Make the Most of Your Career Transition with Introspection, Bravery, and Community-Support

Making a plan when you’re switching industries can be difficult. Here’s how to make a career transition with introspection, bravery, and community-support.

 min read
April 14, 2022
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Note: If you’re an early-stage founder anywhere from pre-idea through pre-seed, consider applying to On Deck Founders

Note: This article is adapted from a live discussion for the On Deck community featuring On Deck alums Ming Lu and Vik Duggal. If you’re an early-stage founder, angel investor, or exec interested in joining our community, consider applying to one of our programs - you’ll be in great company.

Note: If you’re an early-stage founder anywhere from pre-idea through pre-seed, consider applying to On Deck Founders.

Note: This article is adapted from a live discussion for the On Deck community featuring Josefin Graebe. If you’re an early-stage founder, scaling founder, or senior exec interested in joining our community, consider applying to one of our programs.

This article is the first in our annual series Year in Preview.  In the 4 years since we launched the On Deck Founders program, we’ve seen +1000 companies get started and raise over $2B in funding.

There are four types of career transitions that people make: being fired or laid off, escaping a dead-end job, receiving an unexpected opportunity, and deciding to take a leap of faith. Change is scary, but career transitions don’t have to be; they are an opportunity to grow personally and professionally, and can bring you closer to your ideal position. 

To prepare for an upcoming career pivot, make sure to understand what you want, take advantage of your network, and find ways to be brave in face of the changes ahead of you. 

First, Take Some Time to Introspect

When thinking about a career transition, it’s integral to have a specific goal in mind. Ask yourself the following questions and be honest with your answers:

  • Why are you transitioning? (or, if you were laid off: Why were you let go?)
  • What do you want to do next? 
  • When do you want to do it? 

Be realistic about your career priorities and your tolerance for risk as well. For example, the riskiest venture is the one that you start yourself, but this may also have the highest opportunity for reward. If your priority in your career is to achieve more stability, you would want to opt for a mid-to-late stage startup where the road ahead is a bit more clear and the pay is often higher. For those early in their career who value their growth above all else, early-stage startups can be ideal fast-paced learning environments. 

That being said, not all startups are created equally, and there is variance in risk within each stage. During your job search, evaluate your risk appetite and career priorities alongside a company’s fundamentals like its investors, business plan, product, founder persona, culture, and more in order to ensure it is a strong fit. 

Matrix of startup stage and risk, growth, pay, and equity

Consider which of your skills might carry over well to another endeavor, and which new skills you’ll have to learn to make a successful transition. For example, if you’re switching jobs from a designer to a manager, your foundational design skills, soft skills like empathy and listening, and system design expertise will carry over, but you may have to do some work to develop your capacity for delegation, effective communication, and coaching and employee development. 

To build these skills ahead of a transition, consider opportunities like On Deck or one of the many online learning platforms at your fingertips. Depending on the experience level you’re starting off with, be realistic with the amount of time you’ll need to reach the proficiency that your next job requires, and plan your job search accordingly. 

For example, if you’re learning to code from zero, you want to sign up for a bootcamp quickly and wait until you’ve completed it before you start scheduling interviews. If your communication skills are strong and you merely want to level them up for your next role, consider doing a class in tandem with your search and sharing your progress with potential employers. Chances are, they'll be impressed by your commitment to improvement, and by your dedication to what you want to do next. 

On Deck Founders Fellow Rehan Choudry knew what he wanted: to pivot to a job where he was creating change in the mental health space. COVID-19 had begun to spread, and Choudry found himself deeply affected by people’s inability to attend their loved ones’ funerals. 

“I started going down a rabbit hole and trying to figure out how big the issue is and how much good we could do with it,” Rehan said. 

His introspection and passion led him to make a career transition and found Chptr, a platform for crowdsourcing the life stories of loved ones who have passed, alongside On Deck Fellow Perfecto Sanchez.

Another On Deck Fellow, Anne Ferracane, had spent over twelve years in tech and was ready to dive into entrepreneurship — but she didn’t know where to start. 

“When I was coming into On Deck, I was trying to figure out: Do I want to be a founder? Do I want to be an investor? Basically, what do I want to do next?”

On Deck allowed her to answer these questions and clarify her goals for her career pivot. Through this process, she was eventually able to found Patch Ventures, a company that invests in and incubates technology products that provide economic opportunity and increase access to information. 

As you approach a transition, take time to be deliberate about answering key questions and making sure you know what you want to pursue in the next stage of your career. However, regardless of how well you’re able to define your goals, there’s no right answer in deciding what you want to do next, and there are no guaranteed outcomes. All pivots require an element of bravery as you take the next leap of faith. 

Build Up Your Bravery

Leaving a comfortable position can be scary. 

When Amazon founder Jeff Bezos told his boss that he was thinking of quitting his lucrative hedge fund job, his boss was shocked, but a regret minimization framework allowed Bezos to be brave. He asked himself: When I’m 80 years old, will I regret building something I was passionate about and failing, or not trying at all? The answer, in his mind, was obvious. 

While we’re not all Jeff Bezos, we can all ask ourselves this question at times when our bravery is running low: Will I someday regret not doing this? 

On Deck Fellow Rico Meinl followed his bravery and dropped out of university to start a company called Dresswell that used machine learning to help shoppers identify their clothing size across different brands

He and his co-founder pivoted various times in order to gain product adoption, and soon found themselves far from their original vision. After a little over a year of operation, they made the decision to close the curtains on Dresswell. 

“Leaving this project behind, after having invested so much time, as well as emotional and financial resources was not an easy call but there were tons of learnings and experiences that I took with me,” Rico said. 

He soon took a job at an established retailer, but began to miss the pace and excitement of working at a startup. He wanted to return to the startup scene not as a founder this time but as an early employee. Rico joined On Deck First 50 and found Talus through On Deck’s contract-to-hire platform, Lean Hire. His interests and skills aligned with their vision, and today Rico is their Lead Machine Learning Engineer 

Part of being brave is also facing the misconceptions and judgments you might hold about career transitions. We’ve all heard and perhaps internalized some quasi-helpful advice like “You have to stay in a job for at least two years” or “Don’t leave a job without another one lined up.” 

These may be true in some cases. For example, it does look bad to employers if you have multiple one-year stints at different companies in a row, and it’s not advisable to quit your job if you don’t have the financial security to maintain your standard of living while you are searching for a new one. 

But while these adages may be true in some cases, the market is always changing, and workforce norms are changing along with it. Case in point: 55% of employers said they hire job-jumpers, and 32% of employers said they expect it. 53% of employers see the benefit of switching jobs, and believe that those who do so bring a wider range of expertise to the table.

When employees are most likely to quit their jobs

That being said, expectations do vary by candidate age and industry. Leaving a job within two years is most acceptable, for example, for recent grads and in industries like information technology. 

Whatever your case may be, staying at a job that makes you truly unhappy is rarely a great decision, and having the bravery to leave when you want to, and explore opportunities that excite you, is integral to navigate career transitions intentionally. 

Reach Out To Your Network

Whether you’re feeling lost in your career or just looking for people to help you navigate your next steps, accessing a network of peers and professionals can provide support, connections, and motivation at a crucial time. 

In fact, while online job boards like Indeed and LinkedIn are still the most popular forum for job searches, other methods are gaining ground. In a 2019 survey, 50% of people reported having found a job through friends, 37% said they found a job through professional networks, and 35% said they found a job through social media. 

Don’t worry if you don’t have these key connections yet; there are dozens of ways to build them. If you’re working from home, follow our guide for networking for tactical tips on traversing the landscape of online networking events, participating in professional Slack communities, and mastering cold outreach. 

Joining an established community like On Deck can also provide access to a network that will help with your career pivot. 

For Daniel Gamboa, having other On Deck fellows to share experiences with made him feel validated in his job search. “He realized that he wasn’t alone... the community helped him see that it’s completely normal for people who work in startups to jump around.”

To aid his job search, Daniel took advantage of the “matchmaking aspects” of On Deck, where Program Directors help connect Fellows to one another and to relevant startups in the extended community. 

Luba Yudasina also benefited highly from the On Deck community. She wanted to start her own company, but she didn’t have anyone in her immediate circle who was working in that sphere. 

“I didn't really have that support network of like-minded people. When On Deck came around, I thought it was the perfect opportunity to surround myself with like-minded people, and hopefully I could find out what the founder’s journey would look like for me, personally,” Luba said. 

Luba Yudasina’s Twitter

Eric Jacobs knew he wanted to switch careers and do something different, but he didn’t know what that next step would be. On Deck First 50 gave him the time, space, and most importantly, the network, to figure that out. “The job search, in general, can be a very lonely experience, but having a community that is going through the same experiences, challenges, uncertainty, and being able to share new ideas to keep the momentum going was probably the most helpful about the program.” 

OD50 gave Katy Culver access to startups, talent demo days, workshops, fireside chats, and career coaching, all of which gave her the tools to be successful in her career pivot. But for Katy, the best thing about On Deck was the community.

“On Deck’s application process filters for givers -- people who look to give to others more than they take. This creates a virtuous cycle of support among community members and the On Deck team.”


Whether you’ve just been let go from your company or you’re approaching your career change voluntarily after months of deliberation, career transitions can be daunting. Any kind of change is difficult, but that doesn’t mean it shouldn’t be exciting as well. To make the most of your career transition, introspect and understand your goals, bank on your bravery, and utilize your community for support and connections.

Note: If you’re an experienced professional looking to gain clarity on your next move, check out Execs On Deck

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