Ask FM: Should I Pivot Into a Career In Tech? If So, How?

I have received several questions about how to pivot into a tech career. The draw of high salaries, flexible work schedules, and interesting problems gets people wondering: Should I break into tech? 

If they decide it’s something they want to do, the next question is how?

I received an e-mail from a reader wondering the same thing, and her story perfectly captures the essence of many others’ questions about changing industries mid-career. I’m going to do my best to answer, and then my hope is that you, fellow money mechanics, will provide your own experience, thoughts, and advice in the comments section. Without further ado, I will let Techquisitive introduce herself.

Dear Financial Mechanic,

I’m starting feel the pull toward a tech job, and thought you’d be in a great position to comment on my thoughts on a potential career change/shift, based on your unconventional job history. In particular, in your blog post about becoming a SWE with an ME degree you said,

“What is great (and terrible) about software development is that you are constantly learning what you don’t know.”

I LOVE that feeling, and in fact when I lose it in a role, it’s how I know it’s time to switch jobs!

About Me

I’m in my early thirties, a cis woman with a biomedical engineering BS, MBA, and PMP certification, living in the Seattle area, proud DINK with my husband (and we’re permanently childfree). I’ve worked in project management my entire career in various roles. I’ve never actually applied my biomed degree to any of my jobs, but employers are always happy to see it because it means I can understand technical concepts and/or learn them quickly.  I threw myself into the FIRE movement about two years ago, and now we’re about 4-5 years from retirement.

What I'm Looking For

I’ve always liked the “engineery” side of project management more than the softer skills – building massive, complex schedules, analyzing project inputs and data to distill down into important takeaways, resource planning, etc. I can get lost in that sort of stuff for hours. In my free time, I freaking LOVE travel planning (we do an international trip every year, and a few domestic ones) – itineraries, travel hacking strategies, etc. And of course, my FIRE planning spreadsheet is off the chain. 

The Blue Mosque of Istanbul from Techquisitive's travels

This all makes me think I’d be well suited for something related to data science and/or programming. My current job is also starting to get kind of stale, so it seems like a decent time to consider a pivot. The question is now do I start applying for roles I am presently qualified for and just keep doing the same thing, or jump into tech (which I have previously avoided). Since we’re so close to FIRE, part of me just wants to keep my cushy job and good salary and let it ride, but the idea of doing something more interesting for the next few years is also appealing.

My Qualifications

I’m getting my Scrum Master certificate in July, which I know will be useful if I want to move toward a project management job in tech. I also started with the Codecademy Python course (which I know just scratches the surface). Six years of my time at my first job exposed me to software development (C++), but all as a project manager managing engineers and suppliers. I also have a project at work right now involving some data analytics that I could use as a platform for a little Python project.

My Work Requirements

I do have a few job requirements, now that I’ve established myself in the work force and have lots to offer employers. 
  • I don’t want to exceed a 40-45 hour work week, with the caveat that I’d be more flexible on that if it was a virtual role (which would be awesome). Work/life balance is really important to me, and I’ve got a great thing going in that sense currently. Some stress and high workload at work is fine, but I want to be able to separate my work and personal lives.
  • Similar to #1, I don’t want to work for a “sell your soul/indentured servitude” company….*cough cough* AMAZON. I’ve spent my whole career at corporate behemoths, something smaller would be nice.
  • I make $127k/year total in my current role, which is I believe a little above average in the area per Glassdoor for my role and experience. I’d like to stay at or above this amount, to keep the FIRE train a-rollin’. I’m pretty sure I could do that, based on the cursory research I’ve done, but of course that isn’t the same as hard numbers from someone that’s been there.
  • I don’t want to leave Seattle – we own our house and are invested in the area.
  • I’m fine putting in some continuing ed work to make sure this is an area of interest, but not, like 2 years’ worth and/or thousands of dollars. I’m thinking more six-ish months. Again, being pretty close to FIRE makes me think signing up for a long-term educational endeavor at this point isn’t really worth it.

My Questions For You

  1. In your experience, could I find the qualities I’m looking for in low-level software engineering or technical project management role? 
  2. Should I target software engineering or project management? 
  3. How well should I learn Python or other languages before I start a job search?
  4. Have you ever worked with someone with more than a decade of job experience that suddenly pivoted to tech? 
  5. Any other thoughts or advice for me? 


Thanks in advance,


Financial Mechanic's First Thoughts

I am bowled over by Techquisitive’s thought and preparation– she is certainly not messing around. Many people mention that they would love to move into a career in tech but then bring up a hundred reasons why they haven’t, Techquisitive does just the opposite: she shows us that she is capable, qualified, and determined enough to make the switch.

There is a lot to dig into here, so I am going to go question by question.

Question 1: Could I find the qualities I'm looking for in low-level software engineering or technical project management role?

Let me be straight here: when I read the qualities that Techquisitive is looking for in a job, my mind went straight past engineer and bullseye’d in on project management. This makes sense because she is describing the parts of her own role of project management that she loves. As a software engineer however, most of those things (resource planning? massive schedules?) make me want to hand off the work like a baby with a stinky diaper and run for the hills.

I will back up a bit, however, to say that in the tech world often times the lines between roles can be blurred, especially in smaller companies. So before I say that the qualities of project planning, managing timelines, and strategizing sound a lot like project management to me, it is possible that as a software engineer you will be able to wear these hats as well.

As for Techquisitive’s job requirements, I think they are all possible in a tech role. The tech scene is booming in Seattle, with a slew of start-ups and smaller tech companies. I don’t think switching industries will require a move. If she decides to do software engineering and wants to take a structured bootcamp, there are several in Seattle ranging from 3-6 month timetables. I can check off each of Techquisitive’s requirements in my own software engineer career history so I think all of these are possible.

Therefore, my answer is yes, I think it is possible to find the qualities Techquisitive is looking for in a software engineering or a technical project management role. 

Not Techquisitive, but someone similarly interested in learning Python!

Question 2: Should I Target Software Engineering or Project Management?

With all of that said, Techquisitive wants to know which field she should really focus on. For that, I have some of my own questions:

1. What are you motivated by?

2. How much do you want to shake things up?

3. How do you want the next five years to look?

Techquisitive already has a lot of experience as a project manager, so I think translating those skills into a more technical role seems absolutely doable. However, is switching industries enough to keep her challenged if she continues as a project manager? 

Switching into software engineering will require more time and effort getting up to speed with new skills. Techquisitive expressed her love for learning, so the next five years could be spent taking on the complex world of coding, which she has dabbled in already. Is it worth the extra effort and frustration if she plans to leave the workforce in five years? I am curious why Techquisitive has avoided tech until now. What are those reasons and why did they change?

I would encourage Techquisitive to take advantage of the opportunity to take on the data analysis project at her current role. That is exactly how I got my first start into software engineering, a data analysis project using Python! By tackling the Codecademy courses and projects at work, she can decide if it’s something she would like to take on full-time. 

One caveat is that a junior software engineer will likely start out making less than $127k. Based on PayScale data, the average entry-level software engineer earns an average salary of $98k, which seems higher than what I would expect for a junior level position as it is. While that salary nothing to sneeze at, it is still a paycut for Techquisitive. I would expect her salary to stay about the same or increase if she transfers her current skills into an upper level Project Manager position. 

I don’t have an explicit answer to this question since it’s really up to what Techquisitive wants for the next five years. Technical roles can vary so much from company to company that it is hard to say which she should target. My advice would be to read job descriptions online of different roles, from project management, product management, scrum master, data scientist, software engineer, and whatever else pops up from there, and see which jobs hit those qualities you are looking for, regardless of job title.

Here are three examples I pulled from real job descriptions for roles in Seattle:

Data Scientist

Experience with one or more statistical analytical programming languages, including Python or R

Can use relational databases, including MySQL

Skilled at identifying analytic insight in data, developing visualizations, and presenting findings to stakeholders

Knowledge of object-oriented programming, including Java and C++

Project Manager

Experience with creating and managing to a project plan, managing resources, scope, schedule, and budget, and providing status reporting 

You are comfortable working under pressure and independently handling multiple projects and deadlines

 You are flexible and experienced with juggling multiple projects in a fast-paced environment

Product Manager

Experience influencing not only your own team, but also the company as a whole and external clients

You partner well with engineers and designers to conceptualize, ship, and iterate on products users love

You obsess over data and growth. You love digging into data and extracting meaningful insights to make smart product decisions

I already see pieces of these job descriptions that sound just like what Techquisitive was looking for, so I think she’s well-suited for a tech role, whatever the title might be.

Question 3: How well should I learn Python or other languages before I start a job search?

The answer to Question 3 hinges on the result of Question 2. If Techquisitive wants to pivot into a software engineer role using Python or another language, she should get the fundamentals down for a tech interview.

The Tech Interview

The tech interview is a multi-step process that generally goes like this:

  • The phone screen
  • Offline assessment
    • A take-home assessment
    • Solving a HackerRank or other puzzle
  • In person interview
    • Behavioral questions
    • Whiteboarding or live-coding questions

Coding will be a nice plus for a project or product management role, but they are less likely to grill you on how to traverse a binary tree. However, for a software engineering role Tequisitive should be able to solve a few different types of problems. 

How well should one learn Python or other languages before you start? You don’t need to be an expert. I have been a software engineer for almost five years and I still don’t feel like an expert. 

However, you should feel relatively confident to solve basic questions, and then start applying while practicing in parallel.  In my experience, once you start getting interviews, it gives the extra motivation to study hard the weekend prior.


You don’t need a CS degree to be able to answer these questions, but you do need to study. The best answers are ones where you can communicate your thought process as you organize your thoughts, walk through the problem, and optimize your solution. 

The only way to do this is to practice. I attended a software interviewing workshop on a Saturday, and the next Monday I used those skills in an interview. It taught me to slow down while my mind raced ahead, to communicate when I just wanted to write code, and make it through the terrifying moments of doubt. Without that practice, I might not have landed my current job.

Check out this comprehensive tech interview handbook, and practice until you no longer look at a question, go blank, and end up Googling for the solution right away. 

Other Resources

Techquisitive mentioned her start using Codecademy, which is awesome! I will also leave these other resources here for anyone interested in practicing for a technical interview.

  1. Leetcode and Hackerrank — interactive platforms for practicing coding interview problems.
  2. Cracking the Coding Interview — a book packed full of example coding questions.
  3. Daily Coding Problem — a mailing list that sends a problem a day.

Question 4: Have you ever worked with someone with more than a decade of job experience that suddenly pivoted to tech? 

On my first team, my coworkers had degrees in art, history, writing, and one had no college degree at all. Our Scrum Master had worked previously as a sports editor for the local newspaper. One of our recent hires just switched from being a teacher to being a back-end developer.

Then there are compilations like this one that tells the stories from 300 developers who got their first tech job in their 30s, 40s, and 50s.  It features Tara, who finished bootcamp and got her first dev job at 41, after switching from her job as assistant dean at a university and an English professor. 

Margaret says, “I got my first developer job a year ago this month. I’m 43. Worked in accounting for 10+ years and wanted a change after falling in love with programming. I’ve been going to school part time and studying via freeCodeCamp and others for about 4 years.”

All of this to say that it is not rare for people to pivot into tech after decades of job experience, and yes, I work with people who have done this. 

Question 5: Any other thoughts or advice for me? 

Techquisitive, you are on an impressive career track, with a fast timeline towards financial independence. With FI just around the corner, it is worth finding a job that is enjoyable and rewarding, potentially even one that you might not want to leave altogether. 

The skills you can learn from changing careers now could help you down the road on entrepreneurial ventures, pet projects, or part-time work, depending on what you want early retirement to look like. If you are starting to get bored in your current role, I think it’s a great time to pivot to a new adventure into tech.

One extra piece of advice would be to check out meetups and networking events for tech in Seattle. Meet people in tech and ask what they do in their role. 

Pivoting into tech will likely come with challenges, but we know Techquisitive welcomes a good challenge!

Money Mechanics, What Are Your Thoughts?

If you have made a big change in your own career, how did it go?

What advice do you have for Techquisitive?

Have you broken into the tech world? How did you do it?

Share in the comments below!

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  1. As I was reading this my mind immediately went to product manager! In my opinion, that type of role combines a lot of her previous skills/interests, without having to be TOO heavy on code experience. I’d also suggest identifying a few dream employers you have in mind and checking out the tech stack they work with. Learning Python is a good start, but if you decide you want to work for a small company and their main product requires, let’s say, JS and PHP, then you probably want to show some knowledge there. Just some ideas 🙂

    1. Yay, I’m glad there are a few other votes for product management! Good point about scoping out the tech before you get too deep learning just one.

  2. Great question and post!

    I recommend It helped me make my decision to switch from nonprofit to tech. Anyone (not just students) can get a mentor, and you can select from many different fields.

    My answer is yesssss tech is amazing. I finally get respect in my job, I finally have recruiters calling ME instead of the other way around. The perks are ridiculous. And I LOVE my job.

    But I’d hesitate to recommend it to Techquisitive given her salary reqs.

    Here’s my take as (I’m a software dev with 4 years’ experience, career switcher at age 29+):

    Entry-level you will make nothing near $127k, esp if you don’t have a degree, internship, or know a super in-demand framework.

    I knew the latest JS framework in NYC in 2015. I got 4 offers: $45k for a super new startup, $57k from a nonprofit, $90k from a fast-growing company (that seemed disorganized and involved uber overtime), and $65k from an ad tech company. I took the $65k and am happy I did.

    2 years later, I reached $100k.

    So yes, you’d take a MAJOR pay cut.

    That’s probably the end of the conversation.

    BUT Say you’re willing to take the cut:

    There is a lot of overlap btw project mgmt and software engineering, as Fin Mechanic pointed out. Both sets of people manage projects, need to be organized, both sets of people weigh in on how to make the product and making compromises.

    _Software dev job:_
    1. Requires a lot of preparation. I did 5 months of a bootcamp along with a lot of solo learning and studying for interviews. Even if you know the latest tech, getting your first job is still like pulling teeth.

    Throughout the next few years, you have to be humble yet not beat up on yourself. You are guaranteed to suck for 6 months – 1 year at your first job even after all that preparation, and not be amazing for a while after that.

    2. …is puzzle solving! This is what I love about it. I break big problems into tiny problems and tackle them one by one. If those kinds of tasks are less interesting to you, you will be unhappy for most of the day.

    Patience is a key skill for this job. That has been my biggest challenge. I easily become impatient, decide I’m terrible at the job and don’t belong in tech, etc whereas people who are the most successful just keep plodding and trust that they will find the solution.

    3. Is more solitary. I spend about 2/3 – 3/4 of my time puzzle-solving alone.

    One more thing — One thing I had to become ok with was having 23-year-olds as my mentors and teachers. And they had YEARS more experience than I did (at age 30). You might also have a boss who is in their late 20s, as the field skews young (especially in startups).

    _Project mgmt job_:
    1. Do you like negotiating and working with people? Are you a confident decision-maker? These are key skills for this job.

    You will be liasing between management, customers, devs, designers, and QA. You will be trying to make everyone happy and in the end make only some people happy. Unpopular decisions b/c of compromise. — (this is not just what I’ve observed, but what I heard from a friend who transitioned from software dev to project mgmt. He liked both jobs, for different reasons.)

    In sum, you have to have very strong people skills, as well as the emotional strength to go home from work and be ok with disappointing people some of the time.

    2. Similar to above, you have to be comfortable with meetings. Lots of meetings. Sometimes 6-8 hours a day. As an introvert, I find most meetings to be intimidating and am easily frustrated when my time feels wasted. A more patient and extroverted person would really enjoy this job, though.

    3. You will still have to learn some tech (databases and deployment tech is useful), but much less.

    And yes! If you work at a good company, you will be able to leave after 40 hours. Many tech companies value work / life above all.

    1. Ginna, you hit on some really great points here. Thank you for sharing your personal numbers, that always helps provide a bit more context! I think you did a great job of summarizing the different work-styles of the positions, and what to expect if Techquisitive decides to pursue software engineering vs. Product Management in tech.

  3. Product management FTW. This is what I do, and it will satisfy many of your project management likes (will also put your scrum cert to great use) and expose you to a lot of the interesting technical work that devs do, without forcing you to take on the insane hours often asked of devs. I rarely work more than 40 hours a week, while some of the devs I work with log multiple 12-hour days when things get hairy. They get paid more than I do, but I think that’s a fair tradeoff considering I am still very well-compensated.

    1. Glad to hear from another product manager! As a dev, I work pretty closely with our product manager and she seems a lot closer to all of the technical decisions than our project manager. It’s great you found a role with interesting tech work as well as reasonable hours!

  4. I think she should make the switch! Especially if she has the financial security to do so. Despite being just a few short years from FI there is no reason to stop stretching career-wise. I work in Healthcare. I went back to school to get a Masters so I could make a career switch in case a mid life crisis hit later on. The crisis hasn’t hit yet but it is good to have options.

  5. Project or product manage sounds like a great career pivot. Like you said, it really depends on your interest and skills set. Agile is all the rage these days and a PMP certification isn’t too difficult to get, so I feel that the barriers to entry are much lower than the developer route. Developers tend to be more specialized and you almost have to be wired to do that kind of work. Some people pick it up really fast, others not so much. Great Q&A!

  6. I don’t think she’ll earn $127,000 without experience, but within a few years she could make close to that much. It would depending on how much effort she is willing to put in. I would suggest working for a large organization with many departments. It can be very helpful to network with people from within rather than attempting to make the jump externally. If her current company has an IT department I would start there. She doesn’t have to say she is looking to make a jump right away. She can simply ask what types of technologies they work with, what she should know, etc. Keep close contacts and converse often. Find out how often people actually code, versus just sit in meetings, etc. Then, one day, with proper training she can make the switch.

    1. Good point, making the moves internally to pick up projects to gain the skills is probably easier than jumping. Networking and shadowing is important too!

  7. Focus on your personality and motivations. Do you like a job sitting a desk, solving problems, and seeing few people? If that is you, you might like the developer job. If you like meetings, working with people and being visible a higher level, manager is for you.

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