You Know It’s Time for a Career Change. Now What?

Make your career transition less scary and more enjoyable with these five best practices

Jen Dyck-Sprout
10 min readAug 10, 2020

At the start of this pandemic, I noticed most people fell into two camps — they either suddenly found themselves with extra time on their hands, or they were busier than ever. I fell into the former camp, and I felt compelled to help those in the latter. But with NYC in full lockdown, I couldn’t help with child care, or dog walking, so I put a message up on Instagram and LinkedIn essentially saying I was happy to help anyone who wanted to talk about their business, who could benefit from feedback on any of their projects, or who could use help with their resume/job search/interviews.

There was a trend — it turns out that most of the people who reached out to me were thinking about a career transition. I am by no means an expert in this space, but having recently gone through a career transition myself, and having tested twelve different career paths in the last year, I’ve come up with five strategies that can help anyone make their career transition less painful and more successful.

If you are considering leaving your job, or are currently trying to find a new career path, I hope this advice can be helpful to you too.

Five Steps to Transition to a Career you Love

1. Create your own Board of Advisors.

As soon as I quit my job, I tapped a few friends in my network to become more regular thought partners. It helped greatly to lean on people who were doing interesting things already, and who were willing to hold me accountable. For example, one friend had her own podcast, one did participatory art, one invited me to her Mastermind, and another two invited me to join their diverse network for women that was founded to tackle the racial wealth gap.

These friends inspired me to take action, checked in on my progress and offered feedback, they helped me feel more comfortable with taking risks, and they connected me to other amazing people. Their wide range of backgrounds and professional experiences really helped me to broaden my perspective, which improved the quality of my projects.

Building my own Board of Advisors helped me accomplish way more than I thought possible in a short amount of time

If you’re thinking of a transition: Reach out to people in your existing network who inspire you and could help with accountability or brainstorming. Ideally, meet with all of these people on a regular basis as you transition.

2. Network with intent.

With each career path I explored, whether it was documentary filmmaking, building an online course, or doing community management, I quickly learned that I couldn’t do it alone. People often network with the goal of just connecting with people who are already successful in their role, but I found that befriending people who were also new to the given career gave me confidence and courage. Connecting with people who had more experience, was still important, as it helped me move up the learning curve more quickly.

To do this, I reached out to people on LinkedIn, attended panel discussions and introduced myself to people sitting next to me, signed up for beginner classes, joined industry list-serves, and met people at networking happy hours. It turns out there was no shortage of people who were hoping/trying to transition into the same thing at the same time as I was. There was also always someone who had already made a similar transition and was willing to help me. I am convinced this is true no matter what career path you are thinking of trying.

If you think networking isn’t for you, trust me, it did not came easy to me either. I told myself that people wanted these networking opportunities too, or they wouldn’t be here (even if ‘here’ is on LinkedIn), and I was doing them a favour by making the first move. Like with exercise, I also tried to focus on how I would feel after, instead of letting inertia keep me in my comfort zone. Finally, I looked for networking opportunities that were more my speed — for example, I prefer 1:1 conversations that are facilitated through LunchClub (which I highly recommend), than free for all networking happy hours. I also prefer to meet someone through a friend than to send cold outreach on LinkedIn. One of the best ways to meet new people I found was to arrive a bit early to panels, book launches etc, and sit next to someone who looked friendly to strike up a conversation.

Networking not only led me to paid contracts, great feedback, and new friends, it also helped me gain valuable insight before making any big commitments, and also made subsequent networking that much more effortless as one new connection tends to lead to another.

Meeting new people with similar interests gave me a foot in the door and helped me feel less alone.

If you’re thinking of a transition: Network with intent in any new industry or function that interests you until you find at least one person who is also a beginner and at least one person who could play more of a mentor role. Keep looking for new connections until you find ones you like and who can be true thought partners on your journey. I guarantee you are not alone.

3. Take note of everything you learned — it will come in handy!

I left my job thinking I would leave the ed-tech industry entirely. But as soon as I left, several ed-tech companies tried to hire me to do virtually the same thing I had done before. I realized the easiest way for me to get paid was to consult part-time in the domains where I already had the most experience. This could pay my bills while I explored other career opportunities.

So I started to write down everything I had learned in my last job that could help other ed-tech start-ups. As I did this, I realized there were actually a lot of transferable skills and experiences that I had gained. For example, my expertise at building teams helped me recruit talent with complimentary skills to help with my documentary, and my experience working with teachers helped me design a more effective online course.

I have even been able to turn some of these lessons into monetized content through online courses, blog posts, and speaking engagements.

Capturing the knowledge and skills I had gained in my last job enabled me start a “side-hustle” and boosted my confidence that I could transition to a new career

If you’re thinking of a transition: Write down everything you can think of that you’ve learned in your current or past jobs. From specific information about what works in a marketing campaign or meeting agenda, to lessons you’ve learned in hiring or working cross-functionally. It won’t come close to what you’ve actually learned, but you’ll start to see how valuable you could be to a new employer, and the many different ways your experience could translate to other fields and functions. It’s an investment that you may even be able to monetize down the line!

4. Focus on the lessons and joy in the journey, not the destination.

When I started making my first documentary, I couldn’t wait to get out of bed and get to work. I had no idea how the story would unfold, if anyone would be interested in watching, or if I’d ever find distribution for a finished film. Ten months into the project, not one, but two other filmmakers decided they also wanted to make a documentary about my subject, now that they were gaining more influence. Though I understood the subject just wanted more attention to achieve their own goals, I wasn’t too pleased about the sudden turn of events. After months of exclusive access, I started to feel like paparazzi. I hated the feeling. Data.

Four months into writing my first novel, the pandemic hit, and I stopped writing. I wasn’t in the headspace, for obvious reasons, and soon enough, I lost my momentum. Before I knew it, it was summer, and the last thing I wanted to do was continue to sit inside all day staring at a screen. Data.

Ultimately, if you’re on the right path the joy is more in the journey, not reaching the destination. My first documentary didn’t unfold exactly as I would have liked it too, but there were so many lessons I learned along the way about the types of projects I want to work on, and it confirmed that I love the process of making a film.

Similarly, because I was really enjoying writing, taking a step back from finishing the novel didn’t feel like a failure. There was a lot of pleasure and growth in the process. If you don’t love writing, finishing a novel might feel great but you’re going to be miserable for at least a year forcing yourself to write it. And it will really suck if it turns out your novel is a flop!

Rather than giving up on a path or project, I have accepted that sometimes it’s just not the right season or context for a project. Life is long. It’s ok to put something on the shelf to return to at a better time (which I still intend to do with both!), and it’s ok to drop it altogether.

Framing everything as a learning experience allowed me to see any setbacks or challenges as just new pieces of data.

If you’re thinking of a transition: Give yourself permission to experiment and even fail. Ask whether you’re still enjoying the journey or if you’re just chasing a destination. It’s all a learning experience, but ideally the journey is satisfying to you. Remember that sometimes a project or goal has a longer time horizon than you initially anticipated.

5. Don’t worry about getting things perfect at first. Just start.

You could say I’m a perfectionist, but I think everyone has a bit of a perfectionist in them. We all tend to avoid things we aren’t good at. So starting something new is always pretty uncomfortable, if not downright scary. Thanks to the internet, we now have unlimited (often free) resources at our fingertips to help us become experts in virtually anything our heart desires.

After a few weeks of learning about filmmaking, I felt like I had barely made a dent in how much there was to learn. All the filmmakers I admired had years, even decades, of experience, and often formal education. How would I ever catch up? So I kept trying to suck up as much information as I could, which was convenient, because then I didn’t have to actually confront my insecurities. I was so nervous to actually put a camera in front of someone and start shooting, especially out in public. What if the audio wasn’t perfect? (Better learn more about audio!)What if there was music playing? (Better also learn more about legal!) What if my camera wasn’t good enough for the lighting? (Better learn about lenses.) What if the best camera was way out of my budget (of course, they all were)? (Better start learning about grants and funding options.) You get the point.

Soon enough, I realized that I could easily spend months (or longer!) learning from experts about any given topic, or I could just start doing and accept that I won’t be perfect. It became clear doing taught me more, and more quickly, than learning. I just had to accept that it would feel uncomfortable.

It is easy to hide from the real work by continuing to engage in passive learning activities (taking online courses, reading advice, listening to podcasts). But what is the point in going down rabbit holes learning the ins and outs of editing with Premiere Pro if we don’t start applying what we’ve learned? Just start. Beyond being a more valuable learning experience, there are so many benefits to starting before you’re ready:

  • the momentum starts to build
  • it makes networking easier because you have better questions to ask
  • you’ll be seen as a doer, not a just talker — people like to be around someone who follows through
  • you’ll start to build your ‘portfolio’ which will make you more employable
  • you won’t have to wonder how things might have been if you’d just tried
  • you can avoid future regrets
  • you’ll feel more satisfied making tangible progress to your goals
  • you’ll gain valuable data about your strengths and interests
  • you’ll get better at differentiating between insecurities and valid reasons not to do something

One of my favourite sayings is “Modern Art = I Could Have Done That + Yea But You Didn’t.” I’d take someone who tries over someone who talks about trying any day. Just take one step, even if it is the smallest, simplest step you can image.

Modern Art=I Could Do That + Yea, But You Didn’t
Source: Odyssey

Accepting imperfection allowed me to shift from learning to doing

If you’re thinking of a transition: Try to strike a balance between passive learning and active learning. Set a cut off for how long you will be in “learning” mode until you switch to “doing” mode. Taking action is really the only way to get data, and you’ll quickly learn if you enjoy something or have a knack for it.

It’s hard enough to figure out what we want to do with our lives, let alone find the courage to make the changes needed once we know.

It’s no wonder there are so many start-ups popping up to help professionals upskill and navigate this rapidly changing job market. Even with my education, my confidence, my network, my determination, and my resources, I can’t say I’ve successfully broken into a new labour market. But I’m leaning on my Board of Advisors, continuing to build my network, focusing on the lessons I’m learning, and leveraging what I already know to gain traction.

I know I won’t be successful in a new career overnight, but by following these lessons, I can see I’m slowly making progress, and most importantly, I know I’m on the right path because I’m enjoying the journey.

Please feel free to reach out if I can be of any help to you in a career transition, I’m happy to help where I can. If you don’t know where to even start, I suggest going through the seven steps I’ve outlined here to help you find a career you love.

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Jen Dyck-Sprout

I help mission driven startups and leaders scale their impact. I write about the future of learning & work here: