Navigating Boss Guilt: How to Recognise It & Break Free from the Cycle

blog Aug 07, 2023

Boss Guilt: What it is and how to break free as a leader

Are you a leader who feels like you can never get on top of things?

As the boss of my own business, I know firsthand what it’s like to burn the candle at both ends – and still feel guilty that you’re not getting enough done.

The other night I was exhausted.

I’ve been working long days. Not many breaks. Balancing the fine art of family alongside the demands of my business. I kept finding myself at my desk thinking, “If I just get this one thing done”, or “I’ll just do this one more thing before I take a break.”

And I caught myself.

This way of thinking signals the slippery slope of boss guilt.

What exactly is boss guilt?

The type of boss guilt I’m talking about is that feeling that you’re lacking, that you’re not doing enough, or being enough.

This kind of boss guilt can show up in the following ways:

Feeling like you should be working all the time – especially during your downtime;
Feeling guilty for prioritising your own well-being or taking a holiday;
Feeling like you’re not living up to your own or other people’s expectations;
Fear of letting yourself and others down;
Feeling the weight of self-imposed pressures to drive your businesses success and growth;
Setting unrealistic expectations (ambition and big goals are great – but not at the expense of your well-being);
Constantly comparing yourself to others in a way that negatively impacts your well-being.

Then there is the more complex, employee-centred boss guilt which can look like parenting / mothering guilt – where you feel the pull to attend to their needs immediately. This kind of boss guilt can show up when you find it difficult to make difficult decisions about your employees or contractors, when you feel the need to constantly say ‘yes’ to them and agree to things to keep them happy, even if it’s not in the best interests of the business.

There are a range of other ways that you might feel the insidious impact of boss guilt, and the first step is identifying it in yourself.

How do we know if we’re at risk of feeling boss guilt?

There are a few indicators that you might be at risk or already experiencing boss guilt. For the self-imposed type of boss guilt this might look like:

Exhaustion is one of the early indicators;
Self-doubt and second-guessing yourself;
Lack of clarity – struggling to see the forest for the trees.

The other type of boss guilt, the one where we constantly feel the need to please our team, can show up in much more specific ways including:

Feelings of resentment, anger and frustration;
Holding on to things, micro-managing and not delegating tasks;
Being overly critical of yourself and others;
People-pleasing and finding it hard to say ‘no’ to others;
Feeling responsible for other people’s happiness.

These behaviours also overlap with typical symptoms of burnout, so whatever the root cause, if you notice yourself feeling this way – it’s time to hit pause.

How to break free from the cycle of boss guilt

The power of hitting pause when you’re the boss is one of the most underrated and underutilised techniques among entrepreneurial leaders.

We get into business for many reasons, and the skills required for being a boss are often learned the hard way.

If you notice yourself feeling boss guilt, know that it’s possible to break free from this cycle:

You are not alone

As bosses, leaders, and entrepreneurs, it can feel lonely at the top. This way of thinking is a trap, though. Seek out peers, community, mentors, and coaches who can support you when needed.

Trust your instincts

Our bodies are more intuitive than we give them credit for. Tune into your body and trust your gut instincts, especially when all signs indicate you need a break, a reset or a reframe.

Get clear on values & priorities

It’s easy to feel like you need to do absolutely everything on your plate but accepting this is impossible allows you to get super clear on your values and priorities. This will enable you to make decisions quickly, conserving your energy for the essential things while limiting any angst over shoulds, clouds and woulds.

Set boundaries

It’s all too easy when you run a business for your personal and work time to bleed into each other till they become indistinguishable. Having clear boundaries around your work, with your work and with colleagues is the foundation of creating a healthy work ecosystem.

Structure your support

It’s one thing to know you’re not alone, but setting structured support for yourself means having regular support on the roadmap of being a boss and entrepreneur. This could be regular meetings with your business mentor or coach, joining a business goals group, or creating s support network.

Be kind

Beating yourself up as a boss can be par for the course – after all, the buck stops with you when it comes to pretty much everything in your business. But don’t forget to be kind to yourself and your employees. Being a business owner is hard. That’s why not everyone can do it. Being kind to yourself can be one of the most challenging things to do for yourself – but don’t skip it.

Boss guilt is a familiar challenge business owners and entrepreneur faces, but it doesn't have to be a perpetual state.

By recognising the signs of boss guilt, setting boundaries, and seeking external support, business owners can break free from this cycle and create a more balanced and successful business.

Remember, you are not alone in this experience, and taking care of yourself is essential for your and your business's well-being.

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