Every couple of years I find myself at a career inflection point: that fork-in-the-road feeling of not knowing which path to take next.
The older I get, the less these periods of self-doubt and spinning my wheels completely unravel me, because I’m able to see them for what they are: an opportunity to push back on inertia, evaluate my options, and move forward mindfully.
Follow Ladders on Flipboard!
The best way I’ve found support in moving past these pivot points is through powerful conversation with people I admire. Whether it’s meeting with mentors and advisors or folks I’ve met more recently whose careers I admire, the way I tap into my network and ask for help is the same. It’s all about respecting people’s time and their willingness to share it with you.
After the publication of the Bossed Up Book, I’ve been feeling a bit aloof myself. It’s completely expected after completing a massive goal that I’ve been striving towards for years, and to navigate whatever’s next for me and Bossed Up, I’ve been reaching out to a whole bunch of mentors lately to discuss where I might go from here.
Here’s how I reach out to my network and ask for help:
1. Ask for time
When I reach out for support, I start with a brief email asking my mentor for their most precious resource – some time on their calendar. I never ask the big burly questions I’m wrestling with in the body of the email itself, but instead give them a sense as to why I value their perspective and would love time to connect.
Here’s a recent email I sent to a former professor of mine (whose name I’ve changed):
Subj: Hey David! Coffee?
Hey David –
I hope this email finds you well.
I’m wondering if you might have time in the next few weeks to grab a virtual coffee via video chat. I’d love to catch up properly, and I’d especially love your insights as I come up on nearly 7 years of pursuing Bossed Up.
I’m starting to feel like I’ve hit something of a growth ceiling and would love your thoughts on how I can ensure I’m continuing to set myself up for long-term growth and maximum impact.
I’m just now beginning to think about what’s next for me and Bossed Up and would so appreciate the perspective of someone like you who’s been so instrumental at various points in my career thus far – and whose own career I admire so much!
If you’re down to share a half hour or so of your time, let me know when works best for you!
My best, Emilie
Keep it short, be specific about how much time you’re asking for, and allude to what you’re looking to discuss.
2. Do your homework
In preparing for these conversations, I always take a few minutes to review the online profiles of the folks I’m about to speak with. David recently published another book and spoke on MSNBC, so you can bet I wanted to read up on all his latest and greatest happenings, both personally and professionally.
This helps me connect personally with the appropriate congratulations at the top of our call, of course, and it also helps inform the questions I might prepare to ask. For instance, had I not seen his MSNBC appearance, I wouldn’t have known to ask how he got invited on the network. In the age of social media algorithms, it’s not always easy to passively keep up to date with your friends and mentors, so do your due diligence before your call so you can show you’re keeping up with what’s happening in their life and career, too.
3. Be honest about your challenges
Asking for help is a vulnerable act, which makes it uncomfortable for many of us. But keep in mind: acknowledging that you’re dissatisfied or frustrated doesn’t detract from your achievements thus far. I’m incredibly proud of the work I do here at Bossed Up, but that doesn’t mean I can’t strive for more and maintain ambitions beyond what I’ve already done.
So when reaching out for help, it’s important to be as clear as possible about what’s got you down. Don’t get caught in the perfectionistic trap of saying everything’s “fine” or downplaying your challenges. Articulate them, so the person on the other end of the line can help.
If you’re having trouble putting your finger on exactly what’s got you feeling bummed, try tapping into envy instead. Who do you have a career crush on? Who do you want to be more like? What about them do you admire? Sharing those details can help the person who’s trying to help you get a better understanding of where you’re at and where you’d like to go, which can spur their suggestions and ideas for what to do next.
4. Listen actively
Once you’ve articulated your challenges, resist the temptation to manage the conversation too much from there. Let your mentor or friend spitball some ideas and listen carefully to truly understand what they’re trying to share with you. Ask follow-up questions like, “What do you mean by that?” and “Can you tell me more?” to get them to expand on their advice and share more of how they’ve learned from their own experiences.
It’s ok for these conversations to be meandering. It’s not about landing on a solution right away, it’s about exploring options and following your curiosity. Don’t feel the need to land on a perfect finish line, consider this a start to a broader exploratory conversation, one that can continue via email and future meetups as well.
5. Follow up
After you meet up, make sure to send a thank-you note or gift to show your appreciation and keep in touch as you make progress on your career journey. Send an occasional email update or follow-up question to keep the ideas flowing and as always, look out for opportunities for mutual support.
Be specific about how you’re acting on what your contact shared with you. How have you taken their advice to heart? How are you moving forward? Or still feeling stuck? Loop back with them either way, just be considerate about not constantly asking for one person’s time. When navigating a career inflection point, hearing from lots of different perspectives you respect can help you move forward.