I’ll never forget how it feels to be stuck.
Let’s go back in time to my first startup job.
I’m sitting at the counter at Harlow, my favorite healthy breakfast spot here in Portland.
As I wait on my food, I take off my rain suit to let it dry until I have to get back on my bike. I reach down and grab my notebook out of my bag to do what I’ve been doing every day lately: read my morning affirmations.
I read them to myself:
- “I am loved”
- “I am worthy of respect”
- “I am good at what I do”
I read 6-7 of these affirmations every morning to help me prepare for the day of work ahead of me. Things are that bad at work.
After months of being manipulation and gaslighting, I lost all confidence in myself. Every week I had questions running through my head… Is there something wrong with me? Am I dumb? Do I not know what I’m doing? Are my ideas bad? Why does he keep stealing my projects after saying we shouldn’t pursue them? Are we trying to grow the company or am I just here so the founders can pass the less enjoyable work off to me?
I had never before and I have never since needed to start my day with affirmations in order to feel like I can tackle the day ahead. There is nothing wrong with affirmations, but the mere fact that I needed them to keep going should have been a sign: I was stuck.
When I ask each new subscriber to Career Capital about the biggest hurdle in their career, I hear one thing most consistently: I feel stuck!
I’ve been there. If you’re not there right now, I bet you’ve been there before too. And I bet every one of us will experience it again in the future.
Are you stuck?
When you’re stuck, it’s hard to see clearly.
Being stuck can happen for a host of reasons, but it might look like:
- Staying in a job for the money because you’re afraid you won’t have the same earning power in a new role or company
- The company flatlining or shrinking in revenue and/or headcount, leading to a lack of personal growth
- Having to move cities in order to find new opportunities, which is too high a cost for your family
- Reaching the top of your current career ladder unless your boss or one of her colleagues leaves the organization
- Going through the motions because you’ve been doing the job for so long
- Working so many hours that you’re too exhausted to think about whether you might be stuck
- Being in a toxic relationship with your manager or colleagues (this is what I was experiencing in my opening story)
If any of these things resonate, you might be stuck.
It’s worth checking in with yourself every six months by asking a couple of questions:
- Do I have more days when I wake up excited to get to work or dreading the work?
- When is the last time I enjoyed a project so much that I lost track of time at work?
- When is the last time I felt uncomfortable because of a challenge pushing me to grow at work?
- Have I solved any hard and interesting problems lately?
- When did I last receive meaningful feedback? Is there a clear path for growth for me?
- Are my manager and colleagues more likely to tear me down or build me up?
- Why am I doing this job? Am I still in this for the right reasons?
- Is this what I want?
Merely sitting in quiet solitude and writing your answers to these questions will give you clarity on your relationship to your current role and company. Most likely this won’t be a surprise, it will simply solidify something you have been feeling in your heart or gut.
Do you know what you want?
For many people, knowing you’re stuck isn’t the real problem. The real problem is that you don’t know what you want.
I typically see two responses to being stuck without knowing what you want:
- Staying stuck, which is by far most common
- Jumping from job to job chasing more money/prestige/greener grass
Both of these approaches are mistakes. In either case, you’re harming your own career and the organizations you work for. If you don’t know what you want, hopping from job to job very quickly looks like 1) you don’t know what you want or 2) you purely chase jobs for the money.
Job hopping is not inherently bad. When you know what you want, changing roles can be one of the most effective ways to find the role and company. In this case, job hopping helps you take a lot of shots on goal until you find what fits your career vision.
Get clear on what you want. Then act.
The most important step to take to get unstuck is to get clear on what you want. Don’t pout. Don’t start applying to jobs. Get clear. Then act.
There are three basic questions you need to answer in order to get clarity:
- What kind of life do you want?
- What kind of company do you want to work for?
- What kind of job do you want to do?
There is more material here than we can cover in one issue of Career Capital. My workshop, The Most Meaningful Job of Your Career covers this framework in detail.
When thinking about your life, you need to think about your life in a multi-dimensional way. This means considering your spiritual life, relationships, finances, physical wellbeing, mental wellbeing, the travel and adventure that rejuvenates you, and, finally, your career. In this context, your career is one small aspect of your life that gives you leverage to create the life you want for you and your family.
In terms of companies, Issue 001 gave you a good framework for thinking about your work in terms of talent-company fit.
As for the specific job you do, there are two concepts that will most help create clarity. First is the personal hedgehog, a concept I adapted from Jim Collins’ seminal book, Good to Great:
And second is a clear understanding of the full context for what companies pay people like us to do. Every business has unique needs, but in general you can expect companies to need the following functions:
Get unstuck by doing one of these three things
When you know what you want, there are three ways to get unstuck:
- Change your current circumstances to create a better fit in your existing role (job crafting)
- Find a new role before you’re forced out of your current one (career search)
- Use your current job as an investor to start a new business (overlap)
1. Change your current circumstances
One of the biggest reasons people stay stuck is fear. They worry they’ll have to quit their job to start a company or start applying to jobs in order to find something new.
Sometimes all it takes is reframing your existing job — no scary leaps required. Academic researchers refer to this approach as “Job Crafting.” The first article on our essential reading list for this week defines job crafting as, “what employees do to redesign their own jobs in ways that can foster job satisfaction, as well as engagement, resilience, and thriving at work.”
This is in contrast to “job design,” which is the process a company or team goes through as they write a job description to serve the needs of the organization. Here’s the thing: many companies don’t 100% know what they need from a role before they hire to fill it.
A job description is their best guess at what is required to achieve the goal of the role. So long as you remember the outcomes you need to drive in your role, there is often flexibility to change the job to fit your strengths and interests. To do this, you can change 1) your day to day tasks, 2) your relationship to your boss, team, and customers, and 3) your mindset about the impact of your work.
The first essential reading dives into this more.
2. Find a new role
This is the most conventional of the approaches to getting unstuck. It can also feel the scariest. Once you’ve reached an impasse in a role — for whatever reason — I believe this is the most viable and responsible path for the future of your career.
If you’re not already, periodically perform “temperature checks” on your value in the market, whether you’re stuck or not. A temperature check consists of seeking out a competing offer of employment to help gauge 1) your ability to land gigs and 2) your market value.
Staying fresh with your job search skills means you’ll be ready to move when the time is right for your career, including when you’re stuck.
If you’re stuck right now, the image below gives a succinct overview of a typical hiring process at a startup. It includes what you should be doing at each stage.
This is what I made my workshop for — to walk you through the exact steps you should take to land the job that will get you unstuck.
If you decide to get a new job, do not spray applications to any company with an open role. It will take you forever to get a new job. When you do, that job will probably suck just as much as your current job.
The most important aspect of a successful career search when you’re trying to get unstuck: only apply to jobs with a high probability of getting you unstuck. This might look like 10-15 digital “coffee meetings” with interesting people at interesting companies and just 1-2 applications per month. Yes, it will take time! When you’re already stuck, why rush into getting stuck again? Instead, take your time.
3. Start a new business
It would be inauthentic to exclude this option from the list even though it can be a scary leap. I got unstuck by starting my first business and I run a company built on a mission to help creators (people running businesses) earn a living.
There are two things I wish more people would do when they decide to start a business:
- Become an expert in the topic of your business
- Keep your job until there’s a clear path to earning a living from your business
Here’s what typically happens when people start a business to get unstuck:
- Get stuck
- Read a book or blog post, listen to a podcast, or watch a YouTube video about starting an online business
- Quit job
- Start business without clear goal other than quitting job
- Business becomes a business about building businesses
The reason this path is so common is 1) people aren’t experts on anything they like enough to build a business around that expertise and 2) they need money because they already quit their jobs! What happens?
Because they’re enamored with the idea of building a business, they’re constantly reading about building a business. The easiest thing to do is to turn around and teach other people what you’re learning about building a business. It becomes a vicious and unsustainable cycle.
Instead, shift your mindset about the job you’re stuck in. If you know you want to start a business, your job has just become the best investor you could ever ask for.
All you have to do is give the job your best 40 hours every week to make them happy with your performance. Then you get to spend as many hours as you can stomach building your business.
This approach gives you the benefit of 1) time and 2) money. You can use time to build expertise and you can use your salary to pay your bills while you create a business model in your business.
Quit your job when your business income hits 50-80% of your salary and the thing holding you back from growing your business income is time.
This is a smart strategy that protects your downside (by maintaining a steady paycheck) and gives you unlimited upside (by starting a business with growth potential only limited by you).
The three most important things to read on getting unstuck
- What is job crafting and why does it matter? by Justin M. Berg, Jane E. Dutton, and Amy Wizesniewski – This is a perfect overview of the concept of Job Crafting from some of the original creators of the concept. It’s important to remember that the approach preceded the term — researchers simply uncovered it and gave it a name. Academics often have the affliction of writing in unreadable language, but this one is approachable.
- Linchpin by Seth Godin – I read this book in my last semester of college and the combination of the timing + the content changed my life. In order to have the kind of career opportunities that get you unstuck, first you need to understand what makes a person indispensable to a team or organization.
- Overlap by Sean McCabe – Sean wrote the book on using your current job as the investor for your new business. It’s a manual for starting a business on the side before going full time. If that’s the path for you, this is the book you need.
Don’t settle for being stuck
Too many people suffer through decades of being stuck in a dead end job. Tragically, careers like this often end in layoffs and trouble finding employment again.
You might be stuck right now, but that doesn’t have to be your future. To get unstuck:
- Reflect on how you’re doing every six months
- Identify *why* you feel stuck
- Get clear on what you want instead
- Take one of the three paths to getting unstuck
This approach takes self-awareness and courage. But what is the alternative?
Your career is too important to waste it doing work that doesn’t matter. Don’t stay stuck.