Instead of just ask­ing “Why me?” ask your­self these ques­tions to deter­mine if becom­ing an entre­pre­neur after you retire from your job is a smart move for you.


5 min read

Opin­ions expressed by Entre­pre­neur con­trib­u­tors are their own.


The fol­low­ing excerpt is from Rick Terrien’s Age­less Start­up. Buy it now from Ama­zon | Barnes & Noble | IndieBound

How do you know if start­ing a busi­ness is the right path for you? And how do you know when the time is right to lay the ground­work for the next chap­ter of your work life? If your answer is that you’ll fig­ure it out when you get there, then you’d bet­ter start fig­ur­ing it out soon. Cre­at­ing new income streams with a new enter­prise is entire­ly pos­si­ble, but it takes time and resources. It’s always best to start small, start slow and start smart—with some self-assess­ment.

When you ask your­self some sim­ple ques­tions about where you’ll be work­ing at 60 or 65, don’t see work as a bur­den to live through. See it as a path to lib­er­a­tion in the lat­er years of your life. Ask your­self:

  • Do you under­stand that stay­ing active and engaged is bet­ter for your health and longevi­ty?
  • Can you afford to invest a small amount of mon­ey to launch a new enter­prise?
  • Can you invest the time need­ed to plan, launch and grow a small enter­prise?
  • Can you work through adver­si­ty?

Start ask­ing your­self ques­tions like these now so you can get ready for a future that is bright with oppor­tu­ni­ty and resilience. Sure, it can be scary, but it’s much scari­er to have no answer the ques­tion “Where will you be work­ing when you’re 60 or 65?”

Read on to dis­cov­er some of the most com­mon ques­tions peo­ple ask when they’re con­sid­er­ing a new busi­ness adven­ture lat­er in life. They’ll help you take stock of your own sit­u­a­tion so you can make those first moves toward start­ing a busi­ness.

WHY ME?

Why is an age­less start­up right for you? When you con­sid­er your options, you’ll like­ly see that the ques­tion per­haps shouldn’t be “Why me?” but rather “Why not me?” Con­sid­er this:

  • You have skills and knowl­edge that have tak­en most of a life­time to accu­mu­late.
  • You have the time to build a new career slow­ly and thought­ful­ly that can reflect the val­ues you want to leave for those who fol­low.
  • You have net­works of friends, col­leagues and con­nec­tions and that are unique in his­to­ry.
  • You have the pas­sion to make a dif­fer­ence and time enough on the plan­et to not care what oth­ers think about you.

Why should you start a life of entre­pre­neur­ship at this point in the game? Your entre­pre­neur­ship self-assess­ment should be focused on how you want to con­duct the rest your life. When you ask your­self, “Why me?” and won­der if an entre­pre­neur­ial this path is right for you, here are a few ques­tions to guide that inquiry:

  • What goals do you have for your new enter­prise?
  • What parts of your life would you like your start­up to enhance?
  • What parts of your life would you like to keep sep­a­rate from your start­up?
  • How much mon­ey can you invest to launch your start­up? Make sure this is mon­ey you can afford to live your life with­out.
  • What in your per­son­al­i­ty is most pro­fes­sion­al­ly impor­tant to oth­ers?
  • Are there oth­er areas of your per­son­al­i­ty that you don’t want to expose to your cus­tomers?
  • What mile­stones in your work life can you high­light as impor­tant to your start­up?
  • Are you will­ing to share your work­load with oth­er pro­fes­sion­als (account­ing, tax, etc.), or do you need to do it all?
  • Are you good at meet­ing new peo­ple?
  • Are you good at lis­ten­ing?
  • Are you good at empathiz­ing with peo­ple describ­ing their prob­lems?
  • Do you have the per­son­al­i­ty that can see prob­lems as oppor­tu­ni­ties?
  • Can you refine your pas­sion or mis­sion into a sin­gle com­pelling sen­tence or two?
  • Can you describe who the cus­tomers for your future enter­prise will be?
  • What prob­lems will you solve for your tar­get con­sumer?
  • Can you moti­vate your­self and work inde­pen­dent­ly?
  • Are you com­fort­able ask­ing for help?
  • Are you will­ing to work out­side tra­di­tion­al work hours?
  • Can you learn to meet new peo­ple and insert your­self into new sit­u­a­tions?
  • Are you com­fort­able using social media, even at an entry lev­el?
  • Can you admit you don’t know some­thing when appro­pri­ate?
  • Can you learn from mis­takes and fail­ure and accept out­comes that aren’t per­fect?
  • Can you say no to peo­ple and projects that don’t fit your busi­ness mod­el?
  • Can you work in busi­ness with peo­ple you may dis­agree with per­sonally?
  • Can you be sat­is­fied with not being rec­og­nized as the smartest per­son in the room?
  • Can you work in ambigu­ous sit­u­a­tions, in which no clear out­come is ini­tial­ly vis­i­ble?

Take some time to jour­nal your answers to these ques­tions or cre­ate a work­ing doc­u­ment that you can return to lat­er and review your answers. You’ll like­ly find that the ques­tion of “Why me?” is a mul­ti­fac­eted one that touch­es on sev­er­al areas of your entre­pre­neur­ial spir­it, real­i­ty and world­view.

Old­er entre­pre­neurs can cre­ate sig­nif­i­cant val­ue for them­selves and their com­mu­ni­ties by focus­ing on the life skills and traits that got them here: com­mon sense, tenac­i­ty and a strong eth­ic of help­ing. You can apply your exten­sive knowl­edge of what doesn’t work to bypass entre­pre­neur­ial road­blocks. You have the time and resilien­cy to launch new busi­ness­es that may be slow to grow but rich in ben­e­fits. You don’t need imme­di­ate returns as many investor-backed star­tups led by younger thrill-seek­ers do. You pos­sess the self-dis­ci­pline need­ed to see tasks through to fruition. By this time in your life, you’ve like­ly fig­ured out what you’re tru­ly pas­sion­ate about and can build new enter­pris­es to serve those goals.  

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