Solopreneurs make dozens of business decisions every day. Which client to prioritize. Whether to raise rates. Which tool to try. In a corporate job, there are committees and approval chains to share the decision-making load. When you’re running a solo business, every call is yours.

When I was a product manager, I learned to sort decisions into two categories: ones you can easily reverse and ones you can’t. It sounds almost too simple, but it changed how quickly I moved and how much I deliberated. That same framework can be applied directly to running a solo business.

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\Most people use AI like a search engine: type a question, get an answer. It’s an easy, well-understood use case for tools like Claude, Gemini, and ChatGPT.

But for solopreneurs, the real value is in setting up dedicated projects with a lot of background information about your business. Most AI tools let you create project workspaces where you can add context about who you are and what you do. You can attach relevant files, and keep the conversation focused on one specific idea or area of your business.

I have 23 AI projects in Claude for everything from strategic planning to building a website. Some are used a few times per month, while others I rely on almost daily.

Here are a few of my favorites.

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When I worked a corporate job, I was often in charge of purchasing decisions. At one company, my team had inherited a lot of homegrown solutions. I saw the limitations of these products and was quick to replace them if the budget allowed.

In corporate settings, “build vs. buy” is a well-known decision framework. Companies weigh the cost of developing something in-house against purchasing an outside solution. It’s often simple math: how much time and resources does it take to maintain this internally versus what does it cost to buy or outsource?

Solopreneurs face the same decision constantly. However, the stakes are a lot higher when it’s your own time and own money as decision factors.

Knowing when to DIY and when to hire out is one of the most important operational decisions a solopreneur makes — and one that’s hard to figure out until you’ve been through it a few times.

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A lot of people go out on their own after a layoff, especially in the current economy. And when they do, they tend to focus on what they don’t know: how to find clients, how to set pricing, how to market themselves. But a long corporate career also builds some core competencies that translate directly into running a solo business.

I spent 15 years in a corporate environment, including a role on an executive team. I pivoted to a new career, and then found myself laid off 18 months later. I made the snap decision to start my solo business the next day.

While a lot of aspects of starting a solo business were intimidating, there were a few things I knew I could do well, based on my corporate experience. If you find yourself in a similar situation, here are a few corporate skills that might lend well to your solo career.

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At any given time, I’m juggling multiple clients. That means I’m juggling context for multiple projects, background information on various companies, and a lot of deadlines. Some of my clients give me a steady stream of work each month, while others pop in with a request every few weeks.

Whether you’re coaching, doing creative work, or have long-term retainers, most solopreneurs eventually find themselves managing multiple clients simultaneously. The number of clients you take on directly impacts your income, but more clients also means more complexity.

In my corporate life, I worked as a product manager at a software company. Even though my work is very different now, much of the project management follows the same basic concepts.

When running a solo business, you need to estimate your capacity, plan for future work, and not lose track of 100 moving parts.

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When I first started my freelance writing business, I assumed I should find clients who would put me on retainer. The appeal seemed obvious: steady income for me, predictable working relationship for the client. I even knew how to structure retainer agreements based on my prior roles at marketing agencies.

But a few months into a solo career, I was willing to take any work that came my way. Which was primarily project-based work, not retainers. I quickly built a business based on ad hoc assignments from many clients, rather than relying on a few.

The conventional wisdom would say that I was “doing it wrong.” Every solopreneur forum, coach, and freelancer community says the same thing: lock in recurring clients. But after three-plus years of running my solo business on almost entirely project-based work, I’ve found the opposite to be true. Chasing retainers isn’t the only path to a sustainable solo business… and it might not even be the best one.

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At one point in my life, I managed a team of seven. My days consisted of 1:1 calls, performance reviews, and running interference between the team, other departments, and customers.

I thought that’s what I wanted: the perceived power and responsibility of being a manager. But in reality, it was very stressful.

Today, I have been a solopreneur for three years. The assumption is that solo businesses are a starting point. You launch alone, build momentum, hire employees, and scale. That’s the entrepreneur’s playbook, right?

But over 80% of small businesses in the U.S. have no employees, according to the U.S. Small Business Administration. For many of us, that’s not a limitation. Staying solo is a deliberate strategy that prioritizes control and flexibility over growth for growth’s sake.

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I’ve worked remotely since 2006 (way before it was common). However, my days were filled with calls to colleagues and DMs to chat about everything from work to what we had planned for the weekend.

Now I’m a solopreneur. I have occasional calls with clients, but they’re rare. Most of my days are spent working alone. In many ways, this is great since I have the freedom to work however and whenever I want. But staying motivated when it’s just me requires me to be really thoughtful about how I work.

According to a 2025 report by Leapers, nearly half of self-employed professionals feel lonely occasionally or some of the time. One in five feels lonely or isolated often or always. It can be really hard to stay motivated when you’re working in isolation. You have to create your own structure and find ways to keep going without other people around.

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One of the things that I love about working for myself is that I don’t need to ask anyone’s permission before making a decision. If I want to make a change, I go for it, on whatever timeline makes sense for me.

But the freedom of solopreneurship can be a double-edged sword. Since you don’t need approval from other people, nothing is stopping you from chasing every shiny tool, course, or strategy that promises to solve your problems.

The ability to say no to distractions is an underrated skill for solopreneurs. There’s a difference between making strategic business decisions and letting yourself be pulled in a million directions. You need to master the former and resist the latter.

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It’s Friday afternoon, and a potential client just emailed asking about your services. You scramble to find your pricing (where did you save that document?) You dig through old emails for a proposal you sent six months ago that you could adapt. You piece something together and curse your past self for not being more organized.

This scenario plays out constantly for solopreneurs. Most chalk it up to the chaos of running a business alone. But constantly scrambling will start to cost you as your business grows — and eventually hold you back.

Most solopreneurs think that “operations” is something only real companies need: businesses with employees, office managers, and HR departments. But the absence of basic systems wastes your time, causes unnecessary stress, and makes you look amateurish to potential clients.

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I had to submit my resume for a role. Then I went through three interviews, with nearly identical questions each time.

The biggest problem? The role was for a freelance writing position. Not an employee of the company. I got all the way to the third interview only to learn that the role paid a fraction of my usual rate — even though I’d provided my rates upfront.

I’m experienced enough as a solopreneur to know that going through three interviews was a bad sign. The potential client wasn’t communicating internally (as confirmed by the fact that my rate had been overlooked). Repeated interviews are incredibly uncommon in my line of work, and indicated to me that the company didn’t know how to work with a freelancer.

When you’re a solopreneur, bad clients cost you time and money. They also crowd out better opportunities and put a strain on your bandwidth. Client selection is a core business skill. And if you’re not in a position to turn down work, you at least need to know how to handle sticky situations when they come up.

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Running a solo business can feel like operating without a map at times. Sometimes, you can stumble through the path, figuring things out as you go. Other days, you look around and realize that you’ve wandered pretty far off course.

One of the hardest parts is not having anyone to rely on for guidance. That’s why community matters so much for solopreneurs. Rather than operating in a vacuum, you can bounce ideas off other people. Or, you may find that community reduces your feelings of loneliness and isolation.

The sooner you find (or build!) a community, the easier it becomes to navigate the inevitable ups and downs of being a solopreneur.

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Most people think of solopreneurs as a one-person machine. The solopreneur (according to social media…) sends invoices, juggles client calls, manages marketing campaigns, and troubleshoots their own website — all before lunch. It’s a compelling narrative because it celebrates endless hustle and grit.

But it’s also a myth. Solopreneurship simply means you make the business decisions. You don’t have to consult anyone else or wait for approval. It doesn’t mean you’re the only person doing the work.

Most solopreneurs eventually bring in support (including me, in my solo business). Hiring help doesn’t mean you’re “no longer a real solopreneur.” It’s a sign that your business is growing. You recognize the value of your time or the limitations of your skillset.

Smart solopreneurs hire help as an investment. Outsourcing work or projects can expand your bandwidth while still allowing you to maintain full control over the direction of your business.

When to bring in professional support

One of the hardest parts of running a solo business is deciding when to get help. Many solopreneurs wait too long because they assume they should be able to do everything themselves. But if you feel like you’re working endless hours or you’re spending too much time on tasks, it’s probably time to hire.

Think of hiring as a strategic business decision, not a financial “splurge.”

Accounting or legal help

The first category many solopreneurs consider is financial and legal support. They recognize that they don’t have the expertise needed — and financial or legal mistakes can be costly.

An accountant or bookkeeper can manage tax compliance, keep your books clean, and help you understand your cash flow. Their jobs are to be familiar with accounting and tax laws, so you don’t have to stress. Typically, accountants or bookkeepers provide ongoing (monthly) support.

Legal help becomes important as your business grows in complexity. A lawyer might review your client contracts or help you navigate trademarks if you’re developing a brand. Depending on your legal structure, you may also need a lawyer to help with documentation like Articles of Organization (for an LLC). You don’t need a lawyer on retainer. Even a few hours of legal support per year can prevent legal problems later.

A virtual assistant

A virtual assistant (VA) is often the first hire for solopreneurs who are stretched thin. A VA can manage your inbox, follow up with clients, organize your files, or complete other organizational tasks that eat up hours of your time each week.

I rely on a lot of automation in my business. Tasks are completed automatically in the background between apps (using Zapier). But eventually, I reached a point where I couldn’t automate anymore. Some work needs a human touch. It was either me, or a virtual assistant. I chose to hire a VA so I could focus on the more strategic/creative parts of my business.

Most VAs work on an hourly, project-based, or monthly retainer model. With the right VA, you can start small and expand later if needed. Even a few hours per week can give you breathing room and help you stay focused on the work that generates revenue.

Project-based work

Not every type of help needs to be ongoing. You might hire a specialist when you’ve hit the limits of what you can do yourself.

For example, for a long time, I created my own brand assets. Eventually, I hit the limits of what I could do in Canva and wanted a more professional look for my business. I hired a brand designer to create my logo, choose fonts, and clarify my brand messaging. He gave me hundreds of Canva templates for various purposes.

If you need a website, a brand refresh, or automation support, a temporary engagement with an expert might make sense. That way, you don’t have to spend your time acquiring skills you don’t otherwise need and can start using the “finished product” quickly.

Building a team that supports your business

Before I started my own business, I was a manager in the corporate world. Being responsible for other people’s career success was hard for me, and I don’t think I was particularly good at it.

Bringing on help as a solopreneur doesn’t mean you have to become a “manager” in the traditional sense. Often, you’re hiring other independent professionals, like you. With the exception of a virtual assistant (who has to learn your systems/processes), the people you hire may not need a ton of oversight or hand-holding.

Bringing in help doesn’t have to mean building a team in the traditional sense. But before you hire, you should consider these three things:

• Revenue stability: Can your income support this additional expense?

• ROI: Will freeing up your time allow you to earn more or reduce stress in a meaningful way?

• Alignment: Does delegating this work directly support your business and create value?

If the answer to any of these questions is “no,” you may not be ready to hire yet.

Solopreneurship doesn’t mean doing everything alone

Your business works best when you’re working in your strengths. The rest can be delegated or outsourced.

I’m not a designer, so I hired someone to help me with design. I’m not an accountant, so I hired someone to help with my bookkeeping.

You’ve got to know which parts of your business you should hand off so your business can thrive. The goal isn’t to grow headcount, like a traditional business would grow. It’s about protecting your time and energy — the greatest assets your solo business has.

Thank you for your support of Work. Better. If you want me to answer a question about careers or career pivots that you’d like me to answer in a future issue, send an email to annabyang@substack.com.

Most solopreneurs don’t think about long-term leave until they’re already in crisis mode. A major illness. A family emergency. Or even a planned event like parental leave. And yet, every solo business — regardless of industry — faces the same vulnerability: when you step away, the entire business pauses with you.

When I first started my solo business three years ago, I wondered, “What would happen if I got really sick and couldn’t work for a few weeks?” If I don’t work, I don’t get paid, so I always knew this was a risk.

Never in my wildest dreams did I think “brain tumor,” but that’s what I was diagnosed with earlier this year. Suddenly, I was faced with the reality of stepping away from my business for months, not weeks. I had about six weeks to prepare between diagnosis and surgery.

The truth is, operational readiness matters far more than we assume. And the time to think about it is long before you need to.

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Leaving your corporate job for a solopreneur path is a bold move — and it can feel terrifying. But as long as you’re prepared, it can be a smart move, especially in the current rocky job market.

I worked at one corporate job for 15 years. Then I pivoted to a new career in marketing. Eighteen months later, I was working for myself as a full-time freelance writer. Within two months of going solo, I had replaced my salary at a marketing agency, but I’d also taken a lot of baby steps in advance of making the switch.

If you’re a solopreneur, you can make the transition easier if you build a safety net before you walk out of the corporate door.

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You’ve decided to start a solo business. Congratulations! I’ve been a solopreneur for years and love being my own boss.

My decision to become a full-time freelance writer happened overnight. I lost my full-time job at a marketing agency. Looking around, the job market seemed bleak. Working for myself was a way to start earning money immediately to pay bills.

However, I’d been thinking about a solo business for months. So while the timing wasn’t my decision, it was a direction I was headed anyway.

I had been freelancing alongside my 9-5 job for a few years, so I had the “infrastructure” in place to turn my side hustle into a full-time business. What you need on Day 1 is a lot different than what you need on Day 1,001.

Here are some of the minimum things you need to get started.

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I spent several years of my career in the uncomfortable role of middle manager. On one side, I had executives asking me why my team couldn’t “do more,” and on the other side, my employees told me they were stretched too thin.

It was an endless tug-of-war. I was both the enforcer of company expectations and the advocate for my team’s needs. At times, my role felt at complete odds with itself. Executives push for efficiency and growth, while employees look for empathy and stability.

Middle management, understandably, feels like a pressure cooker.

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When I first ventured into self-employment a few years ago, I received a lot of advice from fellow freelance writers: Know your worth. Don’t take low-paying work.

The advice was valid, as too much low-paying work is a recipe for burnout. But to the newly self-employed, I would say: Know your worth. And also, there are very valid reasons to take low-paying work, if it can help launch your business.

You can open the right doors without selling yourself short.

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When announcing her new album on the New Heights podcast, Taylor Swift said, “You should think of your energy as if it’s expensive… Not everyone can afford it.” She was encouraging people to have a healthy relationship with social media and not get sucked into online drama and endless scrolling.

As a working mom with three kids, this hit me deeply — about much more than social media. I have spent a good portion of my adult life talking about productivity, apps, and tools to save time. But Swift used a different word: energy. I can do dozens of things to save time in my day, but if I don’t have any energy left, what have I really gained?

If you want to treat your energy as if it’s expensive, you should think about how you’re spending your time and what things drain too much of your finite energy resources.

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You dream of quitting a toxic job, pivoting to a new career, or starting your own business. But there’s a financial reality to such a move: can you afford to earn less?

In 2021, I quit a job as an executive at a tech company. I pivoted into content marketing and journalism, and, initially, I was earning about one-third of my previous salary. But I had spent months looking at our household budget, and was prepared to earn even less.

When you’re determined to make a change, you’ll look at your finances differently. You should calculate your “freedom number” and understand the changes you need to make in your budget.

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