Why Work-from-Home Jobs are So Freaking Hard and a Few Tips

I started telecommuting early, back in the late 1990’s, when it was still an experiment.

Large companies were looking for ways to reduce expenses and office space is a big one.  So, if your job didn’t require a presence in the office, (mine did not), they encouraged work at home.

They even set me up with an ISDN line, an early version of high-speed connectivity (I think it was a blazing fast 128K).

The poor suckers that couldn’t work at home were squeezed into 5 x 7 ft cubicles. Gotta save that space, even if you’re cramming people together like commuters in the subway.

Working from home was great. I  spent most of my day on conference calls, I could work in pajamas. Using a wireless headset, I could wander into the kitchen for coffee and snacks or go to the bathroom and never miss a beat.

I actually worked more hours compared to the old days when I drove to the office. That’s one of the risks of telecommuting, the office is only a few feet away, no separation between the job and your personal life.

My hours went through the roof and quality time with family went down. Not what I was expecting. Plus, the ease of access to the kitchen and constant snacking had the obvious effect, gaining weight.

Fast forward a couple of years—my employer made one dumb-ass decision too many and started their death spiral into dysfunction, layoffs and bankruptcy.

I was among the early victims, so I got a “package.” That’s corporate speak for a gift bag of benefits you receive as they kick your ass out the door.

Pivot #1


Joining up with a couple of other refugees from the corporate world, we started our own business. I continued working from home. The term telecommuting wasn’t too accurate since there wasn’t an actual company office. I simply told people I worked out of my home office.

I was reluctant to acknowledge this to customers, affiliates, bank officers and such. Turns out, it was quite common and my fears were unwarranted. Lots of “real” business is conducted from home offices.

Working extra hours in a start-up is the norm. So my work from home solution was ideal. I’m not sure how many hours I logged per week. No one kept track. It was basically:

Work – Eat – Sleep

This lasted for a few years until the business stabilized.

Eventually, our small business moved into a maintenance mode, the sales (and income) was lower, so it was time for another change.

Pivot #2


This time as a solopreneur, still working from home, Back to the Work – Eat – Sleep mode.

Unlike the earlier scenarios, I had no bosses to appease, no partners to debate every decision – it was me alone.

Be careful what you wish for—the solopreneur life can crush you.

Sure, it’s great to have the freedom to make your own decisions. But, that means EVERY decision, and a lot of them are big make-or-break decisions. Make the wrong choice and it’s it all over, done, stick a fork in it.

A small business needs most of the functions of  large business—just at a smaller scale. So, the solopreneur must act in multiple roles.

How Many Hats Can You Wear at the Same Time


  • Strategic Planning
  • Project Management
  • Operations
  • Accounting
  • Finance
  • Customer Service
  • Technical Support
  • Copywriting
  • Graphic Design
  • Sales
  • Marketing

Did I leave anything out?

Oh, yeah, one other little task: You need to actually create something people will buy.

So, how do you develop expertise in all these disciples? You try, but you can’t. You get good at a few of them, you’re average for the majority, and you suck at the rest.

How do you have the freaking time? You don’t. You imagine a magical device where you push a button and time stops for the entire world except you. And you leave it frozen for a week while you catch up.

You’re mentally and physically exhausted and you make a few dumb-ass decisions. It happens.

It’s not just me . . .

Other Work-at-Home Roles


  • Mompreneurs
  • Homeschoolers
  • Side-Hustlers
  • Digital Nomads
  • Multilevel Marketers (MLM)

How Do You Keep Your Sanity?


  • Work 80 per week, giving up all outside interests, friends, and family?
  • Over consumption of food or alcohol?
  • Performance enhancing drugs?
  • Go back to an office job?
  • Just slip into depression?

If you search on a term such as Tips for Working at Home, you’ll get advice.

Typical Work From Home Tips


  • Dedicated space
  • Good chair and desk
  • Get dressed for work
  • Set regular hours
  • Get plenty of exercise and sleep

There’s nothing wrong with these tips. But, they don’t address the more existential questions, such as:

How Do I Keep This From Destroying Me?


I’ll offer some tips. This isn’t based on curating all the content on the net. This is based on personal experience. But, undoubtedly enlightened by some things I’ve read from others as well.

  • Join or start a mastermind group so you’re not totally on your own
    • Ideally a group of 4-7 people with a range of experience, some with more and some with less than yourself.
  • Be authentic
    • Your clients and anyone you collaborate with can tell the difference.
  • Align 4 things
    • Beliefs, Thinking, Actions, Emotions
  • When to keep going vs quit vs pivot
    • How do you know when to keep going vs pivot or head back to a corporate job. A lot depends on your financial situation. But, it boils down to this: Are You Willing to Do What it Takes?

How Does This Intersect with Clarity?


Clarity is about a daily practice of clearing your mind, keeping focus and making good decisions. If you’re in a work-from-home role, these are all essential. No one else is looking out for you. You’re forced to be your own boss and you need to figure out how to be a good one.

If you want to learn more about productivity, clarity and habit formations,  try my free 14-day challenge.

If you want to speed things up and let me show you how all this works asap, enroll in the Clarity Course here and get a 50% discount.