Pivoting into Tech

Managing Your Current Job for a Successful Transition + Registration is open


April 29, 2022

Job Search Strategy, Pivoting into Tech

(Photo Credit @aaronburden)

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As we continue on this ‘Pivoting into Tech’ series, today’s focus is on how to best position yourself for a successful transition. You should be thinking about how you can leverage your current role for the next one - and how to not burn bridges behind you.

  1. Plan to Leave with Grace 

    • Consider how you’d like to handle your current job and what kind of departure you’d like to architect. We all love to hear the stories where someone left a company in a blaze of glory, spilling secrets & bad-mouthing management the way you secretly wish you could. But in reality, doing that that will hinder your progress forward in the new role if anyone hears about it (which they will).  

    • Instead, try to think of someone you admire for how they planned their departure from their role. How did they approach keeping up their work product? Their work relationships? The timing of their announcement? It’s better to emulate someone you admire for their ability to design a good departure that shows it can be done. You’ll leave with no regrets. 

  2. Be Aware of Promo/Bonus Cycles 

    • Not everyone has the patience to think about this but it’s worth the effort in the long-run. I had a colleague who was so excited about moving to a new startup that she almost left 2 weeks before our yearly bonuses came out. I convinced her that two weeks in the grand scheme of things wasn’t worth forgoing a healthy financial bonus that she had earned through her hard work. 

    • Are you close to getting a yearly bonus? Aim to make your transition after that date and use it as motivation. You can still be making moves & applying to other roles - just don’t tell anyone yet. 

    • Are you going to be up for promotion soon? I’d advise you to focus on your current role, get the promotion, and then start to make your pivot. You’ll be able to command a better salary and/or title in a new company by leveraging your recent promotion. 

  3. Move your current job into ‘Maintenance Mode’

    • Maybe you’re not interested in bonuses or promotions - you just want to get out asap. Or you’ve already gotten one or both - and your departure is now imminent. 

    • Think about how to move your current job into ‘maintenance mode’ so there are no complaints about your work, but it frees up your brain to learn new things about tech. This will also give you extra time in your week to be sending out applications and building new relationships to help you make the move. 

    • Some clients feel guilty about this tactic but that’s why I highlight the part about no complaints about your work. If you’re a high achiever, it’s hard to just do your job adequately (vs to the absolute best of your ability!) But if you’re not pursuing a promotion, I give you permission to just be average for the next few weeks. You need that energy redirected to your future move. 

  4. Keep your connections with colleagues

    • While I don’t advocate telling anyone that you are leaving until you’ve secured your new role, that doesn’t mean you can’t be intentional about solidifying your relationships with work colleagues that you value. 

    • Take a minute to identify the colleagues who you would like to maintain relationships with once you’re at your new company. What’s the best way to stay in touch with them? Check out this post for a great personal CRM tool to use!

    • Think about whether you want to send individual goodbye emails to these folks or schedule 1:1 coffee chats when you’re ready to leave to highlight your appreciation for being great colleagues. 

  5. Start building a transition guide

    • For some people, starting a transition doc can help make all of this seem more real. You don’t have to spend a ton of time on this now, but jotting down a few notes will help you start to make your transition a bit smoother for everyone. It can also contribute to your ‘making moves’ mindset. 

    • Start a document where you list out your main project(s). Make sure to highlight dates, collaborators, goals, budgets, and status. You can also keep collecting projects and documents you’re working on in one folder. 

    • Note: this can also be useful if you are going up for a promotion as it helps you see the project(s) where you provide essential contributions because you probably wrote those down first. 

I remember clearly that for two of my job departures, I was commended by my managers for being intentional about how I planned my exit & handed off my work so the organization could keep moving forward. 

You should aim to do the same thing as your network is a source of great value in your career - and you want others to remember you as someone who demonstrates care alongside your ambition. 


Find Extra Time and Space to Focus on Your Career Pivot

(Photo Credit @aaronburden)


Interested in joining the Digital Orchards Fellowship to help jumpstart your tech career pivot along with a small cohort of ambitious individuals?

Join the waitlist here: Digital Orchards Fellowship


Yesterday, we discussed how to take stock of where you are in your career & then how to start envisioning your future. You can view that post here: Take Stock + Envision your Future

For many clients, that’s the fun part: looking towards a bright & successful future. And many job pivoters stay in that phase - and don’t progress forward to make that vision a reality. 

Why? There are a host of reasons that can give someone pause when making a career pivot. It’s not the right time to make a move; you realize it’s not the right industry for you; a family situation delays your move, or an unexpected promotion comes your way and improves your current job situation. All of these are among the many valid reasons to stay where you are. 

Today, I want to explore one common challenge to moving forward that is often overlooked but easily addressed: you, the job seeker, haven’t prepared the groundwork to give yourself the time and space to make this change.

  1. The Reality: Job searching takes time 

    • It happens all the time. A potential client says I’m ready to get a job in tech - can you fix my resume? The assumption is that all you need to do is change some words on a paper & that’s enough. Actually, it takes thoughtful review of your current situation & skills to map out a good plan for making a career change. 

    • You will need to open up extra time & space in your life to make this pivot. How are you going to do that?

  2. Map out the tradeoffs you are willing to make

    • Sit down and estimate how much time you can realistically devote each week to making this career change happen.

    • Then try to identify how much time it will take to make the pivot. You can guesstimate that it’ll take one month for every year you’ve worked - but this depends on how big a pivot you’re making, what your transferable skills are, and the networks you can leverage (we’ll cover these a bit more over the next few days). It’s good to have a realistic set of expectations. 

    • Then write up a list of tradeoffs you’re willing to make with yourself, your spouse/partner/family, volunteer commitments, etc.

      1. Maybe this means skipping the Friday night bar scene for a few months? Maybe this means getting takeout for the family every Sunday night so you can spend your evening on your career change? You might also try to postpone a trip that will be right in the middle of when you expect to start interviewing. Or it might mean you need to step back from a volunteer commitment for the next quarter or two. 

      2. Try not to view this as a punishment. This is a strategic choice you’re making to give yourself the necessary time to make this pivot successfully.

  3. Have the conversations you need to have

    • Once you’ve identified what you need to succeed, you need to ensure that key members of your support network are aware of the choices you’re pursuing. 

    • Tell the Fri night crowd not to tempt you for a few weeks - but that you’ll celebrate with them once you get the new gig. Talk to your partner/family and ensure they are on-board with this potential change. Seek out advice if you’re not sure whether you’ve estimated your timing correctly. 

    • All of these conversations help you to gather the support you’ll need to slog through when you get frustrated. And admitting to these trusted folks that you’re looking to make a change makes it easier to start having the future networking conversations too.

  4. Put it on the calendar

    • For me, nothing happens if it doesn’t appear on my calendar. Partly because I need the reminders, but partly because I’ve told myself that I’m dedicating a specific amount of time on a specific day and time to work on a project. 

    • Add recurring appointments to your calendar to remind yourself to work on items related to this career pivot into tech. This is your commitment to yourself that you will make this happen. 

You might be thinking these items are obvious, but humans tend to resist change, even when you do actually want the change to happen. These steps might only take 20-30 minutes but it’s surprising how important they are for long-term career change success. 


Pivoting into a new career can be hard, depending on how BIG the move that you’re making is and how much support you have in making the move.

If you’d like some help with charting out your pivot into tech and you’d like to work with a small cohort of peers making this shift, please consider joining the Digital Orchards Fellowship waitlist: digitalorchards.com/fellowship

Take Stock + Envision your Future

(Photo Credit @lndtxphoto)


Interested in joining the Digital Orchards Fellowship to help jumpstart your tech career pivot along with a small cohort of ambitious individuals?

Join the waitlist here: Digital Orchards Fellowship


Last week, I posted a blog discussing the Top 5 Things You should do to Now to Pivot Into the Tech Industry. It’s been a pretty popular post, so I thought I’d expand upon each of these topics and offer some additional advice. 


  1. Define it: Why are you pivoting?

    • There’s a reason (maybe many reasons) that you’re considering this switch, and you should be clear on what these are. 

    • It helps you identify your motivations for the move, how to avoid similar pitfalls in your new job/career, and gives you the confidence to explain the decision to others too. 

    • It’s also really important to have this solidified so you don’t have regrets later on. We all spend time looking back at choices we’ve made - it’s natural to revisit decisions. The hope is that you review the decision and know that you’d make it again, even if it was hard or went in a direction you weren’t expecting. Building your trust in your decision-making muscles will help you in so many other parts of your life and career. 

    • Unsure? Check out the top 2 questions to ask yourself about whether to stay or go by visiting my post on job-hopping successfully

  2. Write it down & consider these questions

    • Start by writing down where you see yourself in your current career, and where you envision yourself after a successful career transition into tech. 

    • Looking back: Why are you leaving your current role/company? Did it get boring or frustrating? Lack of growth opportunities? Company culture mismatch? Distrust in management? Burnout due to overwork & no one above you seems to care? Need to increase your salary? Try to name the reason(s) and be specific - don’t just leave because you have a vague sense of meh. 

    • Looking forward: Why does tech excite you? What part(s) of the industry make you curious to learn more? What impact do you hope to have in tech? What kind of role will you be in after this pivot? What kind of company did you end up at? Close your eyes - what does it feel like to be in that new role? Sitting at your new desk, meeting new colleagues, tackling new projects? 

    • It’s ok to dream here! This exercise will help you to define why you’re making this move, which will help keep you motivated along the journey. 

  3. Get creative to stay inspired with your pivot

    • Now that you’ve put words to the page that help you see what you want, we need to keep you motivated to actually take the next step. 

    • Easy: create a Pivot Post-It for your desk at home. You could also have one at your desk in the office with nothing but a date on it. (No one needs to know it’s your target departure date but you!)

    • Medium: Add a daily or weekly invite to your calendar. Take a minute to close your eyes, and visualize yourself in your new role. Breathe it in. Live it! 

    • Worth your time: Create a career pivot vision board. I know, I know - I used to think these were kind of silly. But there is plenty of research now on the power of visualization in achieving your goals. You could have a paper one or a digital one, something very simple or with tons of images. The important thing is that (a) you spend the time creating something that will inspire and motivate you, and (b) you look at it regularly & often. 

This is the part of your tech career pivot that should bring you energy, which will help sustain you through the next parts of the journey. 


Pivoting into a new career can be hard, depending on how far the move that you’re making is and how much support you have in making the move.

If you’d like some help with charting out your pivot into tech and you’d like to work with a small cohort of peers making this shift, please consider joining the Digital Orchards Fellowship waitlist: digitalorchards.com/fellowship