For those of you who have never heard of the “Big Dig”, I learned about it in business school. I graduated before the project reached completion.

According to Wikipedia: “The Big Dig was the most expensive highway project in the U.S. and was plagued by escalating costs, scheduling overruns, leaks, design flaws, charges of poor execution and use of substandard materials, criminal arrests, and even four deaths. The project was scheduled to be completed in 1998 at an estimated cost of $2.8 billion (in 1982 dollars, US$6.0 billion adjusted for inflation as of 2006). The project was not completed, however, until December of 2007, at a cost of over $14.6 billion ($8.08 billion in 1982 dollars)as of 2006. The Boston Globe estimated that the project will ultimately cost $22 billion, including interest, and that it will not be paid off until 2038. As a result of the deaths, leaks, and other design flaws, the consortium that oversaw the project agreed to pay $407 million in restitution, and several smaller companies agreed to pay a combined sum of approximately $51 million.”

From my recollection in business school, the consensus was that at numerous times during this project it was evident that the costs involved did not outweigh the benefits. Since so many millions had been “sunk” into this project, those who were part of this project just kept on promoting it and wasting more money. Think about it, if your paycheck was coming from “big dig” funding then of course you would want the project to continue. One of the takeaways of this project is that people involved in this project should not have been the decision makers as to whether or not it should be continued. It was in THEIR best interest that the project was continued, not necessarily in the best interest of the city of Boston.

I mention this little story because I have seen so many people lose their careers to the “big dig” mentality. People invest so much time and effort in a particular career pursuit that they often fail to see that their money or time is not being well spent and in the end, they may lose everything that have invested into this project. Usually people sink money into degrees that are useless or people fail to walk away from a business pursuit when it is failing.


I was chatting with a woman who works for me and she was encouraging her boyfriend to go back to school and to get a second degree. She believed that having another degree will increase his chances of landing a job that he will find more rewarding than his current job. She thought an MBA was a good idea. I asked her what job she expected him to land with that degree. She didn’t know. This is was my point. If you do not know what you want to do, then how can you be sure that a specific degree will enable you to get that job?

In my opinion, if her boyfriend obtained an MBA without knowing what he wanted to do, it could easily evolve into a “big dig” situation. He could easily spend tens of thousands of dollars on a degree only to discover that he is either a) over qualified for positions or b) under qualified for positions and find that his degree has put him at a disadvantage for finding a job in general.

Think about it this way, say her boyfriend gets an MBA and discovers during his studies that he really likes marketing and wants to work in the field of marketing.  Then, upon graduation he starts looking for a job in marketing. He will not have any experience in a marketing position since he has yet to work in the field of marketing, so it will be impossible for him to find a job, because all but entry level marketing jobs require experience. However, since he has an MBA, employers will not consider him for an entry level job…and with his student loans, he probably cannot afford to work at an entry level job.

Thus he is stuck. He is overqualified for the entry level jobs and under qualified for more senior positions. He now has a degree, more student loans, and fewer job options. So…the question is really what do you do when you want to find a more interesting job? School is not the first option. The first choice is to research, research, and more research on possible career paths. You can either take a personal inventory of yourself first to see what careers may be of greater interest to you, or you can start with learning about as many career paths as possible.


If you take a personal inventory of yourself you start to see what you like to do in comparison to what other people like to do. Simple questions include asking yourself whether you like to do the same thing every day or if you enjoy working with people. For me, one of the reasons I abandoned the career path of teaching was because I couldn’t stand the thought of doing the same thing every day. It depressed me. I needed more variety in my day. A teacher’s schedule is very rigid and the more I spent time in a class room situation obtaining my undergraduate degree, the more I realized, I just couldn’t stand the idea of teaching.

To research as many career paths as possible start asking the people you know what they do for a living. How did they find their careers? For me, I had worked in marketing for about 5 years when I started seriously contemplating making a switch to accounting. I did like marketing. However, I had seen such turmoil in my marketing department and had worked with enough advertising agencies to know firsthand that marketing was a very volatile field. It was hard to find a job in marketing.

The people who were successful finding jobs in marketing often had worked for several different advertising agencies and held smaller rolls in marketing companies. Basically every two years they looked for a new job so that they could show that they had tons of experience on their resume and could eventually land a better job in the future. I knew that I did not want to try to find a new job every two years. Thus, marketing would not be a long time career path.

I also wanted a career that would offer a bit more flexibility. Through research, I learned that tax accountants that only wanted to work part time often just worked during the tax season—January to April. Since I eventually wanted a family, I knew that accounting would offer me more flexibility and even more job security than marketing. Thus, I decided to make the switch.


In America, we definitely live in the land of opportunity. Yet, so many people equate opportunity with demand. You can build any business that you want. However, a successful business is a product of demand. People have to need or want your goods or services.

Mr. Super Frugalette has discovered the show Restaurant Impossible. The premise of this show is that chef Robert Irvine strolls into failing restaurants with 10K and his knowhow as a chef and business entrepreneur  to help turn around these establishments. Time and time again, these restaurants are losing tens of thousands of dollars a month and draining family members’ life savings. The stories are so sad.

Chef Robert is able to salvage many of the establishments, but even watching the show, you know that some will not survive. The lost causes just never developed the clientele, location, or branding necessary to build a successful restaurant. Yet, the owners plow forward squandering more money and more time.

It is hard to walk away from a failing business. You cannot imagine having nothing to show for your time and financial commitment. You always believe that you just need one good client….and then it will begin to work out. Yet, all too often, this is not the case. The “client” either never emerges or does not produce enough revenue to sustain the business. Instead of accepting failure, more money and more time are spent trying to “grow” the business….


The biggest reason that people hold on to failing businesses for way to long is that they never planned an “exit” strategy.  For an exit strategy, you must determine which predetermined events will cause you to end your venture. Factors could include money, time commitment, client base, or the departure of key talent. Setting up these predetermined boundaries, eliminates emotions such as “gut feelings” or your enthusiasm and passion will equate to your success. Moreover, sharing these boundaries with a trusted confidant will enable you to be accountable for your boundaries and in turn help you commit to walking away from your failing business.

Readers, have you ever been confronted with a “big dig” situation in your life—something you knew you had to walk away from but found it nearly impossible to abandon the cause?

Photo: St. Bernard Burying His Tennis Ball, Sam.