Allegra Stein

March 27, 2025 Reader, It’s really important that you hear this: It’s never too late to start looking at your money. It doesn’t matter how old you are. It doesn’t matter if your partner has always "handled the finances." It doesn’t matter if you haven’t opened your credit card statement in months. It doesn’t matter if you used to have a high-paying job and now you don’t (or the other way around). It doesn’t matter if you’re embarrassed by your Amazon order history. It doesn’t matter if you’ve...

March 26, 2025 Reader, Here’s the simplest way I think about budgeting: Make a plan for the money you have today. Stick it in envelopes to reflect that plan (I use a digital envelope system). Spend from your envelopes. That’s it. That's my approach. I know that “budgeting” means a lot of things to a lot of people. Some focus on tracking every dollar you’ve ever spent. Others are all about forecasting what you might earn and spend down the line. Those are all valid, just not the one I’m...

March 24, 2025 Reader, A colleague of mine - let’s call her Sara - is a freelancer who’s been helping a friend, Molly, update her website. They’ve worked together for years, and Molly pays Sara the same amount every month to keep things running. But this past February, Molly’s check bounced. Sara reached out, and Molly assured her she’d send the payment electronically. Rather than wait for the money to arrive, Sara went ahead and added it to her budget, assigning those dollars to her...

March 23, 2025 Reader, It's easy to think that if we’re not totally dialed in with our money, it means we’re doing something wrong or need to change right now. I hope that my energy and enthusiasm about all of this isn't fueling a sense of "should". If anything, I simply hope that how much I can geek out about this stuff leaves you a tiny bit more curious that you were before. Because sometimes, we’re managing so many other complex parts of life - relationships, work, health, caregiving -...

March 22, 2025 Reader, I want to be share more about what I mean when I talk about budgeting, because I know that word carries a lot of baggage. For a lot of people, budgeting means trying to predict the future:“I’ll earn this much, so I’ll spend this much.” Considered this way, it's not uncommon to wonder, “how can I budget if don’t know how much I'm going to make each month?” This is a very common question, especially if you're a soloist and run your own business. Most budgeting advice...

March 20, 2025 Reader, Talking about budgeting is sooo boring, amirite? Unless you’re me. I could geek out about this stuff all day. Do you know how giddy I get when someone sends me a question about spending, or YNAB, or how to plan their money toward a goal? (Seriously. Send me all the questions!) But I know I’m the exception. For a lot of people, “budgeting” lives in the same category as going to the dentist or watching paint dry (though you might love those things, too.) I know this might...

March 18, 2025 Reader, A couple of weeks ago, I invited you to get my daily Look at Your Money notes - quick thoughts about spending, cash flow, and what happens when we stop ignoring our money. Maybe you saw it and thought, “money stuff? No thanks.” And I totally get that! I know you’re here because of lots of different things I’ve shared over the years. Coaching, creativity, budgeting, who knows. My work has been a grand adventure, and I'm grateful that you’ve been along for the ride. And...

March 18, 2025 Reader, Someone asked me if they should block off a whole afternoon to set up their budget perfectly. There’s no set amount of time it should take. Every budgeting experience is different because your money, your priorities, and your choices are different. That’s actually why I don’t offer group YNAB setup sessions. It’s very personal and specific work. And honestly? The setup matters way less than what you do after. Your budget isn’t a one-time project. It’s a habit. A...

March 17, 2025 Reader, When your income is unpredictable, spending can feel totally chaotic and unstable. And if your purchases are tied to things you prioritize - your health, your family, your passions - it can be REALLY hard to say no. But without a plan and some intention, the chaos will persist. Before you make your next purchase, take a pause to consider: What still needs to be covered before more money comes in? If I buy this now, what won’t get funded? Is this a real priority, or just...