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Finding My Path with SheSharp: Reflections on Career Coaching with Dina

Updated: Apr 5, 2023

This was originally posted on Gigi Kenneth's Medium Blog.

So here is a recount of how I tried career coaching for the first time… and I loved it!

But before I get into all that, you’re probably wondering what’s the difference between coaching and mentorship. At least I did because I usually saw those titles being casually tossed around in a lot of training programs.

But here’s the difference that stuck with me amongst the plethora of differences. Mentors are experienced individuals who want to offer a helping hand, and they do this by providing you with resources and advice based on their knowledge and experiences. I’ve been fortunate to have amazing mentors, I must say. Coaches, on the other hand, are trained and certified professionals who work with you to achieve a particular goal. I don’t know how other coaching sessions work, but this felt therapeutic as I had time and space to think and reflect.

How it all started? I found myself casually seated at a restaurant minding my business, surrounded by jollof and being a wannabe digital nomad when I got a Slack notification from SheSharp about free coaching sessions. Of course, I had to explore this.

The application was pretty straightforward, and I knew this was exactly what I needed because last year, I considered a career transition but was too scared to do it for various reasons (or excuses).

I’ve tried different career paths in tech, from software development, a bit of graphic design, cybersecurity, and Android development, but Machine Learning and Data Science have seemingly been the fields I’ve genuinely enjoyed, but I felt the need to try something new without letting go of AI.

Since I had some experience in the startup space and participated in training programs around entrepreneurship, I considered being a VC Analyst. My first full-time job exposed me to that a little bit (I worked at an accelerator). I’m currently taking a VC Analyst course for fun on EntryLevel, though. Some things you just learn to satisfy curiosity.

Staying on topic, I applied for the coaching program, and I think I was pretty vulnerable in my application. I’m not sure if that’s what helped me get selected or not, but I’m happy I made it through.

Before going any further, I must say that Dina Al-Alami is not just an amazing coach, you can tell from a conversation with her that she is a well-rounded and exceptional person, and I enjoyed every session out of the four we had.

She’s a trained career coach at Major Confusions, a coaching practice for mission-driven individuals and startups in tech.

Here's a quick recap of the sessions we had.

Week 1

We kicked off the call with intros, and I found Dina’s personal story really intriguing, how she moved from Jordan and figured out a career path that works for her. Then I introduced myself, and I realised I had a lot more to say than I thought. She was empathetic and listened to me all through.

This was the busiest week of all the weeks, to be honest, because I had to start from the very beginning and list out all the roles I have an interest in, industries I’d like to work in and values that are important to me. I listed my top five. And as I mentioned earlier, it felt like a therapy session with a lot of questions and self-reflection. Of course, you can clearly tell, the pro-con tables were my idea. I researched all the roles I was interested in and listed things that made me excited about them and things that made me uncomfortable about them.

In my notes, I mentioned how as kids, we’re used to having someone tell us what to do, and as adults, we’re presented with a plethora of life choices, and sometimes you just want someone to tell you what to do because it gets exhausting sometimes. Especially in those supermarkets with top to bottom shelves of different iterations of the same thing.

Well, with coaching, no one tells you what to do still😂, but you have time, a safe space and that extra support to figure out what you really want and eliminate choices until you find what works best for you.

Week 2

As you can tell, there’s less going on here. We did a game of elimination. Dina asked me to rate my excitement about each role I listed on a scale of 10 and discuss why (I felt like I was in an episode of the Anthropocene Reviewed with a 10-star scale instead of 5).

After rating and stating my reasons behind each figure, we landed on one career path that I’m willing to explore even though I’m part petrified, Product Management in AI, healthcare and social impact industries.

Then I listed a couple of skills I’d need to work on to be able to fit into the role, of course taking along my technical skills from data science and machine learning with me and my background in biochemistry. I mean, Jarvis has to be built somehow, so I can’t let go of AI. 🤷🏾‍♀️

Week 3

My focus for this week was tailoring my resume to reflect the career transition and pretty much everything else. Which I must admit was difficult to do, but Dina was really understanding and provided me with a lot of great feedback on how to tweak my resume and my portfolio page.

I had a mini existential crisis while doing all this, and YouTube’s algorithm suggested the right video at the right time. Tina Huang is a data scientist who’s worked at FAANG companies and shares her experiences as well as hosts regular live study sessions on YouTube.

Her video, Why You Will Pick the Wrong Career, was what I needed to see at that moment and helped me embrace the idea of changing, learning and growing.

Whatever I learn from this transition won’t be a waste because if it works out, awesome! If it doesn’t, I find something else and take these experiences with me. Either way, I’ll be fine.

Plus, this book by David Epstein is absolutely amazing, Range: Why Generalists Triumph in a Specialized World.

Week 4

No Miro board here.

We reflected on the past weeks and addressed my equal parts confidence, and equal parts fear while embracing a growth mindset, and discussed other fun stuff.

Final Reflections

I’m excited about this new AI Product Management journey and where it’ll lead me!

It was a wonderful experience having someone walk me through the thoughts I’ve been nursing for over 6 months, but I was too scared to make the change and wasn’t sure where to even start.

Part of this was my worry about what other people would think, but now I remind myself that people are too busy playing main characters in their own lives to care.

I’ve been doing a lot of learning and unlearning, especially letting go of self-limiting beliefs and building new habits. I’ve learned I shouldn’t be scared of change because it’s a regular part of life, and I should be open to trying new stuff.

The coaching sessions were wonderful, and I’d highly recommend having guidance from an expert, especially Dina.

I’m super thankful to her and SheSharp for the opportunity!


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