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Exploring the human side of tech

My Career Transition into Tech: The Challenges of Choosing the Right Role

Chika O., April 21, 2023August 21, 2026

As someone who has had a chaotic career transition into tech, I can confidently say that it is not easy to choose a career path. Deciding to get into tech is the easy part. The growth potential and numerous opportunities that come with having a career in one of the most lucrative and seemingly laid-back fields are enticing enough. The hard part is choosing a career path that aligns with your skills, disposition and capabilities.

Initially, I was optimistic about a transition into Cloud DevOps Engineering. I enrolled in coding bootcamps and took online courses to acquire the necessary technical skills, of which coding and scripting were an important part. However, after many months of struggling, I realized coding was not my forte. In spite of my passion for tech, I was not understanding the lessons. Something about coding did not work with my brain, and learning became too tedious.

Determined to pursue a career in tech, I reassessed my skills and capabilities to find a role that best suited me. After researching and doing some personal assessments, I settled on Tech Support as the ideal fit for me. Tech support involves assisting users in resolving technical issues and providing solutions to common software problems.

I had already acquired a Google IT Support and a Microsoft Azure Fundamentals (AZ-900) certificates, in my quest to gain foundational tech knowledge. It was, therefore, easy to focus my strengths on what was working. I found that I enjoyed working with people and helping them solve their technical problems. My fashion background also comes in handy in this role, since I developed strong communication and problem-solving skills, which are essential in tech support.

Check out this YouTube series where experts talk about navigating their careers with the advent of artificial intelligence and emerging technologies.

To help you overcome the challenges of choosing the right tech role before transitioning, here are the steps you should take:

  1. Evaluate your current skillset against any tech career of interest: Start by making a list of the skills required for your career/role of interest. Whether you are a fresh graduate or an employee with years of experience, you have marketable skills and knowledge. Weigh those skills against the requirements for your target role. If you work in sales, some of that can easily transfer to a career in tech sales or digital marketing. The goal is to make your transition as seamless as possible. Don’t ignore any skills you already have that can make the pivot easier. This is also the assessment stage where you focus on your strengths and take note of your weaknesses.
  2. Create a list of your transferable skills: Don’t underestimate what you bring from your previous career. Skills like communication, problem-solving, project management, attention to detail, or customer service are valuable across tech roles. Identifying these helps you see where you already have a competitive advantage.
  3. Map a realistic path to learning the skills you will need on the job: Be honest about the time and effort required. Some skills come naturally; others don’t. Create a learning timeline that accounts for your current commitments and gives you space to experiment without burning out.
  4. Test before you fully invest: Before committing months to a particular path, do small experiments. Take a short course, work on a mini-project, or volunteer your skills. If coding feels like pulling teeth after a few weeks, that’s valuable information. You don’t need to fully commit to a path before knowing if it’ll work.
  5. Connect with people already in the roles you’re considering: Be it friends or people on social media, reach out to people already working in your career of interest. Informational interviews and conversations with them can reveal realities that job descriptions never will. Ask about their daily frustrations, what energizes them, and what they wish they’d known before starting. This will also help you check for alignment with the life you want and avoid burnout or future regret.
  6. Give yourself permission to pivot: A “failed” attempt isn’t wasted time. My detour through DevOps showed me my personal limitations, which was just as valuable as discovering what I can do. Building flexibility into your transition plan reduces the pressure to get it perfect on the first try.

In conclusion, making a career transition into tech can be challenging, especially with the plethora of paths to choose from. My experience transitioning from fashion to cloud engineering, and eventually to tech support, highlights how difficult it is to choose the right path in tech.

The list of challenges and how to surmount them is inexhaustive, and there are no guarantees that you will get it right on your first try. It takes a lot of self-reflection, research, and determination, including trials and errors, to find the right fit. But with perseverance, it is possible to make a successful transition.

PS: There is still some cloud in my career’s horizon, it just won’t be a straight path to tread. 

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Comments (8)

  1. Rahma Bilesanmi says:
    April 22, 2023 at 12:02 am

    Great article ! I agree with the challenges faced with so much diverse roles to choose from as one can easily get distracted and overwhelmed from lack of clear direction

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    1. Chika O. says:
      April 22, 2023 at 9:18 am

      Thank you, Rahma! And I couldn’t agree more with you.

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  2. Juan says:
    April 22, 2023 at 7:25 am

    Amazing 🤩
    I love the process too

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    1. Chika O. says:
      April 22, 2023 at 9:17 am

      You gotta love the process, it makes gold.

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  3. rose uzoeto says:
    April 22, 2023 at 8:47 am

    Yeah, transitioning into a new career path is quite tedious and requires lots of work especially for someone who has little practical knowledge of the new career. Kudos sis!
    I will be here cheering for you.

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    1. Chika O. says:
      April 22, 2023 at 9:16 am

      Thank you for the encouragement, Rose. It means a lot.

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  4. Bryan says:
    May 19, 2023 at 10:19 am

    Lovely feat from Seamstress to Techstress….keep up the heat.

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    1. admin says:
      May 19, 2023 at 11:47 am

      Serious Techstress😂😂

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