Deep Dives

Where are you Going? The Road to a Better Job Search

*Original post date – July 7, 2021.

Suppose you own a car and are interested in driving somewhere for a vacation in the near future. Most people would research where their destination is, determine how to get there and what to do upon arrival.

The following questions and answers would apply.

Who? – My spouse and I.

What? – A nearby vacation.

When? – A few months from now for a weekend.

Where? – Identify a destination.

How? – Driving directions. 

Why? – Rest and relaxation.

Career Planning is no more complicated than vacation planning.

Obviously, there is no need to list things out in this way when planning something small like a vacation since the process can be achieved easily and without little stress. The decision also does not carry much potential for added meaning, or long-term consequences.

There is little to no pressure involved, unless you and your spouse or planning partner don’t get along.

For a vacation, you just need to pick a place, find directions, and plan what to do when you get there. You may feel that individual career planning is much more complex and therefore very different but it doesn’t have to be that way.


The truth is that job searching works quite similarly to this process of planning a vacation. It is as complicated as you wish to make it. Instead of adopting a simple process to job searching, too many opt for the “hope for the best” or “bury the head in the sand” approaches, which are not real strategies. 

Let’s examine the most important questions from above as they relate to a job search.

Where?How?Why?
Vacation PlanningPick destinationFind driving directionsPlan vacation activity
Career PlanningChoose companies or clientsFind opportunity (through research and conversations)Plan career direction

Sounds simple enough, right? Well, like Warren Buffet’s advice about investing, this concept is “simple, but not easy.” Human emotion and behavior tend to complicate matters. There are many ways to get distracted.

  1. We Attach Meaning

There is no divine reason why you are or aren’t where you want to be but it is a human tendency to attach meaning hastily and to harshly judge ourselves.

  1. We Care what Others Think

Family, friends, and even media or celebrities can lead to a clouded view of what is reasonable, important, or even attainable for ourselves.

  1. Higher Education wants Your Money

With Federal Student Loans available in higher quantities to graduate students and powerful marketing campaigns, it can be easy to believe that a more advanced level of education is the missing link.

  1. We Doubt Ourselves

Just about everyone who has applied to jobs using Indeed’s ‘1-click apply’ method in an effort to save time by reaching as many companies as possible has struggled to gain traction. 

  1. We get Discouraged

Rejection, disappointment, or other events which lead to a lack of career traction often lead to a demoralizing feeling that prevents progress. When this happens, negative feelings overwhelm and questionable behavior often follows.


How do we achieve a realistic, positive mindset, that is capable of adjusting when necessary to remain on track towards success?

Achieve Progress

Nothing positive is generated from passive contemplation. To build momentum, confidence, and achievement we must take action. All of the below points of emphasis depend on an action-oriented mindset.

More than anything, these are learning objectives but they are ever-changing and evolve over time. Stay aware.

  1. Learn WHERE are you Going?
  2. Learn HOW to get There?
  3. Learn WHY you Care?

Seek and ye Shall Find

It must remain entirely your choice, and it should be decided through trial and error. Processes should only be implemented if they help you achieve the desired outcomes. Regular written reflection should become a habit to monitor progress and change course when needed.

The ‘process’ is always far more important than the technical tools used. However, becoming familiar with a combination of technology and systems that work best for you helps. Tools of organization such as a written planner, task list, Word Docs/Google Docs, spreadsheets, and electronic file folders should be utilized only if they work well for you.

  1. WHERE are you Going?

“Where do you go? Where are you going? Where? Well, let’s go.”

Are you an aspiring business owner, freelancer, or are you seeking employment somewhere? Just like planning a vacation, the first step to any endeavor is to choose some possible destinations. Which companies or clients would be a good fit for your interests and personality? Which would find your industry experience and skills relevant? Which job titles do they have that look attainable for you?

Along the path, hints of the answer to this question will emerge. Often these hints are revealed through simple conversation. Keep an open mind, be curious, opportunistic, and learn how to ask the right questions. As a result, you will naturally build the right relationships. When you learn important information make sure you use one of the above pieces of technology to record it. 

Access it regularly. These are your directions to get to your destination.

  1. HOW to get There?

Where are you going? With your long face pulling down. Don’t hide away like an ocean.” 

Your quest is to discover where you will flourish most. It has been widely documented that most jobs are obtained through some sort of connection at the company, or referral source if we are dealing with clients. 

Inside information is always better than shooting resumes out at job descriptions that you happen to see. Where do the people you meet work? Where are they going? Do you want to go with them? Why?

There as many paths here as there are roads. Leave no stone unturned.

  1. WHY you Care?

“Where do you go? Are you looking for answers to questions under the stars?” 

The power of “why” should not be under-estimated. However for some, it is important to reign this question in because it can become consuming. Human beings have a tendency to attach meaning to everything. The movie ‘Jeff, Who Lives at Home’ is a great example of this. The main character lives alone and attaches meaning to the most random occurrences. Don’t be this guy.

Ask yourself the right questions. Only with the right inputs, can the right outputs come. Why do you want to be a _____? Why do you want to work at _____? Why do you want to work with _____? If it’s because of prestige and status, or money, be honest with yourself. Own it. For most people, finding a job that makes some money is of utmost importance, don’t go into debt chasing some vague dream without doing the research. 

Make sure what you want makes sense for the lifestyle you want.

Conquer Vagueness with Specificity

A list of companies or potential clients list is most foundational. Consider this as the equivalent of your vacation destination. There have been far too many career-minded professionals who cannot answer the basic question: Where do you want to work? 

Be specific. Do not just say, “I want to work in an office because I need a job, I’m getting old, and am tired of working on my feet. I’d really love to work from home.” Who wouldn’t want these things? They are so vague, that they are opaque and virtually impossible to act upon.  

Instead, you should be able to say, “I want to work at one of 4 mortgage companies within commuting distance and I would like to work remotely if possible. ‘ABC Mortgage’ is my top choice because I have a friend who completed a credential they have in a job description I just saw so I may have a better chance. I want to work at a mortgage company because I like details and would like to be a successful real-estate agent in the long-term.”

See the difference?


Direct Your Focus or Others Will do it for You

A steady focus in the most important aspects of your life is essential to career acceleration. Purchasing a monster truck to drive to your vacation destination would make no sense. Much of what people focus their precious time and energy on makes a similar amount of sense. Are you focusing on what matters most? If not, do it. Now. 

Just by doing this you will feel bursts of progress. Much like an athlete who is able to maintain a low center of gravity thanks to core and leg strength, remaining well-grounded against the constant winds of change and various emotions that you will face throughout your career offers the best potential for success.

Success is never guaranteed for anyone, however if you are specific in your aims, well-grounded, and opportunistic, you will be more likely to land in a better place.

One day you may even find that where you are going is where you belong.

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2 thoughts on “Where are you Going? The Road to a Better Job Search”

  1. This is well grounded advice.The most important bit of knowledge here is thought.It is the motivator here. Old saying “Look before you leap.”

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