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At work, we still talk about careers like they’re ladders. As if success must be a straight line upward: more responsibility, bigger title, better office.
But that old image isn’t just outdated. It can be harmful. Ladders come with an unspoken message: if you’re not climbing, you must be falling. If you experience job loss, the ladder metaphor makes you feel like you slipped off and can’t recover. If you take a step sideways, it makes you look like you stalled and aren’t motivated. If you change careers completely, it can feel like you have to start from scratch.
Most people don’t need any more pressure or extra worry about what others think, when they’re already trying to make hard decisions about their work and their lives.
That’s why I think we need a better metaphor.
Why a quilt is a better model than a ladder
Imagine a quilt. It’s not one long piece of cloth that stretches up into the sky. Instead, it’s many pieces, each with its own shape, material, color, and history, stitched together into something useful and uniquely meaningful.
That’s what modern careers look like:
- Pieces of skill you build over time
- Patterns of work that overlap and influence one another
- Mistakes, leaps, and detours that add texture
- Priorities and goals that can shift as life changes (sometimes by your own choice, and sometimes because a square ended before you expected)
A career quilt has direction, purpose, and depth. And unlike a ladder, it doesn’t require you to constantly compare your height to someone else’s.
How to think about your own career
If you’ve been picturing your career as a ladder, it’s easy to fall into critical self-talk about where you “should” be. You might feel behind or worry that a change means you’ve lost everything you’ve worked for. The ladder metaphor leaves very little room for life’s unexpected turns, or for choices that don’t look like a straight climb upward.
A quilt gives you a different way to look at your past, and your future. A job loss isn’t slipping off the ladder, it’s simply a square that ended before you expected. A pivot isn’t failure, it’s a new piece of fabric. A sideways move isn’t stalling, it’s part of your quilt that builds depth, resilience, and new skills.
So instead of asking, “What’s my next rung?” try asking, “What do I want my next square to be?” What skills do you want to strengthen? What kind of work feels most important to you right now? What chapter are you ready for, even if it doesn’t look like a promotion on paper?
Careers don’t have to be explained in a straight line to be valid. You’re allowed to choose your next piece intentionally, without worrying about how it looks from the outside.
How to support your team members’ career quilts
You don’t just stitch your own quilt. Managers (from first-line leaders through senior executives) have an enormous influence on whether your team members feel boxed into ladders or supported in building something broader. One of the most helpful things you can do is expand the conversation beyond titles and promotions, and focus instead on skills, experiences, and growth that can happen in many forms.
If someone feels stuck waiting for a promotion, instead of saying, “You just have to wait for the next role,” a manager might say: “Let’s look at the skills you want to build and how you can grow and demonstrate them in this role so you’ll be ready when the time comes.” That feels empowering and grounded, instead of simply waiting to be chosen.
If someone shares that they’re interested in trying something new, even if they’re not 100% sure it’s for them, respond with openness: “I’m glad you let me know. Let’s think about ways you can start getting exposure – maybe by shadowing someone, sitting in on a project, or meeting a few people on that team.” This acknowledges that growth often starts with exploration, not certainty.
And if someone shifts direction entirely – for example, moving from people leadership back into an individual contributor role – your words matter. Reminding them that it isn’t a step down, but another meaningful square in their career quilt can help make that transition successful, and it may matter more to them than you realize.
Redefining success
Ladders measure success by how high you climb. Quilts measure success by what you build along the way.
When we help people (including ourselves) see their careers in a different light, we stop equating promotions with progress. We start valuing depth over direction, learning over hierarchy, and stories over status. And careers become something people shape, rather than something they endure while waiting for their turn.
Because real growth isn’t about how high you go—it’s about shaping a career that reflects who you are and allows you to contribute something uniquely valuable along the way.
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Ever feel like your solo business is running you into the ground? Solopreneurs don’t have the luxury of handing off tasks to a team. Everything lands on your plate, and there’s never enough time.
AI won’t run your business for you (despite what some of the big AI companies would have you believe). But it can give you back hours every week. Some tools are AI-first, meaning their primary job is to perform an AI-driven task. You can also look at adding AI features inside tools you’re already using.
I rely heavily on AI in my solo business. I can get more done in less time, without sacrificing quality in any of my work.
Here are a few AI tools that can make a huge difference in a solo business.
Meeting notetakers
An AI notetaker was the first AI-first tool I added to my business. My notetaker auto-joins my calls, records the conversations, transcribes everything, and sends me a recap with action items. Instead of scrambling to remember what a client said three months ago, I have a searchable archive of every meeting.
This solves a real problem: You can be fully present during the conversation rather than taking notes by hand. You also don’t risk missing something important, which can happen with manual note-taking.
Tools: Otter, Fireflies, Fathom
Knowledge systems
Over time, solopreneurs accumulate a mountain of valuable material: proposals, client emails, blog drafts, research notes, and random thoughts. Most of it gets buried in folders (or notebooks), which makes it hard to track through your thinking or find related ideas.
A personal knowledge system changes that. It creates a searchable “second brain”—like your own Wikipedia. Add AI into the mix, and you can “chat” with your own content instead of digging through your notes and files. Think of AI as a personal research assistant who has read everything you’ve ever written.
Tools: Google NotebookLM, Tana, Notion AI, Reflect
Standard operating procedures
Even if you work alone now, you might eventually bring on help (like a virtual assistant, a subcontractor, or a specialist for a specific project). When that happens, you’ll need documented processes. The problem is that writing step-by-step instructions for everything you do is tedious. Most solopreneurs never get around to it.
AI tools solve this by recording your screen as you complete a task and automatically generating written documentation. You walk through a process once, and the tool creates a standard operating procedure (SOP), complete with screenshots and written instructions—without any extra effort on your part.
SOP tools are uncannily good. I usually only need to make small tweaks to the written version, and sometimes don’t need to make any edits at all. I store them on my Google Drive so I can easily share them if needed.
A business coach
One of the hardest parts of working solo is not having colleagues to bounce ideas off of. You make decisions about pricing, clients, marketing, etc., without a gut check from anyone else.
AI chatbots can serve as an on-demand sounding board. They won’t replace your judgment, since they can’t understand the nuance of the real world and human relationships. But they’re useful for thinking through options, drafting difficult emails, or walking you through the different angles of an idea you might have.
In Claude, I’ve created a “Business Coach” project. I’ve uploaded a lot of files so Claude has context, including information about who I am, the work I do, my brand, and the potential clients I’m targeting. When I’m trying to think through something, Claude asks me questions. By responding, I clarify my own thinking.
The key is prompting well. The more context you give about your business, your situation, and any constraints (like your time or finances), the more useful the output.
Tools: ChatGPT, Claude, Gemini
AI features embedded in existing tools
Every company has been rushing to add AI features to its products. Some are good. Some are included with your existing subscription, while others treat AI as an add-on.
For example, I rely on Airtable to run the “back-end” portion of my business. AI-powered “field agents” have been able to accomplish a lot of tasks I used to do manually.
A few other ideas:
- AI-powered transaction matching in accounting software like QuickBooks or Kick can categorize your expenses and spot anomalies.
- AI scheduling assistants in tools like Motion or Reclaim can help you plan your day and protect your calendar from too many meetings.
- AI email features in apps like Superhuman or Spark can draft replies or prioritize your inbox.
The tools you already pay for are getting better. If AI has been added since you originally signed up, the features are worth exploring.
Start with one new tool
AI fluency is becoming a baseline skill, like knowing how to use a spreadsheet. And it’s becoming ubiquitous: Apps will keep adding AI features to make work easier and faster.
But you don’t need to master everything at once. Pick the tool that solves an obvious problem or can complete a task that drains a lot of time from your day. Figure out how to get the most out of it before adding the next thing.
