The Seasonal Strategy: A Shameless Approach to Pivoting

Embracing experimentation and releasing the pressure of permanence

This morning, as I browsed a neighborhood newsstand for magazines to add to my endless collection, I grabbed the ‘Fall 2024’ issue of a favorite publication of mine. Initially, the season that lined the spine didn’t catch my eye—after all, magazines are typically published by season. But yesterday, as I listened to this episode of the Spilling Tea podcast featuring Gillian Stevens, I was reminded yet again of this seasonal sentiment. And while I’m not particularly drawn to fashion, I was still intrigued by her story and the discussion regarding her seasonal wardrobe launches.

Seasonal launches and releases of new work have become the norm across such industries as editorial and fashion, but what about adopting such an approach to our careers and bodies of work?

The idea of embracing a portfolio career is one that has deeply intrigued me over the past year or so, especially as of late, following the writing and insights of others here on Substack (most of whom I’ve mentioned before like,

Anna Mackenzie

,

Cate Scott Campbell

, and

Jules Fedele

.) Portfolio careers give multi-passionate and multifaceted professionals the opportunity to incorporate several income streams, projects, jobs, and gigs into one career. As a previous start-up founder whose experience and passions lie across many categories, the portfolio career model allows me to “be more than one thing.” However, as I started paving my path towards building a portfolio career of my own, I noticed there were several blocks preventing me from moving forward. The most significant simply being to get started.

Logically, I know the only way forward is to put new work and ideas into the world before they feel ready. This is a lesson I’ve continuously learned during my two times co-founding tech start-ups: release before you’re ready, and don’t wait for perfection or else you’ll never release anything. In the tech world this looks like getting your product into the hands of users while there are still many bugs and issues to be resolved, even if it’s just an MVP that’s barely resemblant of the end-product you’re trying to build.

Again…logically, I know this to be true. But why, when I am now branching out on my own, outside of the structure of the start-up, can I not integrate this crucial insight? (I have a few theories that I won’t go into detail on now, but they include tying the entirety of my self-worth and identity to career, and fear of showing up and being seen. Deeper topics for another day!)

Having a background in branding, I thrive when I’m able to craft the perfect positioning, but when it comes to doing that for a personal brand, that’s a bit more challenging, isn’t it? Everything seems more personal now, like whatever work and offerings I put into the world need to perfectly represent the entirety of who I am and what I want to be known for. In simplest terms, it feels like pressure. Unrealistic pressure.

I’m someone that has been known to pivot…frequently. If you’re into human design, I am a manifesting generator through and through, hence my several business ventures over the past 8 years. After choosing to step away from our latest start-up due to having our second baby, I’ve had this fear to start over again, like the next thing needs to be THE thing, or else I’m going to have to pivot…again.

Seasonality is something I’ve given a lot of thought to, mainly in regard to how my career aligns with my personal season of life. However, it’s not something that I thought could inform the way I approach my career as a whole. But as I sat in silence while putting the baby down for his afternoon nap, this realization popped into my head that my career could indeed replicate the seasonality of a new magazine issue or fashion collection. That each season I could decide what offers, projects and ideas I want to be my body of work for that selective season.

Elements of a Seasonal Strategy:

Now bear with me, as I am thinking (well…writing) out loud here…

1. SETS THE EXPECTATION UPFRONT FOR PIVOTS, EXPERIMENTATION & EVOLUTION:

Maybe you’ve felt it too, the worry and shame around pivoting “yet again,” whether that looks like announcing another offer, starting another business or side hustle, working on a passion project, or something else. But with this approach, you’re setting the expectation of change upfront. Every season you get to decide what work you want to define it. And when the next one rolls around, you have the freedom to make edits and pivot as you see fit, without the shame. Why? Because pivoting is literally built into the model with each season presenting a new opportunity to shed what didn’t work and to move forward in the most aligned way possible.

2. TAKES AWAY THE PRESSURE OF PERMANENCE:

When we take this approach, everything we release into the world is naturally confined within the season (or seasons.) Therefore, long gone is the pressure for the next thing you do to be THE thing you do and are forever defined by.

3. GIVES STRUCTURE TO CHANGE:

When we think about the seasons of nature, in essence, what do they do? The way I see it, is that they give some much-needed structure to change. We know when the season is about the change and therefore can anticipate (and even become excited) for what the new season ahead will bring. By approaching our work in this way, it can give us the structure to know when we’re going to launch new ideas into the world, as well as let others in our network know when and what to expect.

4. NATURALLY CREATES URGENCY:

If you’ve launched something before, you’ve probably heard the need to “create urgency” in order to drive sales. This approach naturally incorporates urgency into your offerings or projects as you may, or may not, offer them again the following season.

5. PROVIDES ACCOUNTABILITY:

Over the past year or so, I’ve learned that I’m someone who needs some sort of accountability to remain consistent. Maybe you are too. This accountability could take many forms, like an “accountability partner,” a client that’s signed a contract, or something else. I feel like this seasonal strategy creates accountability for the months ahead, as it gives you (and your community) a clear vision of what the focus is.

6. OPPORTUNITY TO AUDIT:

After we’ve been in a certain position for awhile, whether it’s a job or a service we’ve been offering, we can get stuck doing the same thing everyday without questioning if it’s actually serving us or bringing us closer to our aligned goals. Approaching our bodies of work by the season creates the opportunity for pause, to audit where we’re at, and question where we want to go next.

7. A WAY TO BUILD YOUR PORTFOLIO CAREER:

I see this as a strategy to building your portfolio career, especially as it prioritizes evolution and making space for multiple projects. Whether you’re at the beginning of developing your portfolio or are in the phases of evolving what you want your career to look like, embracing seasonality can give you the space to experiment and see what sticks.

Putting This Into Practice:

I’m currently finalizing what I want the rest of my “Fall 2024” and upcoming “Winter 2024” to look like. Personally, I’m not only including income streams, but also personal projects I’m working on, like this Substack. This way I have a clear vision for where I’m investing my time and energy this season, and can let others know as well:

1. SUBSTACK & INSTAGRAM: I’ve taken a personal vow to put myself out there more and to prioritize community growth for the next several seasons. To me, this means showing up consistently on Substack (and Instagram) where I feel I can connect with my most aligned network. Realistically I know this will be a big undertaking, but in the long-term, I know this will only get me closer to my vision, even if it requires going outside of my comfort zone and working through some fears of being seen.

   

   a Substack note from earlier this week

2. SERVICE OFFERINGS: Services are the main reason why I wanted to adopt this “seasonal strategy” in the first place. As this is the first time I will be formally offering services as an independent person, I want to give myself the opportunity to experiment and try things out, whether it be what I’m offering, clients I’m working with, etc.

So, in summary, my Fall 2024 will look like publishing to Substack weekly, as well as experimenting with new service offerings. Maybe these offerings will continue into subsequent seasons, or maybe I’ll move into the next season with something different. If you also identify as a multi-hyphenate or multi-passionate, I’d love to hear your thoughts on this strategy. Is it something you’d try out?

As always, thank you for being here.

Until next week,

---