Self-Coaching When You’re Your Own Boss: Who Challenges Your Thinking?

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Episode: Self-Coaching When You’re Your Own Boss: Who Challenges Your Thinking?

What happens when every decision you make for your business is perfectly sensible — but those decisions keep you exactly where you are?

Fionn has been his own boss for eight years when a long-standing client offers him a substantial six-month project. Good fee. Good client. Familiar work. Saying yes seems obvious. But for almost two years, Fionn has been saying he wants to take his business in a different direction.

This WorkLife Story explores self-coaching for freelancers, founders, consultants and independent workers — and why sometimes the thinking that most needs challenging is the thinking that seems completely reasonable.

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Carmel O’ Reilly

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Fionn had been his own boss for eight years. Then a long-standing client offered him a substantial six-month project. Good fee. Good client. Familiar work. Saying yes seemed obvious. There was just one problem. For almost two years, Fionn had been saying he wanted to take his business in a different direction. And every sensible decision he made seemed to keep him exactly where he was. Welcome to WorkLife Stories from School of WorkLife. I'm Carmel O' Reilly. Today's episode is Self-Coaching When You’re Your Own Boss: Who Challenges Your Thinking? Today’s story is about Fionn. It's a story about the freedom of making your own decisions — and what happens when there's nobody else whose job it is to challenge them. An independent consultant, Fionn had built a good business doing work he was very good at. His clients trusted him. Several had worked with him for years. Most of his business came through recommendations and repeat work. He had the kind of professional independence he had once wanted very badly. Nobody told him what projects to take. Nobody decided how he spent his time. Nobody set his priorities. Nobody told him what direction his working life should take. Fionn made those decisions himself. And for a long time, that had felt like freedom. Then an email arrived from one of his longest-standing clients. An Easy Decision The client wanted Fionn to lead a substantial six-month project. It was familiar territory. Fionn knew the organisation. He knew the people. He understood the work and was confident he could do it well. The fee was good. Very good. As an independent worker, there was something deeply reassuring about seeing six months of income sitting in front of him. He didn't need long to think about it. He began composing his reply. I'd be delighted to. Then he stopped. The cursor blinked after the full stop. Something about the sentence bothered him. Not the client. Not the project. Not even the six months. It was the word delighted. Would he? Fionn deleted the sentence and closed the email. He would reply tomorrow. The Business Fionn Kept Meaning to Build For almost two years, Fionn had been talking about changing the direction of his business. He wanted to move away from the kind of delivery work that had occupied most of his time and towards more strategic work. He had ideas. Good ones, he thought. There was a new service he wanted to develop. Different organisations he wanted to approach. He had even begun writing about some of the thinking behind his work. Whenever he found time for it, he came alive. The problem was that he rarely found time for it. There was always client work. And client work paid. The new ideas didn't. Not yet. So the sensible thing was to keep doing the work that brought in the money while developing the new direction alongside it. At least, that was what Fionn had been telling himself for almost two years. The trouble was that alongside it kept becoming later. And later kept becoming another year. When Every Decision Makes Sense The following morning, Fionn opened a notebook. At the top of the page he wrote: Should I take the project? He divided the page in two. There were plenty of reasons to say yes. Six months of guaranteed income. A good client. Interesting enough work. People he liked. Work he knew he could deliver well. And there were the realities of working independently. Nobody guaranteed Fionn a salary at the end of every month. There was no employer paying him when business was quiet. Turning down good work in the hope that different work might eventually replace it wasn't necessarily courageous. It could simply be foolish. By the time he reached the bottom of the page, the answer seemed obvious. Take the project. Fionn looked at what he had written. Everything on the page was true. And yet something still didn't feel right. That was when he realised he had been asking himself the same kind of question for two years. Does it make sense to take this work? And almost every time, the answer had been yes. Who Challenges the Boss? When Fionn had worked inside organisations, his thinking had been challenged constantly. Managers questioned proposals. Colleagues disagreed with him. Meetings forced him to explain why he thought something should be done. Sometimes the challenges were useful. Sometimes they were irritating. Occasionally they changed his mind. He hadn't particularly appreciated that part of organisational life at the time. Now there was nobody sitting opposite him. Clients challenged his thinking about their businesses. They didn't challenge his thinking about his own. Friends would listen, but they weren't living with the consequences of the decisions. And when Fionn talked about the six-month project, most people reached the same conclusion he had. It sounded like a great opportunity. It was. That was precisely what made the decision difficult. Fionn didn't need somebody to tell him whether the project was good. He needed somebody to challenge the thinking that made taking it seem inevitable. There was nobody whose job it was to do that. Unless Fionn learned to do it himself. A Different Self-Coaching Question He returned to the notebook. Should I take the project? The question was reasonable. But perhaps it wasn't the question he needed. He crossed it out. For a while he didn't write anything. Then another question occurred to him. What am I saying yes to by saying yes to this? Fionn began writing. Six months of income. Six months of familiar work. Six months working with people he liked. Six months of financial certainty. Then he kept going. Six months in which the new service probably wouldn't be developed. Six months in which he wouldn't approach the organisations he had identified. Six months in which the writing would happen whenever he could squeeze it in. Six months in which the business he wanted to create would remain the business he intended to create. The project hadn't changed. The question had. And because the question had changed, Fionn could see something his first analysis hadn't shown him. He wasn't simply deciding whether to accept a good project. He was deciding what another six months of his working life would be used to build. When Good Decisions Keep You Stuck There was nothing wrong with the decisions Fionn had been making. That was perhaps the hardest thing to recognise. He hadn't been reckless. He hadn't made obvious mistakes. He hadn't repeatedly chosen bad clients or poor opportunities. Quite the opposite. He had made sensible decision after sensible decision. Take the work. Serve the client well. Protect the income. Keep the business secure. Individually, each decision was easy to defend. Collectively, they had created a working life Fionn kept saying he wanted to change. That afternoon he asked himself another question: If someone else were making the decisions I've been making for my business, what would I challenge them about? He knew immediately. You keep saying you want something different, but you keep making decisions that preserve exactly what you already have. Fionn sat with that for a while. It wasn't particularly comfortable. Good self-coaching questions aren't always comfortable. Self-Coaching Through Good Times and Challenging Times We often think we need to question ourselves when we are confused. When two choices seem equally possible. When something has gone wrong. When we don't know what to do. But sometimes the thinking that most needs challenging is the thinking that feels completely reasonable. This can be particularly important when you work for yourself. Freelancers, founders, consultants and independent workers make decisions constantly. Which clients to take. What to charge. Where to spend time. What to stop doing. Which opportunities to pursue. What kind of work to become known for. When to take a risk. When to protect what they have built. Independence gives us the freedom to make those decisions. But freedom from someone else's judgement also means freedom from someone else's questions. Without noticing it, we can become very good at explaining our own decisions to ourselves. Self-coaching introduces some friction. Not endless self-doubt. Not questioning every instinct. But the willingness, occasionally, to interrogate the thinking underneath a decision that feels obvious. Being a Good Boss to Yourself Fionn didn't turn the project down. But he didn't accept it as it had been offered either. He went back to the client and proposed a different arrangement. A smaller role. Fewer days. A narrower scope. The client agreed. The fee was lower. For the first time in a long time, however, Fionn had deliberately left space in his working life rather than waiting for space to appear. He knew what he wanted to do with it. The new service. The organisations he had kept meaning to approach. The writing he had kept fitting around everything else. None of it was guaranteed to work. That was uncomfortable too. But Fionn had finally recognised something about being his own boss. Being a good boss to yourself isn't only about trusting yourself. It isn't only about giving yourself permission, backing your judgement or having the courage to make your own decisions. Sometimes it means challenging the person making those decisions. Especially when that person is you. Because when you're your own boss, nobody else is responsible for asking whether the decisions you're making are taking you towards the working life you say you want. That question belongs to you. And sometimes, so does the challenge. CLOSING That's today's WorkLife Story — Self-Coaching When You’re Your Own Boss: Who Challenges Your Thinking? Fionn hadn't been making bad decisions. He had been making sensible decision after sensible decision. The problem was that collectively, those decisions were keeping him in a working life he kept saying he wanted to change. And perhaps that's one of the most important roles of self-coaching when you work for yourself: not questioning every decision you make, but knowing when your own thinking needs to be challenged. You can continue exploring Professional Self-Coaching through more stories and practical resources at School of WorkLife. All the details and links are in the show notes. Remember: being a good boss to yourself isn't only about trusting your judgement. Sometimes it means challenging the person making the decisions. Especially when that person is you. Thank you for listening.