

Having worked for several companies/universities and then owning my own small business, I have had some time to reflect on my career and the choices I made. Although I would not call myself a career expert, I have learned some valuable lessons along the way. There are times in life when we have the luxury of choice and there are times when we do things out of necessity. Planning is key so that you have more control over your direction and the outcome.
While You’re in College
I recall being in a panic during my second semester in college because I had decided to major in Sociology after an amazing Intro class. What will I do with a sociology degree was all-consuming. Keep in mind the internet did not exist back then. I spoke to people, canvassed my professors, and searched my soul, but after months of panic, nothing resonated for me. Then one day while working on campus my, I saw a poster on a bulletin board and the title was: 100 Careers with a Sociology degree; I was elated to say the least. I thought about stealing the poster but my conscience got the better of me. I jotted down a number of career titles that seemed possible. I then set out to learn more about each of them.
At this point in my life, working for myself would never have been an option; I was lazy and unmotivated and way too insecure. My thinking was conventional and my dreams lacked possibilities. I mostly thought that I’d be lucky to finish college. I also wondered if anyone would ever hire me. Most of my college friends were far worse off in that they were even lazier. My parents were blue-collar and the word “career” had little meaning for them. Times have changed . . .I think.
Young people today seem to be much more aware of their options; I would even venture to say that many are fearless. People no longer think in terms of one job/one career. Moving from one job to the next is more the norm than the exception. I dare say that many young people today have their parents to fall back on. There are stats pointing to many living at home with their parents well into their late 20s and early 30s.
Endless number of resources on the internet:
Reasons to Run Your Own Business (click)
Out-of-the-Gate
I read and hear stories about young entrepreneurs starting their own business either while still in college or right out of college. I imagine some of these kids do it without even thinking too much about it. The world has changed and technology of course has everything to do with it. The absence of bricks and mortar make start-up costs far more affordable for tech entrepreneurs with a good idea. There is a lot to consider when starting your own business; I will share some of my own experiences later in this blog.
Your First Position
In my day, your first position was incredibly important. Where you worked and for how long mattered a great deal. Staying in one place for a few years was very important for resume building and to show stability. I’m not sure this is true anymore. I think it is more the norm to try new things and then move on to the next new thing. There was a time when individuals might work for the same company for 30 or 40 years; this is hardly the case these days. One big problem that I can see when considering changing jobs often, are the raises and promotions one might receive by proving oneself valuable to a company.
One of today’s considerations is that many of today’s businesses appear to have a revolving door policy: once an employee begins to become too expensive, companies often let them go and hire another employee at a lesser salary. This issue makes stability more difficult and mobility more prevalent. When you’re starting a family or caring for aging parents, moving from one city to another may be difficult — as I stated earlier, so much to consider.
I am a list-maker and I find it helpful to jot down all of the variables. What are your wishes, hopes, and dreams? What in your life is non-negotiable? Where do you want to live? What are your salary requirements? Is longevity important to you? Do you have a five-year plan? Can you put money into savings and/or a retirement plan (never too early to consider building retirement savings).
Owning Your Own Business
I had no choice but to start my own business. I was a high earner in New York and when I left to start a new life in Maine, I had a difficult time getting my foot in the door. I managed to convince a couple of big companies to interview me; however, as time went on, it became clear that I would probably not acquire the position I hoped for. I had a number of things working against me:
- I became too expensive for most companies
- Employers were afraid of offering me a job at a lesser salary, fearing that I would not stay long (they told me so). Career advisors told me to omit high level positions from my resume; something I just could not or would not do.
- When you’re over fifty you become high risk for companies offering insurance benefits. Older hires can raise premiums significantly.
- Many of the HR individuals doing the interviewing were in their 30s and 40s and could not relate to an older candidate.
- Ageism is alive and well in the United States.
I experienced one road block after another until I finally gave in and decided to start a consulting business. I thought that my expertise in hospitality could be an asset in a city that had a reputation for great food in a magnificent seaside setting (frankly the reason I relocated to Portland, Maine). Starting a business these days is not easy. After developing a business plan, developing a website was my next greatest challenge: cost, content, credibility, target markets, and time, were all major considerations. I had some savings put aside for survival in my new city and decided to put some resources toward my new venture. I was fortunate to find a graphics design students who was developing websites part-time. She was smart, talented, and her youthful outlook was exactly what I needed to offset my “older” perspective.
I never kidded myself about my age and what I knew and didn’t know. I bartered with my first few clients. I needed endorsements and a client list in order to garner any credibility in the crowded field of consultants. Initially, several businesses were very kind to me and open to giving me a chance. I learned some valuable lessons along the way:
- Don’t expect to make any money your first year (your expenses will outweigh your income).
- Keep track of every expense — tax deductions will become extremely important
- Be generous with your time and budget. I offered the first hour of consulting free and that turned out to be the cornerstone of my early success.
- Find other ways to supplement your income while you’re building your business. At one point I had three part-time jobs. All three were ways of meeting new people, attracting potential clients, and providing a distraction from the hardship of a start-up.
- Be careful not to burn out. I rewarded myself with some travel and nice dinners after each new client was signed on.
- Make sure your fees are competitive and fair. Offer clients an out and stand by your accomplishments. Don’t give away the farm; what you are offering is valuable.
- Your network is larger than you might imagine. Don’t be afraid to ask for help. Consider how much you help others and the joy that it brings you. Others will want to do the same for you.
Our Changing World
I voluntarily left a position when I was 54 years old thinking that with my education and experience, I was highly marketable; was I ever wrong. The world changed in the blink of an eye and I was so busy living life, I didn’t see what was happening in front of my face. We all grow up in a certain time and place where norms guide us. Change has always been a constant; however, today change is more rapid than it has historically ever been. Keeping up with change is an almost impossible challenge, but try you must or you will be left wondering why you didn’t. Never assume you know enough. Never assume that everyone around you has integrity. Be hyper aware without being cynical. Do your homework, ask a lot of questions, and keep up with technology.
Sometimes I have so much going on in my head and so much information coming at me, it feels like my brain is about to explode. I have learned how to store information on my laptop so that I don’t have to keep it in my head. Freeing up space in your mind will make it easier to allow new thoughts and knowledge to flow in. Meditation was a big part of my work life. I would close the door and free my mind of all distractions. This 10 to 20 minute almost daily practice would help me to gain perspective. Above all else be grateful that you get to choose. And never forget to thank those around you who have helped you succeed. Often we say thank you when it is too late. No matter how smart you or how resourceful you might be, you more than likely have cheerleaders: spiritual, emotional, and caring support and guidance that helps you navigate this changing world. Be gracious and grateful and good things will continue to come your way.
Follow Your Heart and the Money Will Come
Life is all about choices. When choosing working for someone else or having your own business, remember that decisions are often not etched in stone. Trying out an idea or pursuing a dream, doesn’t mean that you will be in it for life. Our fear of the unknown can be so strong it stifles us. Money complicates matters further. You know all the questions you ask yourself: Will I make enough to live on? Can I afford to send my children to college? Will I have enough for retirement. The questions can be overwhelming.

Where Your Career Takes You
People often think that owning your own business means that you no longer have to answer to “the man.” In truth, no matter what you do to earn money, you will always have to answer to someone. Restaurant owners answer to their customers/clients, as do plumbers, CPAs, lawyers, real estate brokers and so on.When you become successful and no longer have to be hyper concerned about earnings, you might be able to pick and choose your clients. I know very few business owners who can truthfully claim this position. Most business owners are beholden to their clients and in some ways, this can be even more stressful that working for someone else. When you’re an employee, because you do not own the business, you are usually not ultimately responsible for the business. You can always be held accountable; however, legally, the business owner(s) is responsible. You can be terminated, but it would be rare for an employee to be financially libel (there are of course exceptions). Most business owners carry insurance which should or could cover you up to a certain limit. It’s a good thing to look into before starting a position.
Big Lesson: If you go into business in order to escape working for someone else, you’re doing it for the wrong reasons.
Pointers Along the Way
- Stay true to yourself
- Weigh the pros and cons (make lists)
- Talk to people who have taken different paths
- Keep an open mind
- Consider your partner
- When do you want to start or family?
- Consider the lives of your children
- Have short-term and long-term goals
- Save and start a retirement plan early on
- Remember to enjoy yourself
- Be prepared for curve balls
- When you own your own business, you could easily end up working very long hours. It’s a good idea to plan your work day and try to stay on a schedule.
- Go on vacation; take time off
Last Words
One of my favorite questions is:
If you could do it over again, what would you change?
When I look at the decisions and choices I have made, I realize that although I did not love every job I have had, all of my life experiences seem to have led me to where I am today. Often we have no idea where a decision will take us; will it be the “right” job? Will I make a lot of money? Will it lead to a promotion? Will I like the people I work with? You can do a great deal of research and talk to many people about a company or business, but you cannot ever predict the future. So many things can happen along the way to determine an outcome. This is why it is often best to go with what you feel in your gut. If you have a support group around you and you work hard, you can weather just about any storm. Character building is just as important as career building.
One thing I might have changed was my appetite for risk taking. I’ve realized that times in my life when I threw caution to the wind, I had some positive results. I learned more about myself, I was prideful about the outcome, and I was often pleasantly surprised with the results. I was able to retire when I was 58 years old because I did a lot of planning. For me, leisure time, travel, exploration and enjoying every minute I have on this planet, have been my top priorities. Keeping your eye on the prize is essential for reaching your goals. Be flexible, be realistic, be daring, and be happy and as the experts say, “don’t sweat the small stuff.”
A number of you own your own business or may have thoughts about the topic. It would be great to hear your perspective.


