Don’t make the same mistakes I did. Speed up the growth process by using tools designed for a strong foundation early!
I get asked all the time what I would do differently if I had to do it all over again. To that I say: marry for money and retire on the French Riviera at 25.
Though, if we’re talking about smart choices within my field I have some things I’d do slightly differently. It took me trial and error to arrive to the four that stand out the strongest. While I think much of it was a learning curve I needed; had I just trusted the process and been given these options early on I am sure I would have found greater success. I also would have saved heaps of money in IRS debt, made more money and had more time for clients.
I would have gotten a corporate card first

Not a business card but a card specific for my business expenses. I would have opened a credit card specifically for any regular expenses I was incurring much sooner. I realized much later just how annoying it was have toileting review multiple statements in order to reconcile my expenses at the end of the year. In addition to the hassle, came the loss of rewards. I would have saved thousands in my first year by maximizing the perks and cash back on my cards. I found myself making bill payments with debit cards, earning no points back and certainly not building my credit. Having a smaller, separate card for business not only builds credit but can offer incredible rewards. Cards like the Sapphire Reserve card from Chase offer great percentages back on many of the brands we use most often in the industry. If you’re using systems like QuickBooks or shopping primarily at Staples for your supplies, find out which cards will offer you the most bang for your buck. I cringe to think of how much money I could have saved in gas alone during my genesis.
I would have started using Airtable right away

I know I evangelize Airtable all the time but it’s truly because I love their product. When I first starting using it, It was to keep my direct contracts easily accessible and sorted. I quickly made it the only solution I used across the board.
As a freelancer I use Airtable to
- Track my gigs and keep them sorted by date, client, rate etc…
- Automatically add gig information to my Google calendar, complete with updates, reminders and notifications. Daily reminders? Morning briefings? A single click!
- Keep client information organized
- Manage communications with clients along with a running log of notes for each interaction
- This allows me to quickly reference information they’ve given me before the same way a phone rep can pull up account notes
- Upload, organize and schedule my prep work and time
- Keep track of my invoicing
- Sending my invoices
- Track the payments I’ve received
- Calculate and track payments to the IRS
- Calculate deductions needed for monthly bills, health insurance and retirement
- Track my expenses
- To balance all of my finances from start to finish
- See all of my income
I now use Airtable every time I teach. Not only was it a game changer for me but it’s helped so many of my colleagues find more efficiency and organization in their own practice. It’s become such a hot service for my clients that I developed a customizable freelancing template for purchase.
I would have started using Google Calendar

While I’ve always been a pen and paper kind of guy, I love technology. I genuinely believe it improves our lives. Yet, I was still very late to the cloud calendar game. My hesitancy came after losing my entire planner in a cloud migration which left me missing jobs and double booking the few that still appeared on the app. Now, I use google calendar regularly. I can’t lie, the paper backup still exists in my bag all full of notes and receipts. I don’t need to refer to it often and now I primarily use it as a record should I need to go years back and refer to a job I did.
As an aside, I would have started using Google Drive to host my portfolio as well. It’s not my favorite resource but simpler than most others.
I would have bought a Moleskine notebook the day I started working

I tell everyone I work with, get a notebook. NOW! As a business, you have a ton to keep track of. You’ll have conversations with clients before writing a contract, specific emails to write down for sending invoices, to-do lists a mile long. If you’re not intentional about getting it down on paper, it will get away from you and fast. Along with the day to day stuff, you have ideas and stresses. Having a place to pour those into can be the difference between falling behind and maintaining a manageable practice. I personally hate being distracted in the chair, so I keep my notebook close by and if something needs my attention urgently, I jot it down for later.
I wish I could tell you how many times I’ve woken up in the night in a cold sweat thinking I forgot to invoice a client but at this point I have lost count. When those things happen, I write it in the notebook and wake up to it. This way, I can handle urgent matters in the morning when I am more rested, have had some coffee and am thinking clearly.