The Madness & Freedom of Working for Yourself

Seventeen years of self-employment has taught me one thing: working for yourself is equal parts madness and freedom. Some days it feels like feast, other days famine. And yet, I wouldn’t trade it for the world.

I could take a steady job, with the payslip, the pension, the clocking out. So why stick with a life that can be feast or famine? This post is about the daily tug-of-war between freedom and chaos and why, for me, the independence still wins in the end no matter the financial cost.

If you’d like to know more about how I ended up on this road in the first place, I’ve written a post with a little more detail here about why I’m still self-employed. Maybe it is worth a read too.

Flat vintage-style illustration showing a freelancer at a cluttered desk with papers flying and coffee, symbolizing the chaos and freedom of self-employment.

The PAYE Legacy

I’ve nearly always been working in my life. My first job came at the age of 12 — not exactly above board, but my parents gave me the nod and my first boss was accommodating. Those early jobs weren’t about money as much as they were about learning what work felt like, and they left their mark on me.

When I was working for someone, I never quite shook the feeling that someone was watching me, all the time, silently judging, silently critical of performance even if I never experienced any criticism.

This feeling even followed me into self-employment, it was that pervasive. Imagine, being your own boss and feeling that some invisible overlord was still watching you work. Have you ever had that feeling?

The Freedom: My Favourite Perk

These days, I'm a bit more relaxed about being watched or judged. I still get those feelings but I can laugh them off now. I don't need permission slips, no micromanagement, no clock-watching, no requesting holidays from HR only to be told you can't take that week off. I am still bound by all those business rules but I can decide when I fulfill, change or cancel them.

My most recent moment of autonomy was the creation of this blog during what would normally be a busy production and teaching time. I devoted a few weeks to getting this off the ground knowing the gain part would be a long way off and it was costing me dearly in the short-term. I decided that I was doing it and I changed my routine to suit. This is a decision that you really can't make as an employee.

More minor victories for me are the days when I decide, I've done enough by 4pm and I wrap things up. They don't happen often and I sometimes return to other minor duties later in the evening but it still feels nice to knock off when it suits me. I sometimes throw on a movie in the late afternoon on these occasions and switch off my analytical business brain for a while.

I can steer the ship wherever I like and that’s absolutely priceless at times.

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The Madness: Feast, Famine, and All the Bits in Between

The truth about working for yourself or the madness part that most business people won't tell you: the money isn’t steady, the sales aren’t guaranteed, you may be too busy for holidays. Like being paid regularly? You might have to skip your own paypacket now and again. Or even more often than that, such is the life.

Sometimes, you have a rough patch (the famine) followed by a very good week (the feast). For instance, towards the end of August just gone, lots of big bills to be paid and an empty looking bank account on the screen. I was very worried that I wouldn't have enough to pay the monthly business bills after a quiet spell and all of a sudden, the orders started coming in. For an entire week I had packages going out. Some of them substantial enough to give me a little cushion.

Ever woken up on a Monday and thought, ‘Will this week work out?’ That’s self-employment in a nutshell. There's never any definitive answer. Some months I wonder if I’m a genius or an idiot — usually both probably. It's really tough living this way but I think I'm fairly used to it now.

No Boss, but Also… No Backup

If you've never been self employed, you probably don't understand the complexities and nuances of working for yourself. You probably think something negative about your own boss from time to time because you don't understand why they do things the way they do. You might operate one small part of the business, imagine how it would be like wearing all the hats: customer service, packing, emails, ads, tax, stock, website, future planning. I could go on. I never considered what my bosses went through day to day, I bet you haven't either.

I regularly multi-task many difficult things at the same time even though my brain was never designed to do that but I’d still rather that than be told what to do by someone else. There is a sense of satisfaction if it all comes together in the end and you get it done.

This freedom means responsibility and that can be its own madness. You are on your own, with no backup. It's all up to you!

The Little Things That Make It Worth It

Small moments are all it takes to lift the mood sometimes. Little victories that make the war more manageable.

A week where I've had decent sales
An email from a delighted customer
An online Review that hits just right
The pride in a well-finished piece
A Student who manages a difficult instruction
A timely delivery of new stock to sell

These are some of the moments that balance the stress for me and brighten my day.

Would I Go Back to a Steady Job?

Sometimes I find myself daydreaming about a boss handing me my weekly wage, I still remember this sensation by the way. Steady pay, holidays when your request is accepted, switching off at the end of your day and not thinking about work until 08:30 the next day. Finishing on Friday for the weekend. Looking at the clock and wishing my life away....I remember it all.

Would I go back to it again — I don’t believe I would. I would probably last two weeks before a bosses habits or practices would annoy the hell out of me.

The hidden cost of working for someone else is always the same: your time isn’t really yours. The schedule isn't yours. The profits, if any are definitely not yours. I don't want to live with someone looking over my shoulder. I'm sure you can relate.

I think that the freedom to choose is more valuable to me now than the guaranteed cheque.

Conclusion: The Trade-Off I’ll Keep Choosing

It’s not easy. Some days I want to scream, to vent in someone's direction. Some days I want to pour a pint at 2PM and hide. I can't do those things, I have to soldier on.

I can choose to stay or quit. That choice is the freedom that keeps me here. I'm my own boss, I'm here for the good or the bad and I'm still going. I don't think I will get off this ride.

Self-employment is equal parts madness and freedom and for me, the freedom will always win

If you’re self-employed too, does this sound familiar? Leave a comment below if this strikes a chord.

Thanks for Reading,

David

About the Author

I’m David Condon, a blog writer and small business owner based in Tralee, Co. Kerry. After years of working for myself in woodcraft and teaching woodturning, I started this blog to share ideas, experiences, and finds that go beyond the workshop. From tech gadgets to life in Ireland, you’ll find a mix of personal stories, reviews, and opinions — all grounded in real day-to-day life.

If you'd like to know more, you can follow the link in the Note from the Author section below or visit my About Me page to learn more.

💬 Note from the Author
This post was written specially for David Condon Finds. If you enjoyed it, you might also like my other projects:

Phoenix DVD Blog – where I write about DVDs, Blu-rays, and life as a collector
David Condon Woodcraft – my main site focused on woodturning and handmade Irish pieces

If you’d like to support my writing, you can do so through the Buy Me a Coffee button below. It helps keep these side projects going — thank you!

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