Make the decision, and fully commit.<\/strong> Don\u2019t dilly-dally nor go back and put the call you made into question. Honor the work you put in to get here. Trust your judgment. <\/li>\n<\/ol>\n\n\n\nNow let\u2019s review a few practical examples from my coaching practice and hypothetical scenarios. <\/p>\n\n\n\n
Known Knowns (Facts)<\/h4>\n\n\n\n
If you start here, you understand the problem at hand, its context, the underlying principles at work, and feel confident in the consequences of your decision. You have been through this decision hundreds if not thousands of times. <\/p>\n\n\n\n
What this may look like career-wise is you have a few years of experience in a domain under your belt, are known as a subject matter expert by your peers, and are evaluating how to turn your hard-earned knowledge into new career opportunities. <\/p>\n\n\n\n
Strategies<\/h5>\n\n\n\nLeverage Your Knowledge to Learn New Skills<\/h6>\n\n\n\n
If you have built a solid foundation of knowledge in one skill, you can use it as leverage to shift into newer, adjacent domains. <\/p>\n\n\n\n
One of my clients, let\u2019s call him David, was a reliability engineer at an automotive startup. After a re-org that impacted his role, he looked for new internal opportunities and received offers from two different teams. One offer was from a different reliability team, where he was confident that his responsibilities would remain the same on his current team. <\/p>\n\n\n\n
The other offer was for a newly formed test engineering team, which was riskier but would teach David relevant skills that he was hungry to pick up. David took the latter offer, capitalizing on his existing contributions to the company and converting them into an opportunity to learn about a brand new, adjacent skillset.<\/p>\n\n\n\n
Last time I checked with him, he was feeling happy and fulfilled on his new team.
Start with what you already know and expand outward into lateral areas of knowledge and skills. <\/p>\n\n\n\n
Double Down on an Area of Expertise<\/h6>\n\n\n\n
Sometimes you\u2019re confident that you have the potential to thrive in a skill(s) based on your previous performance and enjoy the work. Then it makes sense to double down and build deeper expertise. <\/p>\n\n\n\n
When I left my 120-person online education startup to join Dropbox\u2019s growth team, I had been learning a product optimization skillset for two years. I knew that I felt happy doing these responsibilities and wanted to build up my seniority by working at a well-resourced company that would invest in my learning in this particular sub-field. After 3.5 years of working at Dropbox, I gained valuable depth and a portfolio of experiences. <\/p>\n\n\n\n
Take what you already know and build on top of it to develop expertise. <\/p>\n\n\n\n
Known Unknowns (Question)<\/h4>\n\n\n\n
Here you haven\u2019t attended this rodeo before but you have an informed opinion on what\u2019ll happen as a consequence. Perhaps you\u2019re trying to break into a new field or industry, gain management experience, or work for a company at a different stage of its lifecycle than your current employer. <\/p>\n\n\n\n
What you want to do next is ask some juicy questions. <\/p>\n\n\n\n
Strategies<\/h5>\n\n\n\nSeek an Insider Perspective<\/h6>\n\n\n\n
Take your questions about a prospective opportunity and ask someone for their advice who has walked this path before. <\/p>\n\n\n\n
If you\u2019re applying to a position at a new company, set up an informational interview or coffee chat with a current or former of that team. By learning from their experience, you\u2019ll often unearth golden nuggets of insight about the team and company that no one else has access to. <\/p>\n\n\n\n
Considering a total career make-over? Great. Reach out to your network\u2014including your 2nd and 3rd degree connections\u2014that work in your desired field. <\/p>\n\n\n\n
Recently my client, let\u2019s call her Rachel, was considering a jump from investor relations in the world of finance to the software industry. With the wide breadth of roles available, she felt confused and intimidated. It wasn\u2019t until she chatted with actual professionals in the industry, including me, that she cut through her mental fog and formed a clearer picture in her head of where she fit. Ultimately she decided to pursue a new role in finance, but knowing the specific roles in software that she was comparing against helped her accelerate the decision-making process. <\/p>\n\n\n\n
Once you have questions, talk to someone more seasoned in doing what you want to do. What\u2019s unknown to you is likely known to others. <\/p>\n\n\n\n
Run an Experiment<\/h6>\n\n\n\n
Another way to answer your question is by putting your career hypotheses to the test. This strategy works especially well if you can do a low-cost experiment to assess whether or not it makes sense to commit more resources behind a decision. <\/p>\n\n\n\n
Let\u2019s pretend that you\u2019re interested in transitioning from software engineering to marketing. Don\u2019t put all your eggs in this new basket until you know you like it and can deliver great work. If you start applying to marketing job postings left and right, firstly you\u2019re going to have a tough time getting through interviews without prior marketing experience. Or worse, you receive the offer and then get stuck doing work you hate. <\/p>\n\n\n\n
Start with a small marketing project instead. Volunteer to help a non-profit with market research and positioning, freelance paid ads for a startup, or ask to help your co-worker with a product launch. Validate that you enjoy the work and can excel at it before you sink in more time, effort, and money. <\/p>\n\n\n\n
Unknown Knowns (Intuition)<\/h4>\n\n\n\n
There may be biases at play in your situation that you\u2019re not currently aware of \u2014 but they\u2019re obvious once they\u2019re apparent to you. You may be in a fast-growing startup with a constantly shifting culture or a corporation that recently introduced new top management. <\/p>\n\n\n\n
How do you promptly surface these biases so they don\u2019t cause you disappointment and frustration in the future?<\/p>\n\n\n\n
Strategies<\/h5>\n\n\n\nAsk Yourself, \u201cWhat Was True About Last Month That\u2019s Not True This Month?\u201d<\/h6>\n\n\n\n
You can be certain that the needs of a rapidly changing business never stay the same. What was celebrated and rewarded last month or quarter could very well be what\u2019s holding back the business this month or quarter. And if you\u2019re caught blind-sided by these shifts in the landscape, you could end up in a world of hurt and resentment. <\/p>\n\n\n\n
A common grievance I noticed amongst my colleagues at Dropbox (and friends at other high-growth startups) was that they had sunk their prime years into building the company, only to watch executives recruit outside talent to come in and become my colleagues\u2019 managers. They felt hoodwinked for all their loyalty and dedicated efforts. <\/p>\n\n\n\n
In startup land, one hears this complaint all the time from hardworking junior employees: \u201cUgh I can\u2019t believe they hired X above me! Look at how hard I work. Why am I always getting passed for promotion into leadership opportunities?\u201d <\/em><\/p>\n\n\n\nOne reason is that the scrappy, \u201cget things done at any cost\u201d mentality that leadership praised them for during the company\u2019s high-flying startup phase wasn\u2019t what the organization needed in the pre-IPO\/public corporation phase. The latter demands new skills such as structured thinking, strategic planning, and ability to manage large swaths of stakeholders. In this new context, scrappiness goes out of fashion. <\/p>\n\n\n\n
Without questioning your own intuition, it\u2019s easy to get wrapped up in your ego-centric view of the business and not notice these broader, underlying shifts. Nothing may have changed about your physical office space, direct team, manager \u2014 or even responsibilities on-paper. But below the surface, everything has changed. <\/p>\n\n\n\n
Take a moment to reflect. Question the biases at play in your own view of the world, adjust your expectations, and learn how to adapt to the new organization. This may mean up-skilling, switching roles, or even leaping to a different employer at your preferred stage of the business lifecycle. <\/p>\n\n\n\n
Unknown Unknowns (Exploration)<\/h4>\n\n\n\n
You\u2019re faced with a lot of uncertainty, which requires a completely different set of tools. Perhaps you\u2019re considering opening a new business, joining an early-stage venture, or taking a sabbatical. <\/p>\n\n\n\n
What I\u2019ve observed is that high-achievers tend to have a perfectionist streak. I know, because I\u2019m one of them. For most of their professional lives, they\u2019ve learned to identify the game being played around them, discover its hidden rules, then architect a path forward to winning. <\/p>\n\n\n\n
The downside of this approach is perfectionists struggle with an unknowing future. Their natural solutions for data-rich problems don\u2019t translate well to data-void possibilities. Trying to apply logic and reasoning to a black hole of uncertainty tends to cause more anxiety and stress than it\u2019s worth. <\/p>\n\n\n\n
Strategies<\/h5>\n\n\n\nLead With Your Values<\/h6>\n\n\n\n
When standing on the ledge and looking down into the unknown, trust your instincts and let your personal values guide your decision-making. They are like a steady compass when you find yourself immersed in darkness. The result is a feeling of quiet self-assurance and being grounded\u2014that no matter what happens, you feel satisfied for having lived your truth. <\/p>\n\n\n\n
When I made my personal decision to take a travel sabbatical, I had forgone a few enticing job offers on the table. In the moment, it felt like throwing caution to the wind. I remember feeling my stomach churning and being short of breath as I committed to pulling the trigger. Yet I\u2019m grateful for listening to my values and loading up on courage. I couldn\u2019t have planned for the amazing people I met \u2014 and the coaching business I had the opportunity to build \u2014 due to serendipity and freedom. <\/p>\n\n\n\n
It\u2019s challenging to do a logical risk calculus of the total unknown. In the absence of illuminating data, use your values as the compass. <\/p>\n\n\n\n
Think of Everything That Can Go Wrong<\/h6>\n\n\n\n
Imagine that the decision goes horribly wrong and then write out all the possible ways this result could have happened. While you won\u2019t be able to prepare for 100% of these scenarios, when the time comes, your conditioned muscles will spring into action more quickly. <\/p>\n\n\n\n
This tool is called a \u201cPre-Mortem<\/a>\u201d and is used by software development teams, hedge funds, and military officials alike. It\u2019s particularly useful in career decision-making, especially when taking a big risk such as investing your life savings into starting a new business. <\/p>\n\n\n\nOne of my peers recently left her high-paid tech job to launch her own venture selling a new productivity journal. She planned her departure strategically \u2014 not rage quitting without a safety net. Before she took the leap, she assessed the ways the venture could fail, tying her timeline for leaving her job to key business milestones. And she further derisked her proposition by launching with a pre-sale instead of a standard e-commerce store to avoid potential cash flow issues. <\/p>\n\n\n\n
It\u2019s certainly more fun to imagine the ways you can achieve your wildest dreams. However, for high-risk decisions, it\u2019s worth doing the upfront work to eliminate the potential for ugly surprises down the road. <\/p>\n\n\n\n
\n\n\n\nAdapting to the ever-changing business world is stressful and challenging. Luckily, we have timeless decision-making frameworks like Knowns and Unknowns, which has been adopted by ancient philosophers to modern-day NASA mission planners. <\/p>\n\n\n\n
Using this quick-and-easy tool, you\u2019ll make faster and better decisions in a wide variety of career transitions. And it\u2019s one that you can refer back to for the rest of your life.
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