Chestnut Street Inn

Fritter on a white plate, garnished with white sauce and herbs

Pros and Cons of Working From Home

Jeff has often joked with guests that we are retired because we don’t punch a clock or report to an employer anymore, although I remind him that he does in fact report to me but that’s another matter altogether. While it is a funny joke, it’s partially true and partially false. There are many pros and cons of working from home. Yes, we no longer operate under a typical 40 hour work week/9 to 5 format, but we certainly don’t work any less, and in fact may work harder. Working from home is awesome. I wouldn’t change it for the world. It means to a certain extent I create my own economy, my own destiny if you will. But it also means that to a certain extent we live and breathe by what our calendar dictates to us and that can be both a blessing and a curse.

Let’s talk about working from home as a general framework for making a living. Most people who work from home work on a computer. As long as that computer has access to Wifi, they can basically take their work with them wherever they go. What a liberating way of making a living! For us, however, working from home is a lot more literal in that our home itself IS our livelihood. We only make money when we are here physically attending to guests, so the typical flexibility of working from home doesn’t necessarily apply to us. That’s not to say that we don’t have down time, because there are certainly those times of the day between guests where we have the freedom to retire to our room, play with the cat and watch TV (or in my case endless hours of Celine Dion videos on You Tube), but we don’t have the flexibility of being able to take our job with us on vacation, for example, and still earn a living.

With that said, let’s talk about the pros and cons of working from home, and specifically of running a bed and breakfast.

Con: The calendar dictates not only what we do on a daily basis, but on a weekly, monthly and yearly basis as well. On the micro level this means that daily and weekly we have to plan around the calendar to make sure we get everything accomplished that goes into innkeeping, including shopping, cleaning, cooking, maintenance, answering emails and marketing. On a monthly scale this means we look at the calendar to make sure we plan what projects we can fit in and which we can afford based upon what our anticipated revenue will be. On an annual macro scale, the calendar dictates to us when we can and cannot take time off, which we always plan in advance. Impromptu vacations and get aways don’t really work for us. We usually have to book them well ahead to avoid conflicts with guests and upcoming reservations. This isn’t necessarily a con, but just something we are aware of and plan for accordingly.

Pro: Knowing that we live and breathe by the calendar and by upcoming reservations, we do have the option to decide to shut the inn down whenever we deem it necessary or feasible without consulting anyone else because, hey, we are the boss! So we are able to say, next January we will take time off to go visit family in California and next March we will block time off to visit family in Florida. Nobody is going to tell us not to and as long as we block these dates off of our availability well in advance it doesn’t affect any reservations. Unlike a normal job with paid vacations that usually only allow for one to two weeks of vacation time per year, we are not restricted by that kind of parameter. We can decide that we want to take more or less time off as finances and scheduling permit.

Con: Budgeting. Certain industries tend to operate along the margins more than others. Restaurants are commonly in this boat, but inns are also in this category. While we have pretty accurate spreadsheets over the last 10 years that give us an idea of what we can expect based upon trends for past business and potential growth/contraction, it’s not a guarantee. We don’t really know month to month what our occupancy will be or what our expenses will be. As occupancy increases so do our expenses, and then there are the things that happen that you didn’t necessarily expect to have to pay for. So to say writing and keeping a budget is tough is a huge understatement. We can and do factor in major expenses like taxes or remodeling projects and set aside funds when we have them to help pay for these, but there is that scary moment when you look at the calendar for an upcoming month and don’t see a lot of bookings and wonder “how am I going to pay for X?” It always works out but it is definitely nerve wracking.

Pro: The fact that we work from home and that our home is in fact our job means that most of our expenses are built into our place of employment. We don’t have additional utilities, mortgages or outside living expenses above and beyond the inn. Aside from personal credit/loans, travel and entertainment, all of our typical expenses are tied to our business.

Con: Unlike a private home, when things break at a bed and breakfast, you HAVE to fix them. You can’t let them be until you have the money to fix them. Guests expect the best experience they can have and that means you can’t let things fester. Sometimes that means maxing out a credit card or figuring out a loan, but ultimately, it does force us to deal with things before they become a bigger problem.

Pro: When that stuff breaks, the business absorbs the cost and it’s a tax write off. Win.

Pro: We meet the most interesting people who not only are fascinating to get to know, but who often become long time friends.

Pro: We get to work together.

Pro: No commute when it’s snowy or icy. I fall outta bed and I’m at work.

Pro: If we have a great month and there is extra money in the bank, we get to use it however we feel like it. If I want to go out to have a fancy tasting menu at Alinea in Chicago for $250, I don’t have to ask the boss if I can spend the money.

Pro: I get to cook for a living. Who gets to say they can do what they love and get paid for it? Me. That’s who.

Con: There are days where working with your spouse and being together 24/7 is a challenge. Even when you absolutely love each other and are best friends like we are, there are days when it’s hard to find your “me” space.

Con: We’ll never get rich doing what we do.

Pro: It doesn’t matter because we will always be happy. Love what you do and you will never work a day in your life.


That’s the crux of the matter. We do work really hard and we do have our challenges. There is no such thing as the perfect job or a perfect life. But to say that we love this life and have crafted a lifestyle for ourselves that we wouldn’t trade for the world would be an understatement. So sure, working from home has it’s pros and cons, but as long as the pros outweigh the cons, it’s worthwhile work indeed.

Chestnut Street Inn Fall

Chestnut Street Inn Fall


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