The lonely freedom of working at home – Trajan King

The lonely freedom of working at home

My father-in-law is the Insurance Commissioner for our state. At a dinner last year he was telling me about the Governor’s new initiative to encourage more state workers to work from home.  He’s in charge of a pilot program for his department and is surprised by the initial results. The realities of working at home are not what was expected.
The department offered anyone who wanted to work from home at least one day a week the option to do so. Some took the offer but most didn’t, which was surprising.  In fact, one person started working from home a few days a week and after 3 weeks wanted to be back in the office. She said she missed being around people.
What people who have never worked at home may not realize is that it’s not easy. There are just as many or more challenges working at home as working in an office.
I worked at home for about 10 years and loved most of it, but it also has some considerable drawbacks and is not for everyone.


The freedom

Of course, the best thing about working from home is the freedom.  If you have a family, you are there for them. You won’t need to miss a soccer game, you can have lunch with your wife and your commute is about 30 seconds. Also, your kids get to see what you do for a living. You can turn that into a teaching opportunity and let your kids be part of your world as you teach them about careers and business.
The looks from neighbors when you go outside in your pajamas to get your mail at 2 o’clock in the afternoon is priceless. For years when I was working at home, my friends often wondered what I actually did since I didn’t go to an office and occasionally was found rock climbing or at a movie in the middle of the weekday. I loved the mystery!
That shorter commute also means you spend less on gas and car repairs, which is minimal when compared to the avoided anxiety that comes from sitting in traffic.  When I used to commute, I’d get home mad as hell a couple of times a week after an hour of stop and go traffic. That’s no way to live. While working from home, I appreciate the extra time I get to spend with my family.
No other success can compensate for failure in home. - David O. McKay Click To Tweet
In addition to the added time, you also save money in taxes since you can write off part of your house as an office expense.
That freedom allows you to set your own schedule. You’re the master of your time, which is very liberating and more efficient. It’s one of the reasons parts of the world are trending toward shorter workdays.


If you can work at home that means you can live anywhere. This is called “Geo Arbitrage.”  The average salary across the world varies greatly. Larger centers of commerce like New York, London or Hong Kong have a lot of high paying jobs but are some of the most expensive cities in the world.
Imagine if you could work at home with one of those high paying jobs, but instead of living in New York, you could live in Nebraska or Thailand?  High earnings. Low expenses.  That’s one of the ways people are able to save 50-75% of their income to become financially independent.
All the above advantages are great, but the one I like the most is the efficiency of working from home. Many corporate jobs require face time. I’m not referring to the iPhone app.  I’m referring to the ridiculous idea that you must show your face in the office during regular working hours, whether you have work to do or not.

The ridiculousness of Face Time

Face time was very common at the New York investment bank I worked at early in my career and I don’t suppose it’s changed much since. Often people finished their work and had nothing else to do, but wouldn’t leave the office until their workaholic boss did. Partly because they wanted to be there in case their boss wanted anything, which could be at 2pm or 8pm. They’d stick around with nothing to do – for hours. Day after day. That’s not satisfying work. It’s drudgery.
On the other hand, when you work at home, when you’re done working for the day, you get up from your desk and do something else.  No insane downtime! During the 10 years I worked from home, my workdays were usually 2-4 hours. A big reason is when I was working, I was 100% focused. There was no downtime chatting with co-workers, having long pointless meetings or entertaining vendors. I got right down to what I needed to get done that day and when I finished, I’d close my computer and go outside.



There is a downside to working at home. While it’s nice to have your office in the next room, with a short commute and the freedom to stop working when you’re finished with work, that convenience also means others will see you as always available. Your family may become a distraction, your kids may always be asking for a ride to ballet or to play basketball in the driveway (there are worse things).
My neighbors that knew I worked from home had a habit of dropping in to ask if I could help move furniture or watch their dog for the afternoon.  For some reason, people who don’t work at home don’t realize that you really do need to work. It’s not free time just because you’re in your pajamas.
It’s important to set boundaries when you’re at home. If you can have a separate office, the boundary is that office. When you’re in the office, you’re working and not available. When the door is closed it means, “Do not disturb.”
For some, the transition from office to non-working time at home is difficult. Without proper boundaries and a long list of things to get done, it’s tempting to keep working late hours, especially if you like what you do.
It’s also easy to be “always on.” If you work for yourself you know what I’m talking about. Your mind is always thinking of what’s next or an idea pops into your head.  When that happens it’s difficult to resist going into the office to take care of that thought, no matter the time of day. The simple task of starting up your computer to write down your idea or email a client takes you right back into work mode, so your brain never gets the chance to rest. Always being on is mentally exhausting.
I suggest when you leave your office you do a transition to change your frame of mind. Go for a workout or walk your dog. Give yourself a few minutes to get out of work mode and into a different mindset. During the rest of the day, if you get an idea or realize that you need to email someone, write it down in your “To Do” list for tomorrow. It can wait.


As I mentioned at the beginning of this article, working at home is not for everyone. That state worker who tried it only to come back to working in the office full-time did so because she got lonely. There’s nothing wrong with that. Some people are very social and really enjoy being around people at the office. They like people and the variety they add to your day.  They like the collaboration and the meetings.  It’s very difficult to collaborate and coordinate with people from home. If you’re an extrovert it may not be for you.
Recognize that working from home isn’t for everyone. If you have small kids it may be especially difficult. If you like being around people, you may miss that facetime.

How to have everything

So is there a way to have all the upsides of working from home and none of the downsides?  The goods news is there is a way!  If you’re interested in working from home or you already do, there are ways to manage it – to bend it to your will!
Set your boundaries. Set boundaries with your family, your co-workers, clients, and even your neighbors. Let them know your schedule and that this is how you do your best work.
Schedule everything. If you must collaborate or meet with clients, schedule it in advance.
Consider working from home just a couple of days a week and in the office the rest of the week. That way you get the best of both worlds. You get your productive time alone and the freedom of being near your family, but also get the collaboration and camaraderie of being with people at the office. If you work for yourself, consider a co-location space or starting a mastermind group to get some interaction.
Work with your company or manager to set up a schedule that will allow you to be most effective in your job while giving you the freedom you seek. You may find that companies are more willing to work with you than you may think, especially if you’ve proven yourself  a good employee.
Lastly, if you’re a student, consider the type of job and industry you’re looking at. Some are more flexible than others. Many jobs, like nursing or plumbing, require you be at a certain place every day, while others, like programming or web design, have more flexibility.
It’s human nature to think the grass is greener on the other side. We work in an office and wish we were at home. We’re at home and miss being in the office. If you can, try out different work arrangements to find what best fits your job and personality, be mindful of the upsides and drawbacks of each and hopefully you can find what works best for the life you want to create.

Who is Trajan King?

CFO & former Wall Street analyst helping your reach financial independence.

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Trajan King

Hey hey. I'm Trajan. I'm a minimalist entrepreneur who loves exploring the world (42 countries), learning new things (7 languages) and trying to get better every day (working on my backsquat).

I write about entrepreneurship and building an optimized and happy life through systems, good habits and scientific research.

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