Your 2026 Doesn’t Need a Better Plan. It Needs a Better Vision.
Why business coach Holly Howard believes visioning (not planning) is the real foundation of founder clarity.
Ally here! In January, the air shimmers with the promise of a fresh start, the vast expanse of the new year laid out before us like an untouched field of newly fallen snow.
This often feels especially true for business owners and leaders. Everything can be different this year, if only we set the right plans. But where to start?
If your vision for 2026 includes revamping your career and business goals, there is no better guide than the inimitable Holly Howard. The founder of Pyramid and Ask Holly How, Holly is also Daly’s day one, ride-or-die business coach.
In this month’s issue, Holly explains the concept of “visioning” and why it’s a vital precursor to any tangible planning meetings you might already have on the calendar for Q1.
It’s a fitting time, because she’s on the precipice of her own fresh start, too. 2026 is shaping up to be a big year for Holly, in which she transforms from business consultant extraordinaire to launching Pyramid as a workplace tool that’s paving the way for a seismic shift in how we work.
Let’s hear from Holly — and founders: take note!
Ally: Let’s start broad: How do you define a “visioning session” and why do you think this is an important exercise for founders & leaders to undertake regularly?
Holly: A visioning session is when you take time to reflect on what it is you want to build (not what you think you’re supposed to build!), then outline how you will bring that to fruition, and consider the impact your vision will have on others.
Key words from that previous statement include: reflection, supposed, consideration, outline, fruition.
A vision without reflection is a reaction.
A vision built on what you think you’re supposed to build vs what you desire to build is an empty vessel.
A vision without consideration of impact is irresponsible.
And any of it without an outline of action and the roadmap to bring it to fruition is just daydreaming. Not that I don’t love to daydream! But that’s not the same as visioning.
To get more tangible: I always say a visioning session should be one part existential and one part concrete.
More ‘existential,” reflective questions include prompts like:
In the past year, what lessons did we learn? What milestones did we achieve?
As a founder / leader, what changes did I experience in my personal life that might have impacted the business?
What happened in the economy? In my community? And how might those things have an impact on my business?
What does growth mean to me?
How do I want to be spending my day within this company, and in life in general?
What impact do I want to have on my team, my community, the world? Both now, and 10 years from now?
Concrete questions include prompts like:
Where do I want my company to be located?
What customer base do I want to serve?
How much money do I need to put in my pocket to sustain my life now, and 10 years from now?
Am I going to have children, take care of an aging parent, take long sabbaticals, buy a house? All of these things inform the vision and trajectory of your company!
Do I want to manage a team — and if so, what size is the right size for my capacity and goals as a leader?
Once you’ve finished your reflection, you can start to paint a more tangible picture of how you will bring your vision to life. It’s important to make your vision specific, present, and time-bound. What are the concrete actions everyone will take, and what do you anticipate as the impact?
Ally: How does one structure a proper visioning session? Who from the company should be involved?
Holly: The word “proper” is interesting, because it makes it seem like there’s only one right way to do this. But as long as you tap into your own inner knowing, visioning will look different for everyone, based on how you create.
First, this can be done in a single session, but if it’s done right, it’s probably going to take multiple sessions, because it’s going to unlock so much clarity and self-awareness.
In terms of who should be involved: the vision is first and foremost the founder’s responsibility. You cannot outsource your vision to your team!
First, you must establish your “acorns” as a founder — the tiny seeds your team can build upon, such as top-line revenue and company-wide initiatives that will broadly impact each area of the business.
As a founder, you might need a few sessions to reflect and gather your own thoughts about where you desire the company to head.
Then, you can share that high-level vision with your team. and guide them to develop their own specific and strategic plans, goals, and KPIs for their departments that ladder up to this vision.
I call this building the “oak tree” from those foundational acorns.
Usually, teams need guidance on this, especially if they’ve never been trained on this type of work before.
I hope you can now see how visioning quickly becomes a multi-day/step process!
Ally: How do you differentiate visioning from a planning meeting? Both tactically and in terms of ~ vibes~.
Holly: Planning comes after visioning.
The vibes of visioning are, as I mentioned, much more existential and reflective. You should get messy when you are visioning. Creativity is a messy process; that makes a lot of entrepreneurs uncomfortable because we’ve been taught that business has to be buttoned up.
Once you get through the creative visioning process, planning can, in turn, become concrete, definitive, quantifiable, and timed. It might take a subset of the vision and map out in greater detail the specific goals and KPIs that we need to focus on to get there.
Ally: What’s the most common mistake you see founders make when it comes to setting their goals and intentions for the year ahead? Where do leaders get caught up, and how do you help guide them towards better mental framing or solutions?
Holly: Biggest founder mistake: falling prey to imitation, rather than building the business that is specifically right for their strengths, vision, and capabilities.
Too often, entrepreneurs look out to the market and their peers and try to imitate, and expect to find success there. It’s why so much capital flows to startups that don’t go anywhere. So many companies are just derivatives; everyone is hypnotized by FOMO.
In this saturated landscape, imitation is not a sustainable strategy! At Pyramid, we have a concept we call Workplace 2.0, which starts with defining your personal Point of View and how that influences the business you create in the world. It’s not about ideology. It’s about experience: what have you learned through your unique lived experience and how does that influence what you create and how you lead?
So the first thing I do is help people understand themselves on a much deeper level, and how that informs their values and desires for what they are building in the world.
Maybe you don’t want to build a team but feel pressure to because you think that’s what success is all about.
Or maybe you want to build something big, even when your peers think that’s selling out.
Both are valid, but go wrong when they aren’t aligned with your core values and vision as a founder.
After that, it’s about baby steps and accountability. We’ve been brainwashed into thinking change happens quickly and overnight. It doesn’t! It’s a marathon that requires constant regeneration and adaptation. Even the clearest visions won’t pan out if the actions aren’t broken into baby steps for everyone to take throughout the year. Staying accountable to those baby steps is actually harder than people realize, because we get intoxicated by fires and the emotions of change that we lose our commitments.
Not knowing one’s own needs and capacity is usually why entrepreneurs can’t sustain themselves, more so than any fluctuations in the market.
Ally: What’s been the most surprising thing (idea, decision, pivot, etc) that you’ve seen come out of a client’s visioning session?
Holly: I’ve seen it all! Lots of decisions to limit team sizes, cap revenue goals, and create truly sustainable companies that best fit a founder’s lifestyle and capacity.
I’ve even seen people decide to close their business after a deep visioning session. There’s no greater liberation than realizing that what you’ve been building is not actually how you want to be spending your day.
I love it when a founder finds the clarity to step away and make more time for their creative practice, by properly setting up their teams and building the right infrastructure to support everyone involved.
I think of someone like designer Rebecca Atwood: a few years ago, we worked together to create a plan that would allow her to split her time between 3 days/week in her painting studio, and 2 days/week focusing on her business. It doesn’t flow perfectly every week, but it did open up a new path forward for her painting, and it strengthened her leadership as she prioritized her own needs. By sustaining herself first, she now has more to give her team in terms of depth.
There is truly no ‘one way’ to be a successful entrepreneur. The question becomes: are you willing to indulge in the wisdom of uncertainty when you declare a vision that no one else has validated?
Ally: What’s on Holly Howard’s vision board for 2026?
Holly: I vision-boarded an F-150 three years ago, and just got it as my Christmas gift to myself. The vision here is to spend more time traveling across America, sleeping under the stars, and connecting with entrepreneurs all across the country.
It’s a big year for America: we turn 250, the midterm elections are coming up, Mamdani is at the helm in NYC, Dudamel arrives in the fall, the Knicks will make the NBA Finals ;) — and Pyramid will be woven into the fabric of entrepreneurship.
The whole dialogue we’ve been engaging in during this Q&A is why I built Pyramid. Most entrepreneurs weren’t taught how to build a business, they were taught how to get a job. So they follow generic advice from ChatGPT and other people’s playbooks.
Pyramid’s thesis is that the soft skills you were told to ignore in business school are actually the foundation that everything else your company needs to succeed rests on. We’ve been perfecting our methodology for 13 years with thousands of entrepreneurs. We’re building the beta now alongside a community of founders at Pyramid.work.
Pyramid is a strategic planning tool that helps entrepreneurs figure out their values and vision, then builds out all of the strategy and operations from there — from acorns to oak tree.
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The Cherry on Top: If this Q&A piqued your interest, you don’t have to wait for our beta to launch to learn more. Sign up for our newsletter at Pyramid.work. We’re doing free monthly seminars on topics just like this, and have great programming lined up for this year!
Holly Howard is the founder of both Ask Holly How, and Pyramid.work (coming soon!)