How Much Should We Be Planning?: April 2, 2018 Monday Money Check-in

I didn’t know about this thing called “planning” for about the first 25 years of my life. I’m definitely learning to love it. It’s like, Ooh, you mean I can plan for the future instead of letting it bat me in the face with consequences when it finally arrives? Tell me more. 

This year, I put up a laminated year calendar on the wall of the office I share, and it’s given me such a sense of control. I don’t write on it in permanent market, so if I need to change my plan, I just lick my finger and wipe off what I thought would happen, write in what will actually happen, no big deal. I think before I was scared that if I didn’t get it exactly right, I’d be screwed.

As Michael Gerber has said, “Businesses that plan always do better than businesses that don’t. But businesses that change their plans are always more successful than businesses that plan but don’t change them.”

So you have to find that happy medium. I started the earliest version of this blog with a weekly check-in. I’ve added a monthly and a yearly, but today I realized it’s the start of Q2, so I’m going to do a quarterly one too.

Am I allowed to use phrases like Q2, if I’m a creative freelancer? Yes, because you are also a business person. Everyone is a business person, even an employee. A person is a business. We all want to stay in business. This is especially true of freelancers.

Planning takes time. I spend almost all of my Monday planning, doing my executive meeting and this check-in. But it’s time well spent. Invested.


I’m not doing that well with money right now guys, and I forgive myself. I’m going to keep working hard. I’m going to zoom out to the year, the quarter, and not let myself get lost in the little failures. I’m laying a lot of foundations for things that I trust will pay off later. But I have to save my fuck off fund this year, and I cannot make myself financially desperate while I’m networking and going to conferences.


  • Earned last week: $839. Short of my $1,000 goal. And I need to make some serious money because I have two conferences coming up this month, one in San Francisco, the other in New York City. Not cheap places. 
  • Saved last week: $0
  • Personal Checking Balance: $0
  • Business Checking Balance: $3
  • Fuck Off Fund Level: $2,000
  • Weekly wins: I did not do well last week guys. Like, seriously, a musical montage of everything freelancers could do wrong. What did I do right? There must be something… hmmm. Oh! When I was on Nicole Dieker’s podcast and I asked her why her voice is so clear and amazing, she told me she took voice lessons. So I signed up for voice lessons!
  • Look at all bills due this week: Rent, health insurance..
  • Update and review budget (I’m changing to YNAB): Done. I’m really learning that YNAB makes you see where you’re stealing from yourself. 
  • Look at any social events where I might want to spend some of my Fun Money: Thank god, I think I can keep it really low-key. 
  • Transfer 10% of money received last week: Easy, didn’t make any
  • Transfer $200 to Fuck Off Fund: I’m not going to do this right now, but I have a $400 payment coming in I can do it with. 
  • Transfer 20% of earnings to Tax Savings Account: Don’t need to. 


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