After about eight or nine months spent working from home and about the same amount of time “playing house” I have come to the conclusion that the two are very much related.  Working from home is like raising a toddler.  In a word: challenging.

I know there are about bajillion articles out there about how to work from home, just as there are about a hojillion (which is larger than a bajillion) articles out there about raising a toddler, which I can identify closest to herding cats.  What sets this article apart from all of them is that I will talk about both.  At the same time.

Little kids thrive on routine.  Rather, if you don’t want to get run ragged by the seemingly endless energy of a child then you need to establish a routine.  Same goes for working from home.

When you work from home a strange phenomenon emerges.  Your friends think you sit around all day in your underwear surfing the internet; your co-workers think you’re available, ready, and willing to work all the time.  You get calls to hang out and run errands with your buddies (who can’t imagine that you might be busy) at noon on a Wednesday just like you get emails asking you to send over some file “ASAP” from your co-workers (who can’t imagine that you have a life) at 10 PM on Friday.

Balancing both is a tricky thing — it’s all too easy to get sucked into either world.  It’s tempting to postpone work for another time when you get an offer to do something fun during “work hours” just as it’s tempting to answer “just this one email” when you’re supposed to be spending time with the people that matter to you.

Just like the toddler, whose uninhibited world is awash with endless possibilities, you need some framework and structure to your day or else you might find yourself running around naked playing with toy swords when you should be eating your vegetables (or whatever the “mature” equivalent is to this).

Working from home offers remarkable flexibility, coupled with the fact that you never have to deal with rush hour traffic, which is nice.  It can be both a trying and rewarding experience, much like parenthood.  Yet while many of us will spend hours reading up on how to be better parents, we spend remarkably little time improving our own work habits.

Luckily for us, we have (hopefully) been prepared to overcome the obstacles of self-motivation and personal effectiveness by our parents, our schools, and our previous jobs.  We know when we work best, how we work best, and what “our best” is.  Being free from the cubicle empowers us to structure our workday around these three things.  But, as anyone who has seen Spiderman knows, “with great power comes great responsibility.”

I have found that if I want to take advantage of all the freedom that working from home has to offer, I have to limit myself in certain ways to ensure regular productivity.  I’ve already shared my system for doing this, as well as a decent starting point for the whole process.  But I’ll add to this a short list of some helpful hints and tips I’ve picked up along the way.

• Set yourself a daily schedule and keep to it.  Since no one will be watching how well you abide by it, you’ll have to find a system for staying honest.  I covered this in depth before.
• Find ways to want to get up and start your day so you can get to work earlier.  I find it helps me if I work out after I get up, but this can be anything for you, such as eating a hearty breakfast.  Remember that an added bonus to starting early is finishing early too.
• When you’re supposed to be working, say “no” to non-work requests that can easily be rescheduled later.  Flexibility is key here, because some things can’t be moved, and it’s very important to keep your work and your personal life balanced.  But remember that when you’re supposed to be working, you’re supposed to be working.
• Have an office and a work computer.  Do as much to rid these of non-work distractions as possible.  This will help you stay focused, as you will get used to working (not playing) when you sit down at your desk and turn on your computer.  Keep the online shopping and the funny pictures of cats for the family desktop.
• When you “leave work” — leave work!  If you don’t let yourself work constantly then you will force yourself to be productive in the times you are supposed to be working.  Again, a little flexibility goes a long way here, as sometimes an hour of downtime during a weekend can be a valuable opportunity to focus for the coming work-week.
• Use whatever productivity and motivational device you employed in school to keep yourself on track.  For me, this is making lists and checking things off.  For many, this may be waiting until the last minute to work “under pressure.”  If so, then set aggressive deadlines for yourself that you must meet to avoid procrastinating.
• Decide in advance on acceptable “break” activities, so that when you need to take one you don’t get sucked into something totally unproductive and time-consuming.  For example, I have several sites bookmarked that I like to read during lunch breaks that feature articles on a wide variety of topics in which I am interested, from business life to motorcycles.
• Don’t drink alcohol.  There’s a reason that you aren’t supposed to show up hammered to work.  In fact, it may be worthwhile to make a list of other things that shouldn’t be done at work that can be equally as distracting as booze, depending on the individual.
• “Show up to work” presentable.  I’m not saying you have to wear a coat and tie, but you should at least be ready to leave the house at a moment’s notice if required to do so, even if you will never be required to do so.  I find this helps me feel a little more like I’m “at work” even though I’m just in my office across the hall from my bedroom.
• Take note of what you’re doing and how it’s working.  Then always try to improve.  It’s always possible!

I hope this advice can help even some of the seasoned veterans.  You may ask why I’ve been so focused on productivity when writing for an entrepreneurial blog.  It’s because entrepreneurs often find themselves in working conditions outside of the norm.  Sometimes it takes a very concerted effort to keep our inner toddler in check and not run wild when there are companies to start and people to lift out of unemployment.

Parenting also is one of those things that you often cannot see progress on a daily basis.  Your “victories” are clouded in the muck of just doing the job of parenting.  It is often not until years later that all of your efforts are rewarded (think of your child heading off to college, getting married, or finding that first job).  The destructiveness of bad parenting is also not often seen until years later.  Neglectful or ambivalent parenting effort manifests itself years later when the child reaches adulthood.  But either good or bad, you often have a hard time seeing the effects of your actions.

This is where parenting and being a part of a start-up is parallel.  You often work day-in-day out without seeing the huge victories.  You are often so far into the muck of daily operations that you do not see your daily wins and losses.  You often can’t decipher if you are winning or losing.  It is not until years later, that all of those daily victories add up to an acquisition, IPO, or stable cash flow company.

So, the next time you see your child’s smile or satisfy a custom support inquiry, think about the connection between parenting and entrepreneurism.

Unfortunately, these thoughts may be the most destructive of any that an entrepreneur may have. At Wasabi Ventures, we are all parents. We all have children that we love and adore. We would do anything for them and often we wear the rose-colored glasses of parenthood that show everything our children do as wonderful. And as entrepreneurs, we also love and adore our “children”, i.e. our companies.  But these emotions blind us from always doing the smart thing. Turning down a lucrative acquisition offer because we don’t want to see someone else run our creation or changing direction as the company is bleeding cash are both examples of this misguided love.

Luckily, there are solutions to this problem.  Having a great advisory board is probably the best remedy.  These independent mentors and assistants are detached enough from the blood, sweet, and tears of running the company that they can offer clear assistance.  Great advisory board members should be like great friends or relatives who can give you feedback about your children.  Sometimes it takes that independent third party coaxing to choose the correct path.