When Is The Right Time To Start Again?



Have you ever found yourself in a bad situation?  The kind that had you scrambling for a way out, desperate for a fresh start.  It might be anything…a soul-crushing job, a draining relationship, or an environment that just feels wrong.

Usually by the time we think about jumping ship, circumstances are so complicated that it’s hard to decide whether to forsake our current direction for something different and relatively unknown.


Sometimes we stay long past the time to throw in the towel.


Remaining in a situation which no longer serves us permits all sorts of baggage to accumulate…physical stress, emotional wear, and even spiritual wounds.  Life’s little joys—meant to infuse our hearts with a lightness of being—are increasingly lost, day after day.  We can end up staying so long that pain and suffering become our baseline—we no longer even recognize the accumulating damage.  


Sometimes we abandon ship way too soon.


At other times we can be so adverse to feeling discomfort that we flee from situations at the first hint of trouble.  In the process, we discard potential experiences or relationships, which given time might have become quite precious.  Giving up easily means our strength and determination to succeed are never tested—we miss out on the gains, or at least lessons, of perseverance.


How then do you know what to do?  


Which choice is right for you, in this moment?  It’s one of life’s greatest and most perplexing questions:

“Should I stay or should I go?”

~ The Clash

Let’s examine a few clues to help you the best answer for your situation…  


Indicators that a fresh start may help

Starting line at a race


When your current path isn’t leading anywhere you’d like to go.


It could be a stagnant job that isn’t challenging you, a relationship struggling with the same arguments, or a project where you’re going through the motions to avoid having to say “I quit.”  

If you look to the future, do you envision a situation driving you in circles, without the potential for progress or transformation?  Since that’s one of our primary purposes in life—to learn, evolve, and share our gifts with the world—why cling to something that is weighing you down?

Check in with the following questions and notice what rings true for you…

  • Do I foresee any opportunities for growth or renewed joy regarding my current circumstances? 
  • Am I willing to keep putting my time, attention, and energy into this situation?



When a new direction is calling you.


Occasionally, life can be rolling along without problems or any sense of real dissatisfaction.  Then something new enters your life, and you know without a doubt it’s meant for you.  There’s an urge to go for it!  But doing so means giving up something else in your life to make space, which creates internal conflict.  

Dig deeper into whether to make the leap by asking:

  • Does this new situation bring me joy?
  • Is it reasonable to expect these feelings to be lasting or sustainable?
  • Am I willing to face the challenges that may accompany this new endeavor?
  • Can I acknowledge I will likely have to let go of something perfectly good, in order to have what’s exactly right for me?



When the effort required to overcome obstacles isn’t worth what’s waiting on the other side.


Sometimes a personal or professional challenge is surmountable, but it requires more of our time and energy than we’re inclined to give.  Perhaps the gains we expect to receive no longer seem as important or valuable in our lives as they once were.  

Consider in detail how much of your precious resources you’re prepared to invest:

  • Am I willing and able (physically, mentally, emotionally & spiritually) to dedicate my time and energy to conquer this challenge?  
  • Do I still want/value/esteem the goal on the other side of this obstacle?    


Despite circumstances being wildly different—the lure of a new passion or the demise of an old one—sometimes starting over is our best option.  By releasing worn out obligations, we open up space in our hearts.  And that’s necessary to grow our lives into the gift they are meant to be.  



Indicators that a fresh start might not help.

Running away from obstacles


When you’re running from what needs to be faced. 


I’ve certainly fallen victim to this mentality from time to time—thinking bright, new plans would absolve me from doing my inner work.  In reality, however, evading life’s challenges only kept me from learning how to step up and push through temporary discontent or stress.  

The short term relief of walking away from a painful situation isn’t worth the sacrifice of long term satisfaction from sticking with something that makes a real difference in your life.  So before you close a door on one aspect of your future, consider whether your reasons are simply fear of what it might take to get to the other side.



When you’re running from emotions that need to be acknowledged.


It’s difficult to set aside old anger or resentments when deliberating our choices.  However, resistance to uncomfortable emotions can lead to impulsive decisions—prompting us to give up on a worthwhile future because we’re still viewing it through a lens clouded by our past.   In the event that strong feelings are pushing you to walk away, allow yourself a bit of time to gain a fresh perspective.  

Additionally, get support if you’re having trouble seeing your circumstances with clarity.  This could be a conversation with a trusted friend or spiritual advisor, but in some cases deeper self-inquiry with a therapist might be necessary.  

The tendency to run from strong emotions and doing our personal work often overlaps, so I encourage you to ask the following questions if your reasons for starting over feel blurry.  

  • Do I still have a core desire to have this person or situation in my life in some way?  
  • What about this do I value, and how would it positively affect my life if I could overcome the circumstances that are weighing me down?
  • Am I feeling scared, uncertain, or incapable of putting in the effort to transform this challenge into a victory?  
  • Are these fears blocking me from taking constructive and necessary action?



When the obstacles will only follow you.


Sometimes our lives are beset with challenges that are out of our control.  For example, a chronic health condition might continue to affect your professional life despite switching jobs or even careers.  

At other times, our troubles pursue us through changes because we’ve failed to recognize our part in their creation.  If you are unable to accept and believe in your own worthiness to be loved, for example, a new relationship might never offer you the passion and companionship you seek. 

Failing to address these issues may mean your fresh start is doomed to become another stagnant and painful situation.  Before you make a life-altering leap, consider how negative patterns or unconscious decisions might be perpetuating your suffering:

  • How likely is it that my planned fresh start will wipe away all my challenges?
  • If any of the obstacles in my present circumstances follow me through this change, would I still want to make it?
  • What role might my own actions, thoughts, or decisions be playing in my current unhappiness?
  • Do I need to attend to these first, in order to give my fresh start the best chance of success?  


If you don’t stop and address the problems facing you today, they’ll only follow you into the future.  A new job or relationship won’t cure those feelings of “not enough,” which so often stem from inside ourselves.  It’s important to reflect on the various ways you might be avoiding the underlying causes of your unhappiness.  And acknowledge the possibility that starting over might not be the best choice.   



Can the need for a fresh start change over time?  


It’s never an easy process to start over, either in your personal or professional life.  That’s why considering a fresh start may need to happen more than once—because questioning a situation over time can lead to very different answers.

For example, there were several times during my martial arts training where I doubted my commitment and considered walking away.  One particularly challenging period occurred as I was approaching my candidacy for Black Belt.  The techniques were physically more demanding, my family obligations made it difficult to find time to practice, and quiet doubts about my skills left me dreading every class.  However, a little inquiry revealed that my thoughts of quitting were actually fears about claiming my own power and doing the necessary work—no matter how long it took or how many times I had to try.  Memories of tying on my black belt and shaking my instructor’s hand fill me with pride to this day.  

Several years later, though, another choice point on the mat led me to a different conclusion.  After attaining my second degree rank, I was struggling with nagging shoulder injuries and a growing desire to spend my limited time and energy developing my professional life.  Despite the loss of great relationships and a connected community, I made the decision to hang up my belt.  I kept my dedication to the meditative quality of movement-based forms by transitioning to Tai Chi, and opened up the space to pursue new passions.  

As you can see, similar impulses to wipe the slate clean with my recreational time lead to two very different decisions.  Each one turned out to be the best choice for that moment in my life.  Yet it was taking the time to question why I was contemplating a fresh start that led me to the right results.



How do you know if you need a fresh start?

woman contemplating a fresh start


When you’re staring down at one of life’s essential choice points, odds are you’re aware of it.  So this week, take some time to consider the questions in this free guide, giving yourself the space and silence to listen for what’s motivating your impulse to start over.    

Capture your thoughts in writing or a voice memo if that helps.  Talk it over with someone if the stakes are exceptionally high.

Sometimes, though, we don’t face an obvious fork in the road.  We just end up feeling a bit stagnant, like we’re going through the motions of life while missing something essential.  If that’s the case for you, take some time this week to evaluate your life from a broader perspective.  


On a scale from 1-10, rate your satisfaction with the following areas of your life:

  • Job/Career
  • Financial Situation
  • Health / Fitness
  • Recreation / Leisure
  • Relationships (Family/Friends)
  • Romantic Relationship ( Emotional & Physical Intimacy)
  • Personal Growth / Living Your Purpose
  • Your Mental/Emotional Health
  • Spirituality and/or Faith
  • Environment/Living Space


Consider mapping out your results with one of the many Wheel of Life resources available online for a clearer picture of where changes might add the most value to your life. 

Identify one area in need of improvement, and then ask yourself whether a fresh start makes sense for you.  



Maybe the answer is a resounding YES!  


Before you make plans or change direction though, I invite you to slow down and open your calendar.  Commit to a time of reflection, pausing to wait before taking action.  A few days might be enough for a simple decision like overhauling your closet.  But if the consequences of a fresh start are enormous (leaving a long-term career or ending a relationship), then you probably need weeks or months (and potentially some counseling) in order to feel confident enough to make a new beginning.  

In either case, schedule a future time to revisit the questions in this post to determine if starting again is your best option or if you’d rather keep working through your current situation.



Maybe your answer is No…or Not Yet.


We don’t always need a clean slate.  A little extra effort, a novel approach, or a bit of help can give us the push necessary to move past obstacles and claim our happiness.  So if you’re feeling ambivalent about a fresh start, take some time to investigate what is holding you back in this area of your life.  

  • What’s the ideal situation regarding this part of your life?
  • What’s stopping you from achieving that?  Externally?  Internally?  
  • What would you consider doing to create change?
  • What might you be willing to let go of, in order to move closer to what you want?

Starting over takes huge amounts of energy, so if you’re not absolutely sure that’s what you want, try applying a little effort to adjust your current circumstances first, and see how that feels.  


Free Guide for deciding when it's time to start over.

In either case, I encourage you to share this process with someone you trust.  Whether its your courageous plans to start over or your planned efforts to make incremental changes, we can all benefit from the wisdom of a shared perspective.

And if you feel inspired, leave a comment about your experience with starting over, or what area of your life you’d like to transform with a fresh start.  

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