How to be your own mentor And Level-up your Career

Industry- and Role-Agnostic Advice to Help you Grow

Originally published on February 2023, updated for relevancy in March 2023

I’m usually the mentor, not the mentee.

I’ve only had 1 mentor as an undergraduate student + 1 mentor as an early career professional (at that point, I was in the industry for about 2 years after after getting my PhD).
- - Thank you Alejandra and LeAnna! (I met both of them through two different, official mentoring programs.)

I’ve mentored 50+ data professionals and 50+ start-ups to date, either as a one-off or as part of a 6-12 month mentoring program. (I’m unfortunately not taking on more mentees at the moment.)
I've been fortunate to be surrounded by smart and talented friends and colleagues who’ve mentored me as a one-off.

Here are some strategies that have worked for me, on how to mentor yourself to grow your career.

I’ll assume that the reason you’re here is that either:

Your company does not have clear career paths (and if you’re not sure if that’s the case, ask your manager), and/or
You’ve been having a hard time finding someone to mentor you for the next 6-12 months.

Please note: There are many fee-based services, platforms, and communities out there. I'll only be sharing free and non-affiliated resources to help you on your journey.

TL;DR: To be your own mentor, you’ll need to do (some) research, (some) networking, and as-needed, fill-in gaps with one-off mentoring sessions.

Start with End Goal(s)

What are your goals/aspirations? Are you looking to grow in your career, establish a “personal moat”? Or do something else entirely? There’s no wrong answer here!

Think about what that would look like – and what those achievements would look like in the immediate-, the short- to medium- term, and the next 10-15 years. Ask yourself:

What would you like to accomplish?
What do you see yourself doing? (Or what role do you want to end up in?)
What you’d like to do more of? [Harvard Business Review]
What would you like to be known for? [Harvard Business Review]
What would you like your legacy to be? [Harvard Business Review]

Be as specific as possible here. Can you make it a SMART goal?

For example, in the next 5 years I’d love to do 2 things, which will help me get closer to a private board role at a HealthTech company:

Be an EIR at a mission-driven VC firm (that’s improving the lives of the average person), advising start-ups on how they can improve their product market fit by understanding and solving their customers’ pain points with the help of data, and
Join a company that’s improving the lives of the average person as (ideally) a board observer.

Work Backwards from End Goal(s) to Create Roadmap

Now that we know what end goal(s) we’re working towards, what do you think is the smallest step – that’s the closest to the end goal – that will get you to the finish line? Then the next closest to the end goal? … And repeat as needed, until you have an idea for what your next smallest step to try is, relative to where you are in your career journey now.

For example, for my EIR goal, I’m looking to doing:

Next smallest step: If I‘m semi-consistently sent portfolio companies to meet or do due diligence for, I’d be more comfortable inquiring about a future EIR role.
Next smallest step to get to (1): Do one-off mentoring of start-ups in a VC’s portfolio, or one-off due diligence of start-ups a VC firm is considering for their portfolio.
Next smallest step to get to (2): Mentor at accelerator(s) where target VC(s) tend to attend networking events and/or mentor themselves and/or invest in graduates of the program.
Next smallest step to get to (3) may be any of these 3 steps, done in parallel:

Mentor at accelerator(s) that start-ups in the target VC’s portfolio thesis tend to graduate from.
Get to know your target VC.
Research what qualifications target VCs look for in EIRs.

Next smallest step to get to (4): Research which VC firms have EIRs that also align with your mission. (This is my current step for this goal.)
Next smallest step to get to (5): To break into mentoring at a given accelerator::
- - Sign-up for their newsletter and watch for calls when it’s looking for mentors to their next cohort.
  - Ask someone in your network that’s mentoring at a given accelerator for an introduction.
  - (How I landed my first one) If you’re a part of any communities, not necessarily start-up communities, watch for announcements around applications into an accelerator, then reach out to the person posting the announcement to volunteer to be a mentor.
  - Please note: for advice on what to look for in an accelerator, please see this blog post.
Next smallest steps to get to (6): Mentoring/advising/consulting for a number of start-ups, so that you’re able to see emerging trends and patterns and be able to build expertise to mentor those in an accelerator.

Developing the Roadmap without a Long-term Mentor

Step 1: Research

If it’s not clear what that step is, because this may be the reason you’re looking for a mentor in the first place, I encourage you to try the following:

Research (for example, using LinkedIn) what skills/accomplishments do people in those roles have?
Review job descriptions for those roles (using Google, LinkedIn, Glassdoor, etc.), to see what skills, achievements, qualifications and/or requirements do companies look for, in these roles?
- - Bonus: Similar to advice I shared on the blog post on how to get your resume to stand out, try to read between the lines to try to uncover what strategic gaps/needs do the companies have for individuals in these roles?
Attend panel sessions, read blog posts, and/or listen to podcasts where speakers are people currently (or have been previously) in those roles, and they’ll be talking about their journey. For example, for those:
- - Transitioning from academia to industry, I recommend these (free) workshops:
    - - (free) Recording of panel discussion: Academia to Industry, hosted by Locally Optimistic (July 2021)
      - (free) GWiS STEMverse on March 4, 2023 (full disclosure: I advise the GWiS board)
  - (free) Becoming a first-time manager, "journey mapping", or negotiating: I recommend (free) workshops by Tech Ladies
  - (free) Breaking into VC: SoGal Foundation’s events on Eventbrite
  - (free blog) "Ask a Manager" Alison Green's advice for "How can I get a management job without management experience?"
Learn about industry trends and pain points; you might notice some common themes that you can bring to your current industry that you may not have thought of otherwise, which will help you showcase/demonstrate your leadership skills in your current/future role.
- - Matthew Grohman takes it a step further and recommends that if you "Want an unfair advantage in your tech career? Consume content meant for other roles"

Step 2: Evaluate

From everything that you’ve read and attended, what stands out about the role? Are there any common themes/denominators?

Now that you know what companies tend to look for, evaluate how many of those skills/achievements you have now, and identify the top 3-5 gaps. These will be the stepping-stones on your roadmap to get you closer to achieving your goal.

Step 3: Iterate

Now that you know what gaps you’re trying to fill, or aspirations you’re trying to achieve, try the following:

(Easiest) Are you able to get this experience in your current role?
If that’s not the case, identify the one with the highest priority (e.g. most marketable skill). Do you have (some) bandwidth to fill this in on the side, potentially as "thought leadership" (such as by giving a talk, writing a blog post, doing a project, etc.) that connects to business impact/outcomes to showcase this expertise?
- - TIP: To make learning this skill more manageable, what’s the smallest thing you can do to show that you’re knowledgeable in this area?
  - For example, I help companies grow their business by advising them on how to implement real-time decision support with the help of ML/AI. Almost 10 years ago, to help me pivot from developing software from R to Python, I started consulting for a 2-person FashionTech start-up on the side of my full-time role in a completely different industry.
If you haven't worked at a very early-stage start-up before (with less than 6-10 people), and depending on your risk profile, would you be comfortable joining a start-up in a role that helps you fill-in this gap?
- - Jioana Zhang (JZ) did just that in her journey to a PM role, which she shares for First Round Review.

TIP: If you need a community to help you be accountable, ask your network for recommendations. If there isn't one that fits your needs, start your own!

Depending on the topic(s) you’d like to learn about, Learn Teach Code (where I used to be a volunteer mentor data science study group organizer) may be a great non-profit to partner with, for your community.

Organizing it can be as simple as making it a virtual get-together at a time that works for you, scheduled as a recurring calendar with a notification by email the day before and calendar notification 10-minutes before. (This is how I run the "Women on their Board Journey", a complementary community with quarterly virtual get-togethers.)
If you need an agenda (for non-study group sessions), I recommend the "lean coffee" format, for structured agenda-less meetings.
Bonus: By organizing a community, you’ve just demonstrated leadership skills! :)

After you’ve been able to patch one of the gaps, what’s the next most marketable skill (from your research) you should tackle next, similarly?

Please note: Depending on how long it took to patch the first gap, you may want to consider refreshing your analysis from Steps 1 and 2, to help you stay up-to-date.

Parting Advice

This will hopefully get you at least 50% there. To get you closer to your goal, now may be a great time to share your journey with your network, where you’re stuck, and what you need more support in; be as specific as possible. To make this a very quick (<5 minutes to reply), low-key ask, I would frame this as one of two-ways:

Sharing context around your end goal, what you’ve tried and where you’re stuck – and asking, either:
- - whom they’d recommend you talk to for advice.
  - what resource/small step they’d recommend you try out next, to get you closer to your goal.
Jules Walter on Lenny’s podcast shares an example (35:46 min) of questions he’d asked his network to help him be a better Product Manager.

Please note: unless you have a close relationship with the person, this may not be the time to ask someone you’ve met once, very briefly, for a (virtual) 20-minute (or more) coffee to learn about their journey.

Having said that, if you’ve followed the mentor’s advice – even if things didn’t turn out as expected, please feel free to give them an update, which will help you to continue building that relationship.

If you do end up asking for that quick virtual coffee, please, please, please send your questions ahead of time. This will help you stand out from all the other requests that they get, show that their time matters – and that no one else but them, is the right fit for this coffee.

Life happens! I also aim to give everyone an out; if someone is too busy to meet, I offer to discuss things async (say via email or a Google doc), and offer to touch-base in a quarter.

This shows that you value their time, you’re done your research, you couldn’t find these answers online, and the person is uniquely positioned to provide this advice! That's harder to turn down :)

As you go along your journey, remember what Miley Cyrus sings:

[There’s] "Always gonna be an uphill battle / Sometimes I'm gonna have to lose / Ain't about how fast I get there / Ain't about what's waiting on the other side / It's the climb".

Good luck!