, is a pretty big hub for them. However, it turns out that a lot of my travel recently has been Southwest, and I would’ve been better off focusing on them, rather than AA. Instead, I now have around 100k AA points sitting in my account that I don’t really have a plan for, and I’ve been using Southwest points constantly.
Rather than just stockpiling points just because I could, I should’ve sat down and looked at where I was planning to travel and what it would take to get me there.
It’s hard to beat flying for free
Okay, maybe not completely free, when you factor in the time and annual fees I’ve paid, but being able to book a ski trip on a whim with points is really great. Southwest, in particular, has been amazing for redeeming miles—they fly to a lot of places out of Philadelphia, and it’s very easy to find and book flights. Also, I should be getting a Companion Pass in the next month or so, which will allow my fiancée to fly everywhere I do, completely free. Amazing.
Worrying about credit score is overrated
A lot of people will tell you that signing up for credit cards is horrible for your credit score, but I really haven’t seen much of an effect. Your mileage of course may vary, but I still have roughly the same score as I had before, maybe even higher. Now, if I were planning on taking out a large loan any time soon (like a mortgage), I’d definitely need to worry about this more, but for now, it’s not an issue.
I’m probably going to slow down for a while
As I mentioned, I’m currently working on getting a Southwest Companion Pass, which I should have in the next month, but after that, I’m going to stop signing up for new cards for a bit. It’s just too much of a pain to bounce between different cards, and I should have plenty of points and miles to cover my travel for the next year or so. I’ll just stick to my trusty Chase Sapphire Preferred card and cancel (or downgrade) the rest.
That being said, I really want to fly international business or first class sometime, and that’ll require earning more miles, so I’ll probably be diving back in soon.
Just a few days ago, I passed the 1 year mark of freelancing, and I thought it’d be a good opportunity to look back at the year and share some thoughts. So, without any further ado, and in no particular order, here’s what I’ve learned so far.
Find clients and then quit
I knew I wanted to give freelancing a try long before I quit my job, and because of this, I was able to bootstrap my business while still earning a regular salary. I highly recommend this. Instead of quitting your job and then trying to figure everything out, start doing it while you’re employed and you don’t have to worry about where your next paycheck is coming from.
By the time I quit my job, I had incorporated my company, found my first clients, and I had been freelancing on the side for a couple months. The extra income I earned on the side gave me the financial cushion I needed to make the switch, and on the day I quit, I knew I was going to have money coming in, from the clients I had already lined up.
Pay yourself a salary
One of the best decisions I made when I started was to pay myself a salary each month. I decided on a set amount, and wrote myself a check every month on the 1st, just like I was at a real job. Even if the company makes 2x my “salary” in a month, I still pay myself the exact same amount.
Since I was happy with what I was being paid at my previous job, any extra money the business earns just builds up as a savings buffer in its bank account, giving me peace of mind. It also is a great way to enforce the difference between business and personal money.
Freelancing is a business, treat it like one
Along the same lines as my salary point, it’s really important to realize that freelancing is a business, and you should treat it as one, even if it’s just you. This means having a separate business bank account, hiring an accountant and a lawyer, and keeping track of profit, expenses, and more.
It’s also important to have time to work on your business, rather than in it. You might be making loads of money, because you’re billing every hour to clients, but you’re leaving no time to plan out your business, which is really important. Once your current client work ends, you won’t have anything in your sales pipeline, since you haven’t had any time to focus on it.
This, in particular, is something I am trying to improve on—too often I’m heads down, working on client projects, when I should be reserving some time every week to work on the business.
One of the most enjoyable parts of freelancing has been everything I’ve had to learn on the business side of things. While I’ve been developing software for a while now, I had basically zero experience running a business until last year. In particular, the following books were, and continue to be, incredibly helpful:
- Working for Yourself: Law & Taxes for Independent Contractors, Freelancers & Consultants: This is an awesome reference on the legal side of freelancing. In particular, the section on contracts was super helpful.
- Double Your Freelancing Rate: Pretty much anything Brennan Dunn puts out is gold. Even if you’re just starting and don’t yet have a freelancing rate to double, this is a great read on selling yourself as a high value freelancer. If you don’t want to buy DYFR yet, check out his free course on pricing.
- The Positioning Manual for Technical Firms: Lots of great advice on how to position yourself as an expert
- The Brain Audit: I’m still working on putting what I learned from this book into practice, but it was a great read on why people buy, and how to attract exactly the type of clients you want.
- The E-Myth Revisted: A classic book on building a business that can scale, using systems. The main takeaway from this book is what I mentioned above: work on your business, not in it.
I also went to a few conferences this year, and the one that I’m still thinking about is PeersConf. I learned so much just by talking to other freelancers and agency owners, and all of the talks were phenomenal. I can’t wait to go again next year.
It’s not as complicated as you think
There’s certainly been a lot to learn since starting out on my own, and when I started, I was worried I wouldn’t be able to figure it all out. From sales to legal issues, it all seemed super overwhelming. Looking back now, it really wasn’t so bad. Sure, it hasn’t necessarily been easy, but it’s certainly not impossible. Once you get started, you’re always learning and always getting better.
For instance, having to do sales probably scares a lot of people away from going out on their own, but at the end of the day, it’s not like you have to be Steve Jobs to land a client or two. You just have to be willing to talk to a lot of potential clients and try to learn something from every interaction you have. As long as you keep learning and improving, you’ll get there, and that’s coming from someone who still has a lot of learning still to do!
Benefits are just money
A common concern potential freelancers share is losing all the benefits of a full-time job: health insurance, 401k matching, paid vacation, and more. At the end of the day, these are really just money. Sure, once you’re out on your own, you’re going to be paying for health insurance yourself, and there won’t be a company matching your 401k contributions, but if you’re not making enough to cover these benefits, you’re not charging enough.
In some ways, figuring out your own benefits can lead to saving money as well—if you want to, you can elect to pick health insurance with a high deductible, to save on monthly premiums. And, for retirement savings, you actually have the ability to save way more money with something like an Individual 401k or a SEP IRA than the typical company plan.
Goals for next year
My #1 goal for next year is to really nail down a sales strategy/pipeline. I’ve had the luxury of finding some longer term clients, which has made me lazy on the sales side of things, but that won’t last forever. Building a consulting company that I can run for the next 20 years won’t happen unless I figure this out.
After that, I’m hoping to start experimenting with working with subcontractors, to be able to take on larger projects and not have everything depend solely on me. Down the line, I can definitely see myself hiring employees, so testing the waters by subcontracting some work out feels like a good place to start.