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  • Writer's pictureSandipan Chatterjee

Secret strategies to battle common career shift challenges that may fail you.

Updated: May 20, 2023


Most people get driven by purpose or passion while opting for a career shift. I did mine, and it was not an easy decision.

I will share my experiences to help you identify the challenges and deal with them early to ensure that those do not become a trap for you when you are busy building your next career.

There is an easy way out to those hurdles if you trace those at the early stage and remain prepared mentally to deal with them.

Most fail as they are hard-pressed with drainage of funds, time, or lack of bandwidth. Intelligent people do enough planning before plunging into a new venture or something that is relatively new to them.

Initially, you will have all the excitement and grit; the critical factor is accelerating the pace and not letting the spirit subside.

I found that doing something new is relevantly easier than a decade ago; plenty of support, technology, knowledge, and references will not let you fail unless you decide to leave the driver’s seat.

Most feel that their field of expertise is saturated, and dealing with something new may ruin the prospect. Let me clear the air about this myth.

You will excel in exploring your niche when you design your offering focussing on solving the user problem and not keeping it generic.

Precisely, the concept of old wine in a new bottle is passe unless you propose compelling health benefits of wine that interest people & trigger a binge for more. Just a new bottle may generate curiosity but does not ensure sales conversation.

This deliberation is about two circumstances.

(a) when you decide to start on your own, either entirely by yourself or in collaboration

(b) you are advancing towards a ripe career and keen to have a CXO role in a futuristic allied industry.

Let me share the hurdles that you may encounter at the planning stage.




#1 When you market yourself, the most crucial factor determining your success is “why should people buy” your talent or your offerings.

Is there a compelling reason to buy your offerings, onboarding you for a top job, or pay for your services?

Most remain confused at this stage.

As you mature in your profession, you tend to manage a larger spectrum of operations; in a process, you may dilute your one unique skill or competence that may allure your audience.

You need to dive deep into your mind and find that one specialization. Let me share some examples; say, you are the head of Procurement of a company, and your specialization is Automation. I am not talking about ERP alone but using many other tools to project, predict and align teams for outstanding performance. So here your hook is Automation, as you could save time, energy, and money in the business with your unique skill.

If you can place yourself as a specialist with a proven track record and ability to churn a profit, people will be keen to hire you or your offerings.





#2 Next is deciding your path. People procrastinate at this stage for a long, and the career shift never happens. If your purpose is vital, I firmly believe you will sketch your path with clarity.

You will have this mounting block of inaction when you dribble with uncertainties to discover “What’s Next.” You can only break it by deciding.

A classic example of people with experience deciding on any career shift is fear of venturing into the unknown.

They are uncertain about sacrificing a cushy job till they are compelled to leave that or never fear venturing to learn new things afresh.

Like in any job, you always need certainty. Meet your target within a deadline, secure the promised saving in the budget, and show gains in number to prove that you have performed. You know this process; adopt the same actions for yourself.

For example, if you venture for a CXO role, plan how many target employers you like to reach out to, your communication strategy, metrics to check your growth of the network, etc. It would help if you built a solid plan for every stage to derive results. If you start your business, this strategy will be no different.

In the job, you will get replaced if you fail; you do not have a second chance in your self-employment either.

If you make mistakes, you alone need to bear the burnt.

Plan Option B is to remain on the growth path even with jarks & diversions.



#3 How strong is your financial backup? Let me break a myth here.

Shifting career is not an exotic vacation or doing a luxury detox session at a gurukul.

You do not always need to invest initially or are required to maintain a vast fund back up. Say you need to build on your public speaking and critical thinking skills when you eye for a CXO role. Please take it as an example. You may need to learn new skills to build on your competence and abilities.

You invest in courses & coaching to learn that help you succeed in your goal. When I turned into Career Coaching, I subscribed to some courses to learn marketing, personal branding, and technical training that helped me get more followers and sell my courses & services.

While you do that, plan for sustenance earning from your investment or pick up freelance consultations that feed you in the interim period till you reach your breakeven.

Many people take a sabbatical before starting their priced job with a new company.

Do not ever eat up your whole saving; there is a gestation period that you need to pass through. The more meticulous execution you do, your earnings will start early.



#4 90% of people are introverts in some way or another. Their personality is the biggest hurdle they face while networking.

Showing up in public is the fastest way to draw the interest of companies that hire you or speed up sales in your business. You have no second choice.

I have learned that no one else can network on my behalf except me. Again, one can use Automation, but technology lacks human-like proficiency to build the connection you require while networking.

There are ways to network. I have written blogs on Introvert Networking to share tips on networking from the background.

I was a victim of this hurdle. I could overcome it by convincing myself by saying, “I do not bother what people think,”

or “I can create content better than others. “Self-talking and believing in yourself will overcome this difficulty significantly.

It will help if you build an engagement plan and schedule while networking.

What value you offer to your audience will depend on how many people will follow you and get engaged with you consistently.




# 5 Organising yourself is an excellent strategy for success that most people ignore.

We spend 80% of our time on unproductive transactional activities and undervalue what our intelligent actions (20%) can fetch.

I was overwhelmed when I started my second career as a coach. Too many actions in diverse directions got me divided; this is most detrimental to progress.

You must focus on one thing at a time and finish it before picking up the next.

Attach more value to the quality than the quantity of work you do.

See, never forget that in your venture, be it shifting your career to a significantly higher role or starting your own business, you are the boss to do the review with you as there is no one else to poke you.

I follow this strategy; I keep it every Monday for the review with me. The list of work and metrics helps me with this review. What you missed to complete must be prioritized; otherwise, you will delay the milestones.

Most of us know what is good for us.

Normal human tendency is to build a castle of excuses for not doing something rather than mastering new-age weapons that win a battle in the world of competition.

Anything you never did takes courage, desire, and consistency to execute.

Building a second career or shifting careers for an exponential goal remains a far-fetched dream unless you believe, drive, and spend quality time with it.

There is no shortcut to success. Making the right decisions, trying even when you fail, and stop fearing are qualities that help turn any aspirational goal, like a career shift into a golden opportunity to shine & make your dream come true.

I am always there to help. Just reach out for Career Coaching, handholding, or learning career shift strategies.

Follow me on social media and visit my website www.curatescope.com for loads of free but worthy content.

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