🚀 TL;DR
- Entrepreneurs often confuse what clients think they should sell with what clients actually want—leading to missed revenue opportunities.
- There’s a key difference between upselling (going deeper on the same service) and cross-selling (offering a different service) for solo business owners.
- Upselling typically builds stronger client relationships, predictable income, and leverages what you already do well; cross-selling can diversify revenue but risks diluting your positioning and increasing complexity.
- Use client signals—the repeated questions, frustrations, requests during or after engagements—to guide whether a next step is an upsell or a cross-sell.
- Create a simple offer path: focus on deepening one transformation (via upsells), keep cross-sells light and highly connected to your core service, and build from true client demand rather than your own service catalog expansion.
For years, I’ve watched entrepreneurs have revenue opportunities slip away because they can’t tell the difference between what clients want and what they think they should sell them.
For example, a customer might finish a strategy engagement, and you pitch something adjacent—maybe implementation support in a different area. Sometimes it worked. Often, it felt forced. They'd seem interested, then they ghost.
The shift? Start paying attention to what clients asked for without you prompting them. The questions they raise repeatedly. The frustrations that keep surfacing even after you delivered the initial work.
Those signals teach you something: there's a massive difference between deepening value in the same lane versus broadening into new territory.
In this article, I'll explain how upselling and cross-selling work for one-person businesses and what the differences are.
What is cross-selling?
Cross-selling is when you sell an adjacent service or product to your client.
For example, a copywriter could offer social media graphics, or a web designer who adds brand strategy consulting.
The logic seems sound: you already have the client relationship, so why not expand what you offer them? You can increase how much each client spends per project. You diversify your revenue streams. You position yourself as a more complete solution.
But there's a cost most service providers don't see coming.
Benefits of cross-selling
Cross-selling can increase client spend per project without requiring you to find new clients. If you've already built trust through your primary service, introducing complementary products or services can feel natural—when done right.
It also diversifies your offers. Instead of being dependent on one revenue stream, you create multiple ways for clients to work with you. This can provide some buffer against market shifts or seasonal fluctuations in your core service.
For some businesses, cross-selling makes perfect sense. Amazon suggests related products. A gym offering nutrition coaching alongside training. These work because they're tightly connected to the customer's original goal, or as I call it, "The Big Win."
Risks of cross-selling
Cross-selling splits your focus across multiple services instead of deepening one.
Every additional offering you add requires its own marketing, delivery system, and expertise. You're now maintaining competence in several areas rather than mastery in one. Your positioning gets muddy because you're trying to communicate multiple value propositions at once.
I've watched talented consultants accidentally turn themselves into generalists by adding too many cross-sells. They started as specialists in one domain, then gradually became "the person who does a bunch of stuff." That makes you forgettable if you don't connect the services to the original goal.
What is upselling?
Upselling offers a higher-value or extended version of the same service the client bought.
For example, a website designer who upsells ongoing site maintenance or a marketing strategist who expands from campaign planning into full execution and management.
You're not introducing something new. You're going deeper with what's already working.
Benefits of upselling
Upselling increases lifetime value because you're stacking engagements with the same client around the same transformation. Instead of constantly hunting for new business, you're expanding existing relationships.
It deepens trust. The client has already experienced your approach and seen results. They're not evaluating you from scratch—they're deciding whether to go further with something already proven.
It builds predictable income. When you have a clear upsell path, you can forecast how many entry-level clients will convert to your core offer, and how many will expand into premium or retainer relationships.
The highest leverage revenue comes from building a clear path to upsells.
Risks of upselling
Upsells aren't automatically better just because they go deeper.
If they're misaligned with client goals, upsells can feel like unnecessary scope creep. You're trying to extend the engagement beyond what the client actually needs because you want the revenue.
The difference between a good upsell and a pushy one comes down to client readiness. A good upsell happens when the client has achieved initial results and naturally wants to expand. A bad upsell happens when you're manufacturing reasons to keep billing.
You can feel it in the conversation. When a client asks, "What's next?" or "How do we take this further?"—that's an organic signal.
When you're pitching expansion that nobody asked for—that's you projecting your goals onto their situation.
The differences between cross-selling and upselling
Goals
Upselling means going deeper into one problem. You're helping the client achieve more scale, more speed, or more comprehensive results around the same core transformation.
Cross-selling means spreading into other areas. You're introducing new problems to solve, new outcomes to achieve, and new expertise to demonstrate.
Upsells deepen the relationship by stacking outcomes. Cross-sells distract by stacking products.
Client psychology
An upsell feels like a natural next step from the client's perspective. They've already said yes to the problem you solve. They've already experienced your methodology. They've already built trust in your approach.
An upsell doesn't require a new decision—it extends an existing one.
A cross-sell feels like a new purchase. Even if it's related to your original service, it introduces new evaluation criteria. Does this person have the right expertise in this other area? Is this the best use of the budget? Should we compare other providers?
The client has to re-establish confidence in you, but in a different domain.
Revenue impact
Upsells build stability. They create retainers, longer projects, and predictable expansion paths. You can forecast revenue based on conversion rates between tiers.
Cross-sells create short-term spikes. A client buys one thing, then buys a different thing later. But each purchase is a separate sales cycle. There's no compounding momentum.
For solopreneurs, stability beats spikes every time. You don't have the capacity to chase new sales cycles with existing clients constantly.
When to use cross-selling or upselling
The strategic choice between cross-selling and upselling comes down to one question: Will this expand the client relationship in a way that serves both of us?
When cross-selling makes sense
Cross-selling works when the additional service is directly adjacent to your main skill and requires minimal new infrastructure.
A podcast editor offering show notes. Both services use similar skills, serve the same client goal (better podcast performance), and don't require completely different delivery systems.
A website designer offering hosting management. It's a natural extension of the build, uses overlapping technical knowledge, and solves an obvious client need.
The key filter: does this cross-sell genuinely serve the client's core outcome, or does it serve my desire for more revenue?
If you're considering a cross-sell, ask whether it builds leverage or spreads you thinner. You're probably better off staying focused if it requires entirely new skills, different client expectations, or separate delivery infrastructure.
When upselling makes sense
Most solopreneurs should prioritize upsells: retainers, done-for-you add-ons, and premium tiers.
Upsells make sense when:
The client has achieved initial results and wants to go further.
You have a clear path to deliver more value around the same transformation. The expansion serves their goals, not just your revenue targets. You can provide the upsell without spreading yourself across too many different systems.
After a strategy session, the natural upsell is implementation. After a project, it's ongoing optimization. After the initial results, it scales those results.
The best upsells feel inevitable rather than pitched.
Five tips to cross-sell or upsell as a solopreneur
Whether you're upselling or cross-selling, execution matters as much as strategy.
1. Build one clear Offer Portfolio
Don't offer ten things. Start with a simple progression: entry point, core service, premium tier.
Most solopreneurs overcomplicate their offerings because they're afraid of saying no. They end up with a service menu that confuses prospects and fragments their focus.
Pick one core transformation. Map the natural progression from entry to mastery. Build 2-4 clear tiers that serve that journey. That's it.
2. Design upsells as the "obvious next step"
After a strategy session, implementation is the obvious next step. After a website is built, ongoing maintenance is obvious. After initial results, scaling those results is obvious.
The best upsells don't feel like sales pitches—they feel like the natural continuation of work already delivering value.
This means positioning your entry offer with the larger journey in mind. When you sell a diagnostic engagement, you should be explicit that it's often the first step toward full implementation. Clients know from the beginning there's a path forward if they want it.
3. Keep cross-sells small and lightweight
If you cross-sell, ensure the add-on doesn't require significant new expertise, tools, or delivery systems.
Small services like templates, audits, or done-for-you components related to your core work can add revenue without adding complexity.
Major new service lines almost always distract more than they're worth. They pull focus, fragment positioning, and rarely generate the ROI you expect.
4. De-risk your upsells
Offer trial months, small pilots, or clear guarantees that make expansion feel safe.
The barrier to an upsell is usually the uncertainty of commitment. Clients worry about getting locked into something that doesn't deliver the expected value.
When you move clients from project work to retainers, offer month-to-month terms for the first three months. So, there's no long-term contract required. That flexibility made the decision easier while giving us time to validate the fit.
5. Use conversations as cues
Pay attention to what clients ask for during and after engagements.
When they say, "Can you also handle X?" that's either an upsell or cross-sell opportunity—but don't jump immediately.
Ask why they need that. What outcome are they trying to achieve? Would expanding your current work serve that outcome better than adding something new?
Sometimes what sounds like a cross-sell request is actually an upsell in disguise. The client wants more of the same transformation, they're just articulating it as a different service.
Upselling and cross-selling done right
For one-person businesses, upsells are the stability engine. Cross-sells are seasoning—useful in small amounts but it'll overwhelm everything if you use too much.
The solopreneurs who build sustainable businesses do it by going exceptionally deep in one transformation.
They create clear Offer Portfolios that make expansion feel natural. They listen to clients' signals about what's actually needed rather than push what they want to sell.
The revenue you're chasing through diversification usually sits in front of you, waiting for you to help existing clients go further with what already works.
