One of the best things about being a solopreneur is that nobody can tell you what to do. Candidly, the control freak in me loves that — at least partially.
Partially because, unfortunately, that’s also one of the worst things about being a solopreneur.
You can launch whatever you want, charge whatever you want, and change your entire business model because you had an epiphany in the shower.
You can decide to start a podcast even though you hate talking, launch a course nobody asked for, or spend three months building a funnel for an offer you’ve sold exactly twice.
And who’s going to stop you?
Your audience will cheer you on. Your friends will tell you it’s a great idea. Meanwhile, you’re making decisions that could cost you thousands of dollars and months of your life, often without anyone questioning the assumptions behind them.
I think this is one of the biggest vulnerabilities of running a solo business.
When you’re the only person making decisions, your blind spots can become company policy.
And the longer you operate without anyone challenging them, the more expensive those blind spots can become.
The danger of always being the smartest (or the only) person in the room
I talk to solopreneurs all the time, and many of them are exceptionally good at what they do.
They’re experienced consultants, coaches, marketers, and other experts who have spent years developing skills that people are willing to pay good money for.
They understand their industries. They know their clients. They’ve built businesses from scratch, often without much help.
That experience is valuable. It can also make it surprisingly easy to become convinced that you already understand the problem you’re facing.
And when you’re the CEO, head of marketing, sales director, and entire strategy department, it’s easy for an assumption to make its way through every stage of the decision-making process without being challenged.
You proposed it. You evaluated it. You approved it.
Congratulations on the unanimous board decision!
Speaking of decision fatigue, mine usually shows up when I need to update my website. I’m in the process of doing that (again!), so my friend Carolyn’s challenge couldn’t have come at a better time.
I need someone to tell me what to do before doing the actual thing (does that make sense?). Will I see you in the challenge below?
📣 Brought to you by 📣
The Get Your Site Together Challenge
‘Update my website’ has been on your list since January. You sit down, get going – then stall. There’s always stuff you didn’t know you’d need. Start. Stop. Repeat. 😵💫
Time to get your s*ite together! Nov 16-20th, Website Redesign Expert Carolyn Leasure will help you gather the 5 essentials you need BEFORE templates, designers, or copywriting – so you have a site that finally does what it’s supposed to.
Join the Get Your Site Together Challenge!
Want your name up here? Reserve your slot!
Disagreement is surprisingly good for your brain
Psychologist Charlan Nemeth at UC Berkeley has spent decades studying dissent and its influence on decision-making. Her research suggests that exposure to minority opinions encourages people to consider more information, examine alternatives, and think more broadly about a problem.
In one 1996 study with John Rogers, minority dissent encouraged participants to search for information on different sides of an issue, particularly when the issue was personally relevant.
This is important because we tend to look for information that confirms what we already believe (confirmation bias anyone?).
If you’ve decided that launching a new offer is the answer to your revenue problems, you’ll probably find plenty of reasons to support that decision. The internet has an almost supernatural ability to supply evidence for whichever conclusion you’d prefer to reach.
Someone who challenges your assumption forces you to examine possibilities you may have dismissed too quickly.
Of course, disagreement doesn’t automatically lead to better decisions. The person disagreeing might be spectacularly wrong.
The value comes from being forced to examine your reasoning, consider alternatives, and gather evidence you might otherwise ignore.
You don’t need someone to make your decisions for you. You need people who can help you make those decisions with fewer blind spots.
There are opinions, and then there’s useful disagreement
I think this distinction is particularly important today because the internet has given us access to an almost unlimited supply of opinions — and don’t even get me started on AI “advice”.
You can post a business dilemma on LinkedIn or Threads and have complete strangers explaining what you should do within minutes.
Some of that advice might be brilliant. Some might be terrible. A surprising amount will be people recommending whatever they happen to sell.
Everyone has a framework. Everyone has a method. Everyone has a very compelling reason why your biggest problem can be solved with their favorite marketing channel.
The challenge is figuring out whose advice deserves your attention.
Here’s how I think about useful disagreement.
1. The person understands enough of your business to challenge the right thing
Let’s say you tell someone you’re planning to raise your prices.
They might enthusiastically encourage you because they believe experts should charge premium rates. Or they might warn you that your audience won’t pay more.
Both opinions could be completely useless without context.
I’d want to know what you’re currently charging, what competitors charge, how much demand you have, what your conversion rates look like, what outcomes clients get, and whether your delivery capacity is already stretched.
(Yeah, I’m nosy like that.)
The person challenging you should understand enough of the situation to identify the relevant trade-offs.
And when they lack information, they should be willing to ask questions before dispensing wisdom.
2. They’re willing to tell you something you don’t particularly want to hear
We all like encouragement. There’s nothing wrong with that, especially when you’re running a business and dealing with rejection, uncertainty, and the occasional spectacular failure.
But encouragement becomes considerably less useful when it’s the only response you ever receive.
Sometimes you need someone to tell you that your offer is confusing, your revenue projections are wildly optimistic, or you’re spreading yourself too thin.
“I need someone to tell me that my baby’s ugly” is something I recently heard from a Council member who was looking for exactly that — a place where their ideas are pressure-tested rather than blindly agreed with.
Which brings me to the next point.
3. They can disagree without being an asshole
There’s a particular breed of business expert who believes being brutally honest means having a permanent license to be unpleasant. They take pride in telling people uncomfortable truths, preferably in the most theatrical way possible.
I have limited patience for this.
The purpose of challenging someone’s thinking is to improve the decision, and that requires enough trust for people to share what’s actually happening in their businesses.
Psychologically safe environments allow people to speak candidly, disagree, and discuss mistakes without fear of humiliation.
However, psychological safety doesn’t mean avoiding uncomfortable conversations.
I think that’s an important distinction: you should be able to tell someone their strategy has serious flaws without making them feel stupid for considering it and without making it sound like a personal attack.
The interesting thing about being challenged is that you don’t have to agree
Personal example time: in the first months of running The Council, almost all founding members told me I should up the price. They thought I was charging too little for the access, support, and resources they were getting.
Now, it’s obviously lovely to hear people tell you that your work is worth more money. It’s even nicer when they’re the people paying for it.
But I didn’t immediately increase the price.
I wanted to examine whether the business fundamentals supported the recommendation.
Was demand strong enough? Were people actually getting the results I wanted them to get? Was the community becoming more valuable as it grew? Would the higher price make sense given the alternatives available to potential members?
Eventually, I did increase the price.
The interesting part is that those conversations prompted me to examine a decision I’d been postponing.
My members had a perspective I couldn’t fully replicate on my own: they were experiencing the value of The Council as customers.
I had the financial data and a much broader view of the business.
And that’s what good feedback should accomplish. It gives you information and perspectives that improve your judgment, whether or not you ultimately follow the recommendation.
Who gets a seat at your decision-making table?
I’ve been thinking about this a lot because, as solopreneurs, we often talk about building networks primarily in terms of business development: we want more referrals, introductions, collaborations, and opportunities.
Those are all excellent reasons to cultivate relationships.
However, I’d argue that having people who can help you think through difficult decisions is at least as valuable.
Ideally, you want access to three kinds of perspectives.
- People who’ve already dealt with a similar problem. They’ve made the mistakes, learned from them, and can help you avoid repeating the expensive ones. Their experience won’t always translate perfectly to your circumstances, but it can help you recognize risks you haven’t encountered yet.
- People who see your business from a different angle. A pricing expert might notice something a content strategist overlooks. A consultant working in another industry might recognize an opportunity that seems completely normal to your competitors and clients. Different experience creates different perspectives, and sometimes that’s exactly what you need.
- People who know you and your business well enough to spot your patterns. They remember that you’ve considered launching a course three times and abandoned it twice. They know which activities generate revenue and which ones you pursue because you enjoy them. They can tell when you’re repeating an old mistake with a slightly different haircut.
You don’t necessarily need dozens of people.
A few thoughtful, experienced people who understand your business and are willing to challenge you can make an enormous difference.
But there’s another side to this equation.
You have to give them enough information and permission to disagree.
If you only share your finished ideas and announce decisions you’ve already made, people will naturally respond with congratulations.
If you want useful feedback, you have to be willing to show unfinished work, disclose the constraints you’re dealing with, and admit when you genuinely don’t know what to do.
That can be uncomfortable, especially when you’ve spent years positioning yourself as the expert who has the answers (ask me how I know).
Well, since you asked: It took me ages to ask for advice when I was struggling. I was so damn married to the idea that a strategist has all the solutions that I felt like a fraud even when asking a simple question like “does this landing page look ok?”
I got over it when I started joining private communities and saw people who were incredibly accomplished ask others to tear apart their idea or their product. Then I saw them implement the feedback they got and win…again.
A little exercise: Find your next bad decision before you make it
Think about one important decision you’re currently considering. It could be launching an offer, changing your pricing, choosing a marketing channel, dropping a service, or entering a new market.
Now find someone whose judgment you respect and who understands enough of your business to offer an informed opinion.
Explain what you’re considering, why you think it’s the right move, and what evidence you’re using to support that conclusion.
Then ask them these three questions:
- Which assumption am I making that you would challenge?
- What am I overlooking that could make this decision backfire?
- What would you do differently if this were your business, and why?
Here’s the difficult part: listen to their answers before jumping in to defend your plan.
You might discover a flaw worth addressing. You might get a completely different approach to consider. Or you might emerge even more confident in your original decision because you’ve examined its weaknesses. All three are useful outcomes.
And if you can’t think of anyone you’d feel comfortable having this conversation with, I’d consider that a gap worth fixing.
Your independence shouldn’t become your biggest business liability
Last week, I wrote about the post-social internet and why I believe private networks and trusted relationships are becoming increasingly valuable. This week, I want to leave you with another reason to invest in those relationships.
Running a solo business means taking responsibility for every important decision. That’s part of the deal, and for many of us, it’s also part of the appeal.
But there’s a considerable difference between being responsible for a decision and having to figure everything out entirely on your own.
The most useful people in your business network will occasionally tell you something you don’t want to hear. They’ll challenge your assumptions, question your priorities, offer perspectives you hadn’t considered, and sometimes convince you to abandon an idea you were very excited about.
And they’ll expect you to do the same for them.
So, who’s challenging your thinking?
One of the reasons I built The Council was that I kept meeting experienced solopreneurs who had plenty of knowledge and very few people they could discuss their real business problems with.
Inside The Council, we work through decisions about offers, pricing, positioning, acquisition, and all the other things that keep independent business owners awake at night.
We have twice-monthly Decision Clinics, ongoing conversations and feedback in our private forum, and members with different backgrounds who bring perspectives I couldn’t possibly provide on my own.
I’m in there every day, asking questions, challenging assumptions, sharing my experience, and occasionally having my own thinking challenged.
If you already have a working business and want a group of experienced peers who will take your decisions seriously, I’d love to have you join us.
