4 steps to a successful career transitionFeatured

JennyLuu's profile thumbnail
Thank you for the step by step guidance! It helps make the transition feel less daunting; I'm currently in step 2, and self reflection. Looks like I have quite the journey to go but this is very helpful so I don't get carried away to just leave and jump into whatever is next. Bookmarking this!
ToryWobber's profile thumbnail
So glad this was helpful to provide structure, @JennyLuu. I'm confident that by taking the time to move through each of these steps, you'll land somewhere that works well for you!
What are some other options for Step2? What are your thoughts about asking a team you are interested for a side project? Would the optics be bad?
ToryWobber's profile thumbnail
Great question! To me, that sounds like a viable way to explore alternative options - though you are more of an expert than I am on the particular culture of your company. How do you think the optics would look?One idea: if you have a trusting relationship with your manager, you could communicate your intentions with the side project to be sure they are informed and bought in on you exploring new skills while remaining committed to your current role. What do you think?
SueCopeland's profile thumbnail
Thank you @ToryWobber. I am on step 3..... it's been a long, sometimes difficult process but I am confident that it will be all be worth it!
ToryWobber's profile thumbnail
I am confident in this as well, @SueCopeland! Keep finding ways to take care of yourself as you go - the journey itself can be draining, even if the end goal will yield more fulfillment for you.
ambika's profile thumbnail
Brilliant and tactical advice--really strikes an emotional chord. Love what you're doing and would love to connect!
ToryWobber's profile thumbnail
Amazing, thanks so much @ambika! If you'd like to set up time to chat, feel free to snag a window on my calendar: https://calendly.com/tory-coaching
SorumPanchal's profile thumbnail
What a timely and detailed post. I've been trying to organize my thoughts around my own career plans, and your notes here include so many small but vital things that deserve consideration. Cheers!
ToryWobber's profile thumbnail
Glad this is coming at the right time for you, @SorumPanchal! My hope is that this helps provide an over-arching structure without neglecting any of those details. Best of luck as you make your next move.
Great post! Thank you!! I especially love the point about not seeing interviews as tests. I really wish tech and engineering role interviewers got the same memo. The good interviewers see a technical interview as a 2-way problem solving exercise but I’ve found that many technical interviewers approach it with the ‘I’m testing you’ mentality. In some cases, they are praised by their peers or seniors for being the ‘hardest interviewer’. As an interviewee, how can we combat this (aside from deciding to avoid working with that person or team)?
ToryWobber's profile thumbnail
Great callout @rutha128! My position on this may be somewhat controversial, but I lean towards what you suggest at the end - if a person is deciding to subject an interviewee to a deliberate "stress test," what does that suggest about how they will treat an employee on the job? In my first role, my hiring manager gave me a "stress test" interview and it turned out to translate to a culture on the team where there was a high tolerance for incivility, with expectation to "grow a thicker skin." I took the role because at the time I wanted *any* job, but in retrospect I can see that the interview provided me with a concrete signal of what the culture would be like. In my later interviews, I implemented a "no jerk" threshold as part of my assessment, with the logic that if someone is a jerk even in a best behavior situation like an interview, they may be even worse on the job. An alternative approach, if you're feeling courageous, would be to label what's happening during the interview. This could be something along the lines of "Hey, this line of questions feels like it's putting me in test mentality but I'd like to approach this topic collaboratively, as though we're working on this problem together as colleagues. How does that sound?" I don't know that I would have had the presence of mind to do this myself, but it could be a really interesting way to cut that tension by calling it for what it is. What do you think?
sarapopo's profile thumbnail
Great tips @ToryWobber! Thank you. I love the advice about using informational interviews to perfect the career journey elevator pitch! I've got work to do!
ToryWobber's profile thumbnail
Awesome, @sarapopo! I am such a huge fan of informational interviews as serving a wealth of purposes, so I'm glad that you are excited for what you can gain from the process. I know the work you're putting in will translate to amazing outputs for you!
EvelynC's profile thumbnail
This is great! A book I recently finished and highly recommended as part of the soul searching/wayfinding is called Designing Your Life. The book has some very interesting exercise.And Tory, you’re totally spot on jumping in the application process. I find myself doing that sometimes. So my question is: when do you know you’re ready to apply?
ToryWobber's profile thumbnail
Great question, @EvelynC! My 2c: I'd say you're ready to apply once you have a decision on 1-2 target roles along with an idea of the size of company and industry that you're interested in. My rationale here is that if you're applying across a broad set of opportunities without a concrete decision on what you're excited about, your resume will have a lower chance of being a match. You may also have to endure more rejections, which can harm your self-confidence. On the other hand, if you're targeting 1-2 roles at a consistent type of company, it's easier to tailor your resume and prepare yourself for the types of interviews you'll encounter. In terms of timeline, I'd recommend that you carve out a few weeks - 1 month where your primary goal is to explore. If you find yourself feeling a need to apply faster, check in with where that sense of urgency is coming from. If you find your exploration phase spans 3+ months without any applications, then I'd recommend checking in with your decision-making process. How does that sound to you?
MargothPicado's profile thumbnail
@ToryWobber I was forbidden to explore things when I was young. I am 31 years old now, and I am changing careers. I feel like I want to explore all at once and I also feel like I want to work a lot on what I want to achieve. It's very confusing... Sometimes I don't know if I am doing things faster than I should or if my process is in the right path. I didn't even know if changing careers was allowed at 31 LOL. Thank you a lot for sharing this post.
ToryWobber's profile thumbnail
Glad you found the post helpful, @MargothPicado! It is ABSOLUTELY OK to switch careers at 31. It'd be OK to switch careers at 41 or 51, in my book - but maybe I'm unconventional in this respect ;) I'm certain that you are moving at just the pace you need to. Feel free to DM me if you'd like to have a sounding board for any of your specific ideas. Take care!
elizabethanderson's profile thumbnail
Tory- thank you so much for sharing this detailed outline! I am curious how you suggest requesting informational interviews? The primary networking platform I am on is LinkedIn, and I am assuming this is the best platform to request them on. If LinkedIn is the preferred platform to request informational interviews, should I connect with people before sending a message or use the premium InMail feature to direct message? Is it appropriate to be straightforward and directly request an informational interview or should I go about it in a more nuanced way? Would love to hear your thoughts on this!
ToryWobber's profile thumbnail
Great questions, @elizabethanderson! Any platform works. I often like to be upfront about requesting the informational interview, framed within genuine flattery. Something along the lines of - "Your job looks fascinating. Could I ask for 30 minutes of your time to hear more about your role?" One thought I'll put out there: "cold" messaging on LinkedIn may have a low success rate if folks don't know you and are skeptical of new connections coming their way. I typically recommend starting your info interviews with your first-degree network and then asking them for introductions to folks in areas that you're exploring. I've usually seen more success with "warm" introductions where you have a mutual acquaintance than "cold" outreach, though the success rate of the latter isn't zero. In case it's helpful, I've written up a free guide to informational interviewing. You can check it out here:https://mailchi.mp/5954e7b2c019/79v0332tlfHappy searching!
elizabethanderson's profile thumbnail
Thank you so much for your input Tory - this is all incredibly helpful info and I am excited to start reaching out to others. Thanks again!
ToryWobber's profile thumbnail
Hi folks! If anyone is curious in getting more detail on these 4 steps or asking questions that may have come up for you along the way, I've got a webinar coming up hosted by Chapter 2 Club on June 22nd:https://www.chapter2club.com/workshop/the-4-stages-of-a-career-transition/Hope to see some of you there 🙌
rachelserwetz's profile thumbnail
Thank you for sharing such insightful tips! For those in a similar position looking to make a career transition : Hi! I'm Rachel Serwetz, an ICF-certified career coach. My background is at Goldman Sachs & Bridgewater Associates, before moving into the career space to systematize my novel career exploration and job search methods and tools.My mission in life is to ensure people feel supported in making these critical, impactful career decisions. These decisions can feel stressful and tough, but with the right support (which you deserve), you can feel relieved, excited and confident in your next steps. I have been coaching hundreds of professionals for over 8 years and have developed unique processes and frameworks so that you can confidently clarify your ideal career direction and efficiently job search to land a role you feel fulfilled by. Happy to chat directly and see how I can help! calendly.com/woken/demo Best,Racheliamwoken.com