Welcome Back! And On Paying Yourself First with Your Time

You’ve been a subscriber of my newsletter in the past. And now, I’m back, but this time on Substack. I still write at When I Have Time, and much less frequently on Ms. Adventures in Italy (my archives are still available), but here I’m going to continue delving into topics I explored on my newsletter, a newsletter which is now over 10 years old - my first issue was sent in February 2012! If you’ve been here this whole time, thank you 😊

I’m going to talk about being a human at work, home, and in the world - so continuing to dive deeper into technology and business, this remote work thing which is definitely sticking around (I’m 12+ years and counting working remotely), leadership and mentoring (currently Director of PMM at HubSpot), and into a longer tail of topics like anti-racism, productivity, writing, product management/marketing, self-improvement, personal finance, motherhood, and health.

One of the most inspirational and giving leaders Deb Liu (subscribe to her Substack here) said about her own newsletter - “Does anyone even care about what I have to say?” - if she feels that way, I can assure you that I feel that way 1000x, even if there are thousands of you who have subscribed over the years. I am choosing to go back to why I started most of my online publishing in the first place (and the main purpose of When I Have Time): to help at least one more person by publishing topics and perspectives from my 1:1 mentoring, conversations with friends, and private consulting.

I will always publish some free content, though in the future I may decide to offer some additional content or benefits for a paid tier.

First, some housekeeping - in case it’s not clear, I believe: Black lives matter. Trans lives matter. Science is real. No human is illegal. Feminism is for everyone. Kindness is everything. Abundance over scarcity. Love over hate.

Now let’s get to it. As Lizzo says, How you feeling?

Paying Myself First with My Time

My coach Dani recommended a book to me - Four Thousand Weeks - Time Management for Mortals (affiliate link), and though I’m not all the way finished yet, it’s already had an impact on me.

How am I paying myself first with my time?

The concept of paying yourself first, which originated in the personal finance world and is about automating savings and investing so that you’re making progress towards long-term goals first instead of after your other expenses come out of your paycheck. The logic is by making these choices first, and ideally automating them, you’ve committed to making progress against your financial goals and it’s not a choice you re-decide with every paycheck or after paying the month’s expenses, when your willpower (or bank balance) may be weaker.

It’s a super simple concept that many can understand when it comes to money (and I do this myself with my finances), so when O. Burkeman recommended applying the concept of paying ourselves to how we live our lives and think of our time, a huge lightbulb went off:

Thinking in terms of “paying yourself first” transforms these one-off tips into a philosophy of life, at the core of which lies this simple insight: if you plan to spend some of your four thousand weeks doing what matters most to you, then at some point you’re just going to have to start doing it.

What matters most to you? Are you doing it? Do you pay yourself first or do you fit it into the empty spaces left over after everything else has taken your time?

What does paying myself first look like right now?

When I embraced this concept of self-investment and stepped away from the more widely touted self-care we’re all trying to do right now, it became clear to me that part of my mental health didn’t want further distractions, or even relaxation.

For me, it was realizing that one of the ways I need to keep investing in myself is to make space for and prioritize being in a generative mode vs. consumptive. While I’m often in generative mode at my day job, and in busy mom mode as a mother to two young children, I realized that a purely consumptive mode (reading or watching) in the unclaimed time left over was leaving me feeling a little hollow. On the surface those are relaxing activities, but relaxing wasn’t all that I needed.

Creating and generating for myself is energizing. Thus the return to paying myself first, and investing in myself. And this newsletter.

We’ve come full circle.

How to get started with paying yourself first

What could paying yourself first look like for you? Besides reading the book (which I recommend), here are a few tips to get you in the mindset:

Since this is super personal, try to center reflecting on your goals, dreams, and hopes for your life as the foundation for investments you need to start making in yourself.

• It helps to journal or write them down when you start this, so you have clear ideas in front of you to consider.

• Think about the longer-term dreams for yourself, those wishes, those hopes, those “I could nevers” or “I’ll do it whens...”

• Think about what kinds of activities, work, or exploration energizes you.

• I do a yearly planning exercise (the template and method are on When I Have Time) and the macro categories for myself are: health, relationships, wealth/financial, and career.

Start small - pick one area / topic / goal to start investing in yourself and paying yourself first.

Open that calendar of yours.

• What’s urgent? What’s important? What’s just being busy? What’s a distraction? Is there something which isn’t as urgent or as important which could be delayed or ignored? Is there something you could stop doing next week to free up some time?

• Starting with next week, put some time on your calendar as something other things must work around. Run calendar defense on that time slot - if it needs to move, something else needs to fall off.

• If you can, make that time recurring each week, or spend some time at the end of the week setting up the following week.

• If you don’t have a plan for what you’ll do during that time, don’t worry and don’t let that get you nervous. That’s why you’re making the time, to start making that investment in yourself. Just show up.

Try it and let me know!

I appreciate you reading along. If you’d like to say hello, suggest something for me to muse on/answer next - fill out this form, or just click that heart if you enjoyed this, I appreciate it!

Bonus Pro Tip - Did you know you could see all your Kindle highlights in one place, on https://read.amazon.com/notebook ?