I am finally taking a much needed vacation. I have not worked a full 40 hour week in 19 of the 29 weeks this year, so saying it is much needed is a stretch. I do not feel overworked at all, but a vacation is still a vacation and work is still work. For almost everyone, one is preferable to the other.

I reflect back on my working life sometimes and realize that it is going to take many years of working 32 or 34-hour weeks before I can average out over my career to a 40-hour week. I worked ridiculous hours for the first 12 years of my work life. I have worked two days in a row without sleep, I have worked Sundays, I have worked on planes, I have worked on vacation, I have worked on a laptop in a bar and I have worked while deathly ill. I have worked a lot.

I often wonder if I had turned my efforts towards entrepreneurial channels where I would have ended up. I also wonder if the effort piled into a corporate setting is the same as the effort I would pour into, say, my own consulting firm or being an independent contractor plumber. I suspect that if it is your own business you would expend even more effort on it. At the same time, I never felt in my early working life that there was any need to hold anything back in my ferocious non-stop pace. It did not enrich me except in the critical sense that it brought me where I am today (cushy-but-mindless high-paying consulting gigs). It took some life changes to make me back off my pace. Had I not met Bubelah I probably would be blogging right now from the Frankfurt Wi-Fi zone on my way back from a conference in Kuala Lumpur while nursing a martini to shepherd me through another four-hour layover.

I also wonder if, having stepped off that treadmill, I could ever recover the frenetic pace of my earlier career. Every day Little Buddy is a little more interesting and a little bit tougher to leave behind. I think taking a two-week business trip to Europe, as I used to do, would break my heart right now. I know people do it out of necessity, but I wonder what circumstances make people categorize things as necessities rather than people. If I needed the money to pay for health insurance, OK, I could do it. If I needed it to buy the new Wii, I couldn’t. I would reduce my lifestyle at this point to spend more time at home. I would have to be paid insane amounts of money to start working late hours and taking constant business trips, and insane money for me is really insane – “work two more years then retire” kind of money.

Nonetheless, I do have ideas for starting my own consultancy or online business or charity or small neighborhood coffee shop and on and on. I know that if I started my own consultancy I would be busy all day with client work and all evening/night trying to reach out to potential new customers. A coffee shop would open at 5 am and close at 5 pm. An online business – if it is going to be profitable – is a huge undertaking. A charity would involve long hours for little return. So the question I ask myself is “would this be fulfilling?”

I think the answer is yes. I don’t want to take long trips now because I would miss my wife and son, but a deeper reason is that I simply don’t care at all about “taking one for the team” for my clients. I suspect if I worked in a more entrepreneurial environment I would be more passionate about the work, so even if it meant long hours I would ultimately be happier and more fulfilled and that would make the time spent with my family even better. It might mean long hours in the near future but maybe – just maybe – it would mean a better future for all of us.

As pointed out elsewhere, the perfect moment to do this is not going to be announced by people yelling, “Surprise, this is it!” When I was 25, I would have sneered at the idea that there was a higher purpose than working insane hours in exchange for business-class tickets and luxury hotels and company-paid junkets to Budapest. I know now that I was wrong – the goal is independence to live your life as you choose, free from the tyranny of a paycheck.

I do still believe that moment will come when I will cast my status as an employee aside, and that is the first big step. And who knows? Maybe there will be fireworks.