99 Questions - A Boomer's Primer For Surviving Transition

The word “crisis” suggests considerable pain and suffering. We all wince at the memory of the crises in our lives: having to choose which college to go to or career to start after High School, getting married, having a child, changing jobs, moving, divorcing, etc. In fact, the word “crisis” is derived from the Greek word “crisi,” which means decision or judgment. The times of our life that demand change and trigger transition force us to evaluate choices and make decisions and judgments. These crisis periods seem painful because they are usually forced upon us by circumstances we feel we cannot control. We are always more comfortable with the status quo we have developed and control. We have a natural aversion to the decision-making involving change. Many of us just don’t like to have to think ahead. But, in fact, the transition periods that confront us with life-altering options can be exciting and energizing. Evaluating our options is the first step in the progressive decision-making process.

Of course, we all know that past decisions that made sense short-term were not always the best ones long-term. But, no regrets. Bad decisions are better than indecision. We overcame all the crisis of the past, grew up, and survived so that we can face the crises of the future, making the short-term decisions that make sense now.

This primer is meant to provide Boomers facing retirement and other live-changing events with the tools to think about transition and making sound decisions that should last a literal lifetime. By designing this initial self-assessment as somewhat of a game, this is one crisis that you will probably have a lot of fun with. You are going to start figuring out who you are, where you want to be in 5 to 10 years, and how you want to get there.

RULES OF THE GAME: CHOOSE AN ANSWER THAT MOST CLOSELY DESCRIBES YOUR CURRENT ATTITUDES AND GOALS FOR THE NEXT TEN YEARS. THERE IS NO CORRECT OR INCORRECT ANSWER. IN FACT, THE MULTIPLE CHOICE ANSWERS ARE SUGGESTIONS ONLY TO GUIDE YOUR THINKING. YOU MAY CHOOSE MORE THAN ONE ANSWER. IT IS A GOOD IDEA TO WRITE IN YOUR OWN THOUGHTS NEXT TO THE ANSWERS YOU CHOOSE. AND REMEMBER -- YOU CAN MAKE A DECISION TODAY AND CHANGE YOUR MIND TOMORROW UNTIL THE CRISIS IS RESOLVED.

1. Are you planning to retire?
(a) Immediately
(b) In 1-5 years
(c) In 5-10 years
(d) I am already retired

2. What circumstance would trigger your decision to retire, if you have not yet retired?
(a) Involuntary decision: reach mandatory age/promotion limit
(b) Involuntary decision: poor health
(c) Voluntary decision: Miserable work conditions/horrid boss
(d) Voluntary decision: Want to enjoy the rest of my life while I am still “young” and fit

3. How would you describe your energy level as you face the future?
(a) High energy
(b) Strong, but with limits
(c) Pooped out, but can rally
(d) Burned out

4. If you know anybody who has already retired, how would you describe them?
(a) Happier than ever with their new choices
(b) Still vigorously exploring new options but nostalgic for the old status quo
(c) Proceeding in slow motion but moving forward towards change
(d) Depressed and miserable

5. How would you compare yourself to a friend or colleague who has already retired?
(a) I have nothing in common with him/her; my circumstances are different
(b) I have nothing in common with him/her, but I would have made the same choices he/she did
(c) I have a lot in common with him/her, but I would not have made the choices he/she did
(d) I admire the choices he/she made and hope to emulate the way he/she adapted

6. What would you like to do for the next ten years if you could?
(a) Keep working forever in what I know and do best
(b) Work part-time or volunteer, putting my hard-earned expertise to use
(c) Do something entirely different, develop new talents
(d) Take a break and do nothing but work on my golf swing and travel the world

7. What would you never like to do again?
(a) Work in a rat race
(b) Work for a rat under any scenario
(c) Feel financial anguish
(d) Have to keep a fixed schedule

8. How much free time would you like to have?
(a) Not much. I am happy when I am busy and productive
(b) It would be nice to have a little more time for myself
(c) Half a day free at least
(d) Free time all day long

9. Where would you like to live?
(a) Same house/ town, living on my own
(b) New house/town near my kids, parents, friends or relatives, living on my own
(c) Overseas, living on my own
(d) Senior community with all the amenities and future option for assisted living

10. How is your health?
(a) I eat right and work out every day
(b) I have a few foibles, aches and pains but take my meds
(c) I need to lose 10 pounds and take my meds
(d) I am a basket case and need to see a doctor

11. How is your stress level?
(a) I am in good balance
(b) I am stressed by big things affecting me (money, health)
(c) I am stressed by little affecting me (traffic, rude people on lines at the supermarket)
(d) I am a basket case and stressed by everything (world events, politics, environment)

12. What do you do to reduce/prevent stress?
(a) Adjust diet, exercise
(b) Sleep
(c) Make lists of priorities, things to do
(d) Seek empathy from friends or family

13. What is your attitude towards other people?
(a) I get positive energy from everyone and seek interaction
(b) I get positive energy from almost everyone and engage in relationships when approached
(c) Almost everyone saps my energy, but I engage in relationships when approached
(d) I mistrust people and would rather be alone

14. How do you assimilate information?
(a) Facts received first-hand
(b) Details researched second-hand
(c) Subjective assessment of patterns in the big picture
(d) Intuition into motives behind the events, facts

15. What is your attitude about your age?
(a) I am still a kid at heart and lie about my age
(b) I need plastic surgery and a hot sports car before I can feel better about myself
(c) I know a lot about a lot and demand the respect that I earned
(d) I am comfortable in my skin, sagging though it may be, and boast about my age

16. What is your attitude about your past?
(a) I am proud about who I am and what I have accomplished
(b) I have a lot more to do before I can leave the legacy I would like
(c) I could have done more and know there is always room for improvement
(d) I am a basket case

17. What is your attitude towards your future?
(a) I feel anxiety because the future is unpredictable and I can’t control it or adapt to it
(b) I feel anxiety because I am not sure I can adapt to the future
(c) I am confident that I can meet the challenges of the unpredictable future
(d) I am energized by the unknown and am having fun pushing my limits

18. What is your attitude about life in general?
(a) I love every minute of life and have suffered no major traumas, so I am ready for more
(b) I love every minute, but have taken a lot of knocks, so I am not that ambitious
(c) I have taken a lot of knocks and am just too tired to get back in the race again
(d) I haven’t done everything I wanted to, and I don’t see the point of all the effort any more

19. What is your attitude about death?
(a) Never think about it
(b) Know it is inevitable but don’t like to think about it
(c) Embrace religion and other spiritual guidance on the subject
(d) Draw on my optimism to fuel my energy level up and keep a smile on my face to the end

20. How confident are you in yourself?
(a) I have faith in a higher power to take care of me
(b) I have faith in myself to do what is necessary to find my way
(c) I have little confidence that I have the strength to do everything expected of me
(d) I am a basket case

21. What is your attitude regarding your significant other, if you have one?
(a) We are a team, in love forever
(b) We are a team, comfortable with each other, but the spark of love is gone
(c) We are at odds with each other
(d) I would be happier alone

22. If single, what is your attitude towards finding a significant other?
(a) I go out on dates and am looking for a permanent, meaningful relationship
(b) I go out on dates and am not looking for anything permanent
(c) I rarely go out on dates and, when I do, I don’t expect much
(d) I never go out on dates

23. How greatly does your significant other, if you have one, influence your decisions?
(a) We consult on everything and I take his/her ideas on board before deciding
(b) We consult on everything, but I make my own decisions in the end
(c) I make my own decisions without consulting
(d) He/she tells me what to do

24. Do you socialize with friends?
(a) All the time
(b) Sometimes
(c) Rarely
(d) Never

25. Do you go to meetings of any clubs/associations/church groups outside of work?
(a) Regularly
(b) Frequently
(c) Infrequently
(d) Never

26. What is your attitude regarding the younger generation?
(a) They know nothing and think they know everything
(b) They know nothing, so I want to protect them and teach them all I know
(c) They know a lot and I have a lot to learn from them
(d) I love their music, movies, and lingo and try to fit in with their crowd

27. What do you think about the younger generation’s work ethic?
(a) They are not as loyal to the employer as we were
(b) They don’t climb corporate ladders, but move from job to job to get ahead
(c) They won’t work overtime to get a job done the way we did
(d) They work just as hard as we did

28. What has your experience working with the younger generation?
(a) They don’t appreciate wisdom or training from veteran colleagues
(b) They didn’t seem comfortable socializing with veteran colleagues
(c) They are not as literate or polite as veteran colleagues
(e) They welcomed me in their group and were excellent colleagues

29. What do you think about working for a younger supervisor, if you did or might have to?
(a) He/she was a naïve jerk, so he/she deserved no respect
(b) He/she was a naïve jerk, so I was careful to humor him/her
(c) He/she was a naïve jerk, so I tried to provide guidance
(d) He/she was capable and knowledgeable, so I followed his/her guidance

30. What do you think about technology?
(a) I can’t live without my Blackberry
(b) I am used to a paperless office
(c) My vision is not good enough for me to use my Blackberry
(d) I print out everything and use my trusted agenda book and paper filing system

31. What is your attitude regarding children age 0-10 in general?
(a) They are spoiled brats
(b) They are bright but distracted by TV and consumerism
(c) They are receiving an inferior education
(d) They are angels

32. If you have grandchildren, what is your attitude towards them?
(a) They are spoiled brats
(b) They are bright but distracted by TV and consumerism
(c) They are receiving an inferior education
(d) They are angels

33. Do you have hobbies?
(a) Golf, tennis, gym, sailing, etc. that cost a fee
(b) Biking, photography, fishing, painting, etc. that does not cost a fee but costs equipment/materials
(c) Jog, walk, garden, etc. that does not cost anything
(d) Create art, pottery, sew, etc. that I can sell

34. Do you volunteer?
(a) Regularly
(b) Frequently
(c) Infrequently
(d) Never

35. On what do you base your decisions?
(a) Trusted logic based on facts or principles
(b) Trusted emotions
(c) Subjective projection of personal consequences
(d) Whatever is recommended by an author I read/TV personality

36. How open minded are you?
(a) Free thinking and spontaneous
(b) Change mind easily in response to new data
(c) Plan everything ahead of time, deadline oriented
(d) Judgmental regarding outcomes; don’t like surprises

THINK YOU KNOW ABOUT YOURSELF? LET’S MOVE TO THE NITTY AND GRITTY OF YOUR TRANSITION:

37. How would you describe your finances?
(a) I have plenty of savings, so don’t have to work after I retire
(b) I thought I had enough savings, but I am panicked by the economy and need more income
(c) I have some savings but some debt and need more income
(d) I am a basket case and need more income

38. What amount of savings, including IRA and 401K, do you think is enough to last you the rest of your life?
(a) $1 million cash for a couple, generating 8% per year = $80,000 before taxes
(b) $500,000 cash for a couple, generating 8% per year = $40,000 before taxes
(c) $250,000 cash for a couple, generating 8% per year = $20,000 before taxes
(d) $100,000 cash for a couple, generating 8% per year = $8,000 before taxes

39. How much do you think you will get in Social Security benefits if you retire at age 65?
(a) Over $5,000 per month after taxes
(b) Between $3 and $5,000 per month after taxes
(c) Between $1 and $3,000 per month after taxes
(d) Between 0 and $1,000 per month after taxes

40. Do you think you could live off Social Security benefits plus the interest generated by your savings without having to spend the principal?
(a) Yes, no problem
(b) Yes, cutting back on a lavish lifestyle
(c) Yes, cutting back on everything
(d) No way

41. If you don’t have enough, how do you plan to get the income that you need?
(a) I will rely on my children/expected inheritance to support me
(b) I will sell property and possessions to raise the money
(c) I need to work part-time
(d) I need to work full-time

42. Can you afford the rent/mortgage where you are living?
(a) Yes.
(b) Mortgage may adjust upward, putting me in a pinch
(c) Insurance rates and taxes may adjust upward, putting me in a pinch
(d) No. I need to downsize and move immediately

43. What do you expect your retirement benefits to do?
(a) Increase
(b) Decrease
(c) Keep up with inflation only
(d) Stay the same

44. What do you expect your investment income to do in the next 1-3 years?
(a) Increase
(b) Decrease
(c) Keep up with inflation only
(d) Stay the same

45. What do you expect your investment income to do in the next 4-8 years?
(e) Increase
(f) Decrease
(g) Keep up with inflation only
(h) Stay the same

46. Do you have enough health insurance?
(a) Yes, as a retirement benefit
(b) Yes, that I pay for via a group that I joined
(c) Yes, that I own individually and pay out of pocket
(d) No

47. Do you have enough prescription drug insurance?
(e) Yes, as a retirement benefit
(f) Yes, that I pay for via a group that I joined
(g) Yes, that I own individually and pay out of pocket
(h) No

48. Do you have enough dental insurance?
(a) Yes, as a retirement benefit
(b) Yes, that I pay for via a group that I belong to/joined
(c) Yes, that I pay out of pocket
(d) No

49. Do you have long-term health insurance?
(a) Yes, as a retirement benefit
(b) Yes, that I pay for via a group that I belong to/joined
(c) Yes, that I pay out of pocket
(d) No

50. Are you afraid to make mistakes?
(a) Always
(b) It scares me that I don’t recognize the mistakes that I make until it is too late
(c) I hate to look foolish, especially if I know better, but sometimes I get screwed by 3rd parties
(d) I recognize the mistakes that I make and try to learn from them

51. Are you afraid to break your lifestyle pattern?
(a) No. I am fearless
(b) Sometimes, depending how earth-shattering the break is
(c) Yes, until I get used to the idea
(d) Yes, always
52. How adaptable are you?
(a) I am very creative and adapt to anything quickly
(b) I adapt reasonably well
(c) I don’t like change at all, but I will adapt eventually
(d) I don’t adapt well

53. Do you think there is only one right answer to every question?
(a) Yes, mine
(b) Yes, when reasoned or argued well
(c) Rarely, since everything is relative
(d) Never

IF THE FUTURE LOOKS UNCLEAR AND UNPREDICTABLE TO YOU, YOU HAVE PROBABLY DECIDED TO LOOK FOR A JOB AFTER RETIREMENT AND THINK ABOUT WHERE AND HOW YOU WANT TO LIVE. THE FOLLOWING QUESTIONS WILL HELP YOU DETERMINE HOW YOU WANT TO PROCEED.

54. How do you gather career information?
(a) Websites, listservs, online groups, company research, job ads
(b) Libraries, books, print media
(c) Colleagues, friends, relatives
(d) Job fairs, job banks

55. What career information have you looked for on the Internet?
(a) Salary levels
(b) Career and labor market information
(c) Career planning, resumes, etc.
(d) Continued education and training, including business start-ups

56. What sources of networking do you have available to you?
(a) Professional meetings/conferences
(b) Colleagues
(c) Friends
(d) Relatives

57. Do you think you could ask your friend/colleague for a referral?
(a) No. I am too embarrassed
(b) No. I wouldn’t know what to say
(c) Yes. But it would be awkward
(d) Yes. No problem

58. What are your options for finding a job, given your experience and skills?
(a) Excellent. I could work tomorrow
(b) Good
(c) Fair. I have few transferrable skills
(d) Poor. I have no transferrable skills

59. Is there a market for your experience and skills?
(a) Yes
(b) Maybe, if I got additional training to become current in my field
(c) No
(d) I would have to research this

60. What type of organizations are appealing to you?
(a) Big corporation, like I am used to
(b) Small company, like I am used to
(c) Start-up, where they need me
(d) No organization: self-employed or sub-contracting

61. What training do you think you need for improving your human relations skills?
(a) Active listening and empathy
(b) Team building
(c) Counseling and guidance
(d) Motivation, mentoring, coaching

62. What training do you think you need for improving your counseling skills?
(a) Teaching and tutoring
(b) Creating learning environments and materials
(c) Illustrating concepts with examples
(d) Advocating for others

63. What training do you think you need for improving your leadership skills?
(a) Negotiating, bargaining
(b) Strategic planning
(c) Building team loyalty and inspiring others
(d) Making hard decision

64. What training do you think you need for improving your management skills?
(a) Organizing, establishing procedures and organizing structures
(b) Hiring, firing, Reviewing and evaluating
(c) Delegating responsibility
(d) Implementing policies with action plans

65. What training do you think you need for improving your communications skills?
(a) Public speaking
(b) Developing promotional and sales materials
(c) Writing reports/letters/talking points
(d) Interfacing with the media, advertising

66. What training do you think you need for improving your creative skills?
(a) Formulating
(b) Synthesizing
(c) Program or project design
(d) Visualizing

67. What training do you think you need for improving your analytical skills?
(a) Keeping track of details
(b) Reasoning and abstracting
(c) Prioritizing
(d) Interpreting facts for future action

68. What training do you think you need for improving your organizational skills?
(a) Computer training, word processing, database, graphics
(b) Time management
(c) Budget management, billing, invoicing, tax
(d) Cost analysis

69. Do you currently have a network to tap into for career guidance/job leads?
(a) No
(b) No, but I can look up things on the web
(c) No, but I can start compiling a list of names, phone numbers and emails of people I know
(d) Yes, I have already have a list

70. What type of salary do you expect to earn, if you were to find a job?
(a) Comparable to my last salary
(b) More than my last salary
(c) Less than my last salary
(d) I wish to volunteer

71. What type of benefits do you expect to receive, if you were to find a job?
(a) Medical, dental, 401K, stock options, life and disability insurance
(b) Medical, 401K
(c) Medical
(d) None

72. How would you like to portray yourself to a potential employer?
(a) Seasoned professional
(b) Casual professional/mentor/academic
(c) Genius with valuable insights
(d) Energetic, eager to learn new things

73. Do you have the wardrobe/accessories appropriate for the image you wish to portray?
(a) Conservative
(b) Contemporary
(c) Casual
(d) Unconventional

BEFORE YOU PLUNGE INTO THE JOB SEARCH, THE NEXT RULE OF THE GAME IS TO GO BACK AND LOOK AT YOUR ANSWERS. IT IS LIKELY THAT THE PRECEDING EXERCISE HELPED YOU TO RE-EVALUATE YOURSELF AND YOUR GOALS, SO TAKE THE TIME TO REVIEW WHERE YOU ARE AT.

NOW THAT YOU HAVE A BETTER UNDERSTANDING ABOUT WHO YOU ARE AND WHAT YOU WANT, GIVE THESE SAME QUESTIONS TO YOUR SIGNIFICANT OTHER, IF YOU HAVE ONE. COMPARE YOUR ANSWERS. YOU MAY WANT TO USE THIS OPPORTUNITY TO TALK TOGETHER TO BETTER DEFINE YOUR MUTUAL GOALS AND AVOID CONFLICTS BEFORE PROCEEDING.

IF YOU HAVE REACHED THE DECISION THAT YOU HAVE TO START LOOKING FOR A JOB AFTER RETIREMENT, ONE OF YOUR MAJOR CRISES IS OVER. IN ORDER TO FOCUS ON THE JOB SEARCH PROCESS, YOU HAVE TO ASK YOURSELF SEVERAL MORE QUESTIONS. THESE SHOULD TAKE SEVERAL HOURS TO ANSWER, SO TAKE THE TIME TO WRITE IN YOUR ANSWERS.

ONCE YOU ARTICULATE THESE ANSWERS, HOWEVER, YOU WILL HAVE THE BASIS FOR DEVELOPING AN UPDATED, GENERIC RESUME. YOU WIL ALSO HAVE DEVELOPED SOME OF THE TOOLS YOU NEED TO MAKE YOURSELF INTERESTING AND ATTRACTIVE TO FUTURE EMPLOYERS. YOU SHOULD RESEARCH EVERY JOB, AND REASSESSYOUR BACKGROUND TO MATCH THE SPECIFIC JOB REQUIREMENTS.

74. Are you familiar with techniques for resume building or interviewing?
75. Can you describe in ten seconds what your responsibilities were in your previous position?
76. Can you describe in two minutes what your major achievements were in your previous position?
77. Of those achievements, which would you like to highlight/talk more about?
78. What experience is relevant for the specific job you are seeking?
79. What are your relevant areas of expertise?
80. What are your relevant skills, on-the-job training, and experience?
81. What work-related training courses have you taken?
82. Did you ever receive an award/recognition for extraordinary service?
83. Which of your skills are transferrable to another position/company?
84. Did you ever solve a company problem or take charge in an emergency?
85. Were you ever in a position to create something and implement it?
86. Were you ever in a position to launch an idea and bring it to reality?
87. Were you ever a crucial team player for the success of a project?
88. Were you ever in a position to identify a need and meet it?
89. Did you ever contribute to policy development?
90. Have you ever increased sales or reduced costs in time or money?
91. Have you ever helped others to achieve their goals?
92. Have you ever improved efficiency or productivity of your work group?
93. If asked, have you suffered any failures? been passed over for promotion? had a problem with a supervisor or colleague? (These are customary interview questions, so be prepared for them.)
94. Why do you think you would be an asset to the company you are looking for a job with?
95. Since employers are scanning resumes, are you familiar with describing yourself in “key words”?
96. Do you have a list of three people who agreed to serve as a reference for you?
97. What are my transferable skills?
98. What jobs require or use those skills?
99. Where can you find those jobs?

CONGRATULATIONS! YOU WON THE GAME AND NOW HAVE SOME TOOLS TO COME OUT OF THE CRISIS OF THE TRANSITION. YOUR DECISIONS CAN BE TRANSLATED INTO ACTION. LET THE REAL GAMES BEGIN!

ONE LAST QUESTION: WHO ARE YOU GOING TO CALL FIRST?