What this actually looks like

It's Monday morning. You open the laptop and can't decide where to start. The client resources still aren't finished. Neither is the Instagram content, or the email newsletter you promised yourself you'd send every week. Maybe you need to redefine your ideal client again - the messaging still doesn't sound clear when you read it back. Who am I trying to help? How do I explain what I’m actually about? Everything feels equally urgent, so you open one tab, then another. Hours pass, and you’ve completed nothing.

Later you’re scrolling Instagram and see a coach posting client success stories, and making way more money, even though they started their business at the exact same time you did. The doubt creeps in before you can stop it: What am I doing wrong? Why would anyone work with me when they can work with someone more experienced? What do I even have to offer?

It’s exhausting.

How do I know if I’m second-guessing or being strategic?

Second-guessing is distinct from thinking something through. Thoughtful consideration weighs up information and arrives at a conclusion: you decide, and follow through on that decision, until new data gives you a reason to change your mind. Second-guessing is often fueled by worry and rumination: repetitive mental loops where you re-analyze past decisions without reaching a productive resolution, or imagine feared futures, like the consequence of making the wrong choice.

What looks like diligence, is often threat management. It shows up as:

• Procrastination and reassurance-seeking. Delaying making decisions, or asking a business coach or AI what you should do.
• Checking and rechecking. Re-reading your notes and references before making content, anxiously scanning for likes and comments after every post.
• Overconsuming information. Taking in more courses and podcasts that you’re not implementing, instead of taking action and iterating as you go.
• Worrying over judgment: Fearing what others think about your choices, feeling the need to prove yourself.
• Decision paralysis. Analysing so many options and outcomes that you become unable to choose any of them.

When coaches feel stuck, the first instinct is usually to go back to the drawing board: make another plan, research until you have an answer. It looks like thoughtful, hard work. Often it's a way to avoid the uncertainty of actually deciding, and what it would mean to put your work out there and find out.

The trouble with second-guessing is that it actively maintains the threat-system loop rather than resolving it, which is why more thinking about the problem so rarely produces relief from it (Gilbert, 2010; Kolts, 2016).

Once you notice you can't stop overthinking, that noticing tends to generate its own judgement: why can't you just make a decision, what's wrong with you, no one else finds it this hard, you’re pathetic. That criticism is itself a threat signal, so it feeds back into the same system that produced the original anxious loop. Trying harder to think your way to a decision usually backfires, because you're adding fuel to the exact state that's narrowing your thinking in the first place.

Why do I second-guess myself so much?

Frequent second-guessing is often the result of being conditioned not to trust your own perceptions. This can often be traced back to an early relational environment that was lacking in warmth and safeness.

We call this  social safeness The sense that you are cared for and accepted (Gilbert et al., 2009), which contributes to the development of a secure base: the inner freedom to grow and explore, free from the fear of making mistakes.

If you were criticised for being sensitive, for overreacting, or told to ‘stop making a fuss’ when you were visibly upset, you learn not to trust your own judgement. Often that means learning to disregard your body's signals too, because attending to them wasn't safe or helpful at the time. This can impair decision-making in adulthood and impact your interoception. Your ability to read your body's internal signals accurately, is directly linked to the quality of decisions you make under uncertainty (Price & Hooven, 2018; Werner et al., 2009).

Becoming a decisive business owner means reading what your own instincts are telling you, rather than outsourcing the decision to someone else or to more information. Without a strong internal anchor, a felt sense of your own judgement being trustworthy, it's easy to organise around other people's opinions instead.

Early relational environments that lack warmth and safeness don't just undermine trust in your internal signals, they shape the development of your emotion systems directly. The soothe system, which supports stress regulation, becomes difficult to access, while the threat system becomes sensitised (Gilbert, 2014). This makes the stresses of entrepreneurship harder to navigate, because the physiological state of threat persists for longer once it's triggered.

The entrepreneurship trap

Failures and self-efficacy. Entrepreneurship guarantees a steady supply of setbacks: a launch that flops, clients that cancel, building up the courage to pitch your services only to get zero inquiries. How you respond in those moments determines whether failure erodes your confidence or builds it. The instinct, especially if self-criticism is already your default, is to treat failure as proof that there's something wrong with you. As self-efficacy reduces, decisions become harder to trust, and you start to wonder if you’re cut out for this after all.

Isolation: Running a business alone affords fewer opportunities to access social safeness: the presence of affiliative and regulatory signals that modulate stress physiology through social proximity and co-regulation (Gilbert, 2024; Kelly, Zuroff, Leybman, and Gilbert 2012). A job supplies this by default. You have colleagues to joke around with, a manager who checks in to see how you’re getting on. Solo entrepreneurship lacks this, and support structures have to be deliberately built. Most business owners don't realise support is missing until they notice how much heavier every decision feels made completely alone.

Comparison makes this worse: Scrolling past other coaches who look like they're having easy success, especially while you're taking the slower, harder path because you've refused to lead with fat loss just to get clients, breeds a specific frustration: the sense that you're behind. Hustle culture turns that frustration into a story about how if you were really serious about building your business, you’d be working harder, resulting in you even more burned out and depleted. 

This is how coaches end up moving from mentorship to mentorship, or buying a program, following its framework for a few weeks, giving up on it, and buying the next one. It’s a predictable consequence of making decisions from a depleted, threat-activated state: the promise of structure, and the relief of someone else deciding offers immediate reprieve. The cost shows up later, when you spent a bunch of money and you're still no further along, because the inner foundations were never built. Outsourcing business decisions doesn't build the capacity that is actually missing: tolerance for deciding under uncertainty, and trust in your own leadership.

How to trust your own judgement

Self trust is the ability to believe in, and act on, your own judgment. Entrepreneurship requires tolerating ambiguity: you take action with no external feedback loop to confirm it was the right choice. Building self-trust means noticing when your mind responds to that uncertainty with worst-case thinking or self-criticism, and supporting those parts of you rather than fighting them, as you keep building the business that matters to you.

Limit external input. Reduce the amount of time you spend listening to business podcasts or consuming information, and create the space to listen to yourself first. 

Build your soothe system. The soothing system is built through regular practices that stimulate the parasympathetic nervous system, and it's associated with increased prefrontal cortex activity that inhibits ongoing threat perception (Armstrong et al., 2021; Gilbert, 2020; Petrocchi & Cheli, 2019). In practice, that's slower breathing before you open the laptop, a mindful moment in the morning rather than rushing straight into work, less time on screens and more time in nature, or an imagery practice that creates a felt sense of settling and connection in your mind.

Strengthen body trust. Start with external grounding practices that orient you outward, like a 5-4-3-2-1 exercise, or focusing on a colour you find calming. When that feels comfortable, you can try exploring internal sensations through body scans and mindfulness practices. One of the most powerful ways to build interoceptive capacity is through repeated experiences of sensitive co-regulation, being met and settled by another person, which is increasingly recognised as central to emotional regulation and the embodied sense of safeness (Filippetti, 2021; Murphy et al., 2017). 

Get support. Research on career insecurity suggests that having someone in your corner meaningfully buffers the psychological toll of professional uncertainty (Fu et al., 2026). Most coaches don't have this built into their work the way an employee with a supervisor does, so it has to be found deliberately. Importantly, this isn't someone who will tell you what to do, but someone who can help you arrive at your own answers.

Build a compassionate self-identity. Strengthen your relationship with self-doubt instead of trying to eliminate it. Compassionate mind training uses imagery practice for exactly this: embodying the version of you that's decisive, tolerates stress, and values rest as much as work. In entrepreneurs specifically, a brief self-compassion practice measurably lowered fear reactivity to a real business obstacle, without dulling their judgement of the actual risk (Engel et al., 2021), and self-compassion in entrepreneurship functions as a source of resilience to risk and failure (Allen & Leary, 2010; Chadwick & Raver, 2018). The version of you who runs a business well, and can meet anxiety with care instead of spiraling, is the most compassionate version of you.

Turn towards your fears. The part of you that's afraid to make a mistake, that worries your business will come crumbling down, that tries to manage what other people think, these are parts of you that need your support, not your dismissal.

How coaching helps

I know none of this is simple. Building a business already demands a lot of you, and it's harder still to navigate with a restless mind. In my experience working with coaches over the past seven years, what's typically missing isn't another marketing programme, it's tolerance for uncertainty and a compassionate relationship with yourself. You don't have to work that out through trial and error on your own business. Working with a compassion-focused coach gives you the structure and the supportive space to do that, without the price tag of a business mentorship attached to it. If you want to build the internal strengths that let you run a business well, Compassion-Focused Coaching For Business Owners is where that work happens.

Shannon Beer, nutritionist and body image expert with a diploma in Compassion Focused Therapy.