The Season that Never Actually Ends (Sadly)

There is a moment in the calendar always waiting for. It does not have a name, but you know exactly when it is supposed to arrive (SUPPOSED to). It is the period of time after the current crunch, when the deadlines clear, the calendar finally opens up, and you can lift your head and think about the bigger things. You can pick up your dry cleaning (if we still do that), get your haircut, and make that dentist appointment. It’s also the time for focusing on growth initiatives, relationships, networking, events, training… and all the other stuff that was on hold.

Everyone in this profession knows that busy season feeling, and that post-busy season anticipation. 

But alas, our world is changing, or rather, has permanently changed. Busy season ends and the work does not. The client work that consumed you is replaced by different deliverables and reporting, planning, billing, recruiting, training, board meetings, events, reforecasting and budgeting, estimates, performance evaluations, and more. For a lot of firms, this means June is NOT a slow month at all. It could even mark the end of the end or beginning of the firm’s fiscal year. The “off-season” is just a differently shaped busy season. The pressure changes its costume, but it does not leave.

So the leisurely time do those nice-to-have, strategic things keeps getting moved to the next opening in the schedule.  Which never comes. And the advice you hear does not help, because most of it assumes that an opening does indeed exist. 

• Time for reflection and self-care. 

• Block off Friday afternoons for focus time. 

• Carving out a week or two for business development. 

• Take the team to an offsite and team-building meal. 

The advice is fine in principle, but it assumes a kind of margin in your calendar most leaders simply do not have, in any season. Period.

The Real Question Is Not Whether You’re Doing It Right

Here’s where most leaders get lost in shoulding on themselves. They often have some version of, “If I were more organized, I should have time for all this stuff.” That secondary or even tertiary pressure is NOT helpful. Instead, let’s try something different. 

Start by asking if what you’re doing is actually working. Not in the abstract. Is any of this busy season/non-busy season distinction working for you, for your team, for your firm.  For your family. For the practice you are trying to build. Each of these spheres has a different place in a leader’s cost-benefit analysis. I have never seen any two leaders ask these questions in the same way.

For example, a way of working can be productive for the business and quietly expensive for the family. Certain OKRs and KPIs can look fine on the utilization reports and feel like needless erosion to the people on your team who keep waiting for the version of the job they were promised. An operational framework can be working for one quarter and working against the business over the next two years. The point is not to feel bad about any of that. The point is to intentionally look, because most of us never do, or maybe we don’t feel like we can. But the best leaders I work with look at this type of audit as a must, a need to have.  This kind of calibration is not a nice-to-have.  It IS the job. It’s not enough to just keep moving, season to season, and assume the arrangement is fine. 

So if we are to consider reframing our world against reality, is the distinction between “busy season” and “non-busy season” really effective?  (Spoiler: I don’t think so.) 

The Ground Is Moving Under All of It

There is another reason this is worth looking at now, and it has nothing to do with how hard you work. The shape of the work itself is changing. Whole-dataset auditing is replacing sampling, which means the parts of the job that used to absorb the season are starting to compress. Real-time compliance is pulling work out of the discrete chronological windows it used to live in. And there is an AI-powered value proposition forming underneath the entire profession that, to be honest, no one has fully figured out yet (including the firms moving fastest on it).

None of that means the “busy season” disappears. It probably won’t. But it does mean what we used to call the busy season will look different from it has in the past. And the most thoughtful leaders I know are taking advantage of this golden opportunity to think through the ROI of energy management, not just time management. They’re looking at team composition, skills and capacities into the future, not just what is needed right now. They are looking at how to maintain their health, wellbeing, AND performance year-round, not just for a few months out of the year.  They’re having conversations with clients and prospects and referral sources about what really matters, where the value proposition is shifting to.

When the technical work compresses, the thing that differentiates you is no longer how well you executed the close. The machines are going to be very good at the close. What is left is the relationship. The judgment. The conversation a client cannot get from a dashboard. The trust that took years to build and cannot be automated. That is not a soft skill anymore. In the profession that is coming, it is the value proposition.

This also means the way you have been thinking about business development, as the thing you will get to once the season clears, must change. 

Where to Start 

I am not going to hand you a system here, because the shift is not procedural. It is a mindset and a way of working (like a way of being). It shows up in small moments and practices that add up, rather than in a calendar block or single month of the year. This is why it looks so insignificant, and what also makes it devastatingly challenging. 

• Mindfulness and Meditation. The more I learn about this area of leadership, the more essential and central it becomes. This is NOT about meditating religiously every day, but about a fundamental reconstruction of how you interact with the world, with others, and with yourself. I’d recommend a friend and colleague of mine, Timothy Swords of Mindful Executive Leadership Coaching for more on this specific topic and its centrality to sustainable leadership.

• Outsource More. Even the best of us hold onto too much. I find myself doing this from time to time, and I see my clients do it, too. It’s uncomfortable to choose to trust and train someone and hand something over. It’s hard to face the fact that you can’t think through the problem on your own. But it’s the only way to advance, and in some cases, survive. If you’re hoarding a task because only you can do it “right,” I think that’s something to question deeply. There may be something very off about that thought process; you might be trapped in a fixed mindset vs. a growth mindset.

• Isolate More Strategically What Only You Can Do. (This is kind of a continuation of the previous point.) I play these silly mobile games where you run around defending a castle or running a restaurant and stuff. The key to winning those games is about hyperfocusing on what things ONLY you can do at each stage. That changes over time. Like in the beginning, you’re chopping wood or frying chicken burgers until you can hire someone. Once you hire someone, they’re slow, and you might be tempted to do it quicker than them. But that’s the trap! It’s not about their speed; it’s about doing what only you can do as a leader. You not only need to outsource, but you also need to recommit to your actual job description as a leader.

• Give Up Self-Care for Executive Performance Management. I hear a lot about self-care, and I think it’s a good thing. But I want to push that idea further. Self-care can sound like something for the privileged, maybe it even sounds indulgent. But if we talk about Executive Performance Management instead, and reframe self-care as the fuel for your vehicle instead of the tune-up or upgrade, we might treat our wellbeing differently. I know I have when I started thinking about things this way! It’s been a game-changer. Things I thought were nice-to-haves are now need-to-haves, and I feel more productive and balanced because of it.

Assume the Worst

(This sounds funny or counterintuitive, but hear me out.)

Let’s play a mind game where that “slow time” never comes. Instead, assume there will always be some big, complicated, hairy thing happening in your world. Maybe the friction comes from your personal life, maybe from your work life, maybe from somewhere else. But let’s assume that life isn’t ever really easy or simple or abundant. Or maybe you feel this is your reality right now! My question is a bit challenging: Why do you still think that you’ll get to your list of important-but-not-urgent things when you “have more time?” 

Really? Because there are likely things that have been on your list for a really long time. The intentions are good, but if they don’t get addressed by you, handed off to someone else, or taken off your list altogether, they’re nothing more than nice ideas.By contrast, the most strategic people I know never wait. Instead, they make plans. They make appointments. They anticipate disruption and run backup plans and scenarios. They build people and systems and habits they can rely on and fall back on. They also regularly remove things from their lists when they don’t serve. They keep their decider active and intentional, making sure it connects to their Why. And ironically, because they expect the worst (in a manner of speaking), they are actually happier.

So what would your life look like if you simply assumed the worst, that there will never be more time, lighter work, or whatever. What do you want your life to be like in spite of all that?

If something surfaced for you, that’s a great start. The next part is figuring out what to do with what you now see, and that’s the part coaches like me help people with. If you are sitting with something you cannot quite name (a relationship, a pattern, a quiet sense that the current arrangement is costing more than it is paying back), I would be glad to have that conversation with you.

Because the season you are waiting for? It is not coming. But the relationships you are building, or quietly not building, are very much here. Especially that relationship with yourself.