September Is My New Year. Here Is How I Am Setting Goals Differently This Time

I have always treated September as my real new year. Not January. September.

Part of it is the school season, that distinct shift in air and energy that arrives every fall, regardless of whether you have children in your house. Part of it is that my birthday falls in September, so there is already a built-in moment of reflection. And this year, I was reminded that Rosh Hashanah, the Jewish new year, also arrives in September, bringing with it its own tradition of renewal, intention, and beginning again. Multiple calendars pointing at the same thing. It felt like a sign.

It got me thinking about what goal-setting looks like in this particular season. And I realized: it looks different than it ever has before.

The Framework That Served Me. And the One That Serves Me Now.

For most of my adult life, I have been a SMART goals person. Specific. Measurable. Achievable. Realistic. Time-bound. That structure has served me enormously well. When I was scaling Basil Financial Group with my mom, SMART goals were exactly the framework we needed for that season we were in. The destination was clear, the milestones were trackable, and having that precision gave us both something concrete to build toward. There is real power in knowing exactly where you are going.

What I have discovered is that different seasons of life call for different frameworks. And the season I am in now, launching two businesses, raising two children, rebuilding a professional network and finding my true voice, is calling for something different.

Career coach Megan Hellerer describes it in her book Directional Living: A Transformational Guide to Fulfillment in Work and Life as the difference between destinational and directional living. Destinational living is the SMART goal world. You pick a fixed target, you work backwards, you execute. Directional living is something else entirely. It is about identifying the direction that feels true and letting the specific destination emerge as you move.

Hellerer argues that the traditional goal-setting model has created a generation of what she calls Underfulfilled Overachievers: people who did everything right, hit every goal, arrived at the destination, and found themselves burned out and empty. I recognized myself in that description. And I recognize a lot of my clients and friends in it, too.

What Directional Looks Like In Practice

In late June, I left my role at a large national wealth management firm after a season that, while professionally productive, did not match my values or the clients I most wanted to serve. 

In early July, I launched as an independent financial planner through Savvy, alongside a coaching and education brand called Ambitious and Aligned. Two businesses, one vision, a completely blank canvas.

In an ideal world, I would have written down exactly how many clients I want by December 31st, how many events I want to host, how many followers I want on Instagram. And while some of those numbers will matter eventually, right now, sitting in the middle of a major transition with two children under five and a brand new business, the most honest thing I can tell you is: I do not know yet. And I am giving myself permission not to know.

What I do know is the direction. I want to feel energized by my work more often than I feel frantic or depleted. I want to be serving clients who genuinely need what I offer. I want my calendar to leave room for the things outside of work that make the work sustainable: my health, my marriage, my friendships, my community.

The first weeks of building were instructive. During one particularly wild stretch, I scheduled four prospective client meetings across two days, layered on top of daycare drop-offs, camp pick-ups, touring my new office space and the everyday logistics of family life with two young children. Some of those meetings were at coworking spaces I had not fully settled into yet, none of them close to home. By the end of the week, I was frenetic and tired. Not energized. That feeling is data. Directional living means you pay attention to it.

The Weekly Energy Check

One of the practical tools I have brought into this season is a simple end-of-week energy audit. Three questions I ask myself on Friday afternoon:

1. Did this week feel manageable?
2. Was I energized, depleted, or frenetic?
3. Did I protect my buffer time? (The unscheduled, strategic thinking space, that I know I need to do my best work)

That last one comes from something I learned while building Basil Financial Group. The weeks that felt most productive were rarely the ones that were most packed. They were the ones that had room to breathe.

For the physical organization piece, I have been using the Ink and Volt dashboard planner, which has a flexible format built around identifying your top three priorities, your big rocks by topic or day. If you are not familiar with the big rocks framework, it comes from a classic time management illustration that makes a simple but essential point: if you fill your jar with sand first, the rocks will never fit. Start with what matters most. The small stuff works around it.

What This Means for Financial Planning

Here is where my work with clients comes in. I have spent eleven years watching people set SMART financial goals. Retirement by a certain age, a certain amount in their investment accounts, or a house at a certain price point. Sometimes people hit all of them while still feeling financially anxious and unclear about what they actually want.

Directional financial planning asks different questions. Not just what is your target retirement age, but what does a day in your life at 67 actually look like? Not just what is your savings rate, but does your current spending reflect the life you say you want to be living? Not just what are your assets worth today, but are you moving in a direction that stays true to your values, or have you been optimizing for a destination someone else set for you?

The financial plan that holds up over time is not the one built around the most precise projections. It is the one built around a clear and honest understanding of what you are actually trying to build and why. The numbers follow from that clarity. The clarity does not emerge from the numbers.

Wherever You Are This September

If you are in a season where SMART goals are working beautifully for you, where the destination is clear, and the structure is energizing, lean into that fully. That clarity is something to honor, not something to move away from.

But if you are someone who finds themselves in a season of transition, a new role, a new business, a new chapter after a life change, I want to offer you permission to be directional instead.

Ask yourself how you want to feel. Notice when you feel frantic and when you feel energized. Protect your buffer time; it gives you much-needed margin. Let the specific goals emerge from the direction rather than forcing the direction to serve the goals.

September is a new year. You do not have to have it all figured out to begin again.

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