Inspired by Jason Lyman’s approach (Microsoft, Dropbox, Customer.io), adapted for the “I wear every hat in this business” crowd
Have you ever built a beautiful, color-coded, Pinterest-worthy annual marketing plan… only to abandon it by mid-February like a forgotten gym membership?
You are not alone.
Most annual plans fade early. A surprise in Q1 shows up, the market shifts, priorities change, or you simply realize that Past You was a little too optimistic about Future You’s energy and calendar.
Jason Lyman, CMO of Customer.io, takes a different approach. And it works whether you’ve got a big team or just you, your laptop, and an emotional support iced coffee.
Here are Jason’s five steps, translated into solopreneur-speak.
Your marketing strategy should be connected to the broader company strategy. In other words, you cannot pick tactics until you know what the whole business is actually trying to do next year.
Too many solopreneurs start with a list of actions: “I’m going to post on social every day!” “I’m launching a podcast!” “I’m buying ads and hoping for the best!”
But if those things don’t point directly toward your business goals, you have a plan held together by vibes instead of strategy.
Before you plan ANYTHING, ask yourself:
- What are my top 3 business goals this year?
- Where am I investing my time and money?
- What is keeping me (the CEO, COO, CMO, and intern) awake at night?
Your marketing plan should answer those things, not distract from them.
Step to start:
Before opening a Google Doc, spend 30 minutes answering this: what are three things you could achieve next year that would change the game for your business? Your marketing exists to serve those outcomes.
The Play to Win framework helps connect strategy to resourcing. Answer these five questions, in order, to give yourself structure, direction, and clear reasoning for every decision.
1. What is your winning aspiration?
This should be specific and measurable. Instead of “get more clients,” try “become the go-to designer for eco-friendly brands.”
2. Where will you play?
Who exactly are you selling to, and where do they hang out? “Everyone” is not a target audience. Get specific about industry, stage of business, and platforms.
3. How will you win?
These are your three to five big strategic content pillars. They serve as the core themes that keep your message focused, your content consistent, and your marketing aligned with what your audience actually cares about.
For example:
- Build authority through short-form video
- Launch a productized service
- Grow partnerships with complementary creators
4. What capabilities must be in place?
What do you need to do or have to make those pillars real? That might look like a consistent content calendar, a simple CRM, a virtual assistant, or even just protected deep work time.
5. What systems are required?
Think tools, budget, and workflow. The goal is not to overcomplicate things, but to be intentional.
The big payoff is that your marketing plan becomes a map, rather than a pile of tasks.
Step to start:
Choose one clear winning aspiration and draft your three to five content pillars that support it. Then identify one capability and one system you need to put in place to make those pillars achievable.
Healthy marketing plans balance high confidence work with experimental bets.
Solopreneurs tend to land on one of two extremes: (A) They repeat whatever worked last year and never try anything new, or (B) they make massive, terrifying bets that would require superhuman output to sustain.
Instead, split your energy like this:
- 70%: High Confidence (your money-makers).
These are the channels and offers that reliably work, such as your email list, referrals, a signature service, or a consistent content pillar. - 20%: Medium Confidence (smart tests).
These are structured experiments. Maybe they work; maybe they don’t. Think webinars or workshops, a small paid ad test, or finally trying short-form video in a consistent way. - 10%: Game Changers (moonshots).
These are your big, potentially transformative bets, like launching a SaaS, creating a high-level course, or building a brand new product line.
Do NOT pour everything into the 10%. That’s how business owners end up tired, broke, and stressed. The goal is to expand and evolve without putting the entire business at risk.
Step to start:
Audit your current and planned marketing activities, then categorize each one into 70, 20, or 10. If everything lands in the 70% bucket, add a few thoughtful experiments. If everything belongs in the 10% bucket, scale back until the basics are covered.
Keep your strategic pillars consistent but let the tactics flex. Entrepreneurs need this tattooed somewhere visible. Your plan isn’t supposed to be rigid. Rigid things eventually break.
Your strategic pillars (your three to five big bets from Step 2) stay consistent throughout the year. Everything else—your specific tactics, campaigns, and platform use—can move around.
Here’s a practical planning structure for solopreneurs:
- Annual: Define your strategic pillars.
- Quarterly: Review your progress, run experiments, and adjust non-pillar tactics.
- Monthly: Create your specific tactical plan (what gets posted when).
- Weekly: Focus on executing your workflow.
It also helps to separate your KPIs (Key Performance Indicators), which are nonnegotiable goals like revenue, lead volume, and subscribers, from your OKRs (Objectives and Key Results), which are stretch goals like launching a new offer or testing a new channel.
This separation allows you to adjust your tactics on the fly without losing sight of your core financial targets.
Step to start:
Create your annual, quarterly, monthly, and weekly planning structure in a single document or dashboard. Add recurring review dates to your calendar so adjustments become part of your system instead of something you only do when things feel off-track.
Anchor your plan around what you want to complete in the first month.
Many entrepreneurs ease into January slowly, and that gentle start often lingers much longer than intended. The result is a year that feels reactive instead of intentional.
Instead, pick one specific, measurable January goal. Not a quarterly goal, and not a huge annual project. Focus on something you can reasonably achieve in 30 days and that will make the rest of the year easier.
For example:
- Publish eight pieces of content
- Build your email nurture sequence
- Launch your lead magnet
- Clean up your CRM and workflows (or setup a CRM)
A strong, focused first month gives you momentum, clarity, and data you can use to refine the rest of your plan.
Step to start:
Set a 30-day January sprint. Make it doable, commit to it fully, and use that momentum to carry you into the rest of Q1.
Your marketing plan does not need to be perfect. It needs to be aligned with your business goals, grounded in a few strong pillars, and flexible enough to evolve as you do.
When you stop chasing random tactics, connect your strategy to real resources, and give yourself room for both safety and experimentation, you create a plan that feels manageable and meaningful instead of overwhelming.
At Videre Creative, we love helping service-based business owners and solopreneurs turn big ideas into sustainable, strategic marketing plans they can actually follow.
If you want support building a plan you will not ghost by February, let’s talk about what that could look like for your business.
