How to Invent Your Dream Career

Hi there,

I’m just getting back from a winter weekend retreat in upstate New York and feeling more rested, aligned, creative and ready to serve than ever!

We celebrated Imbolc over the weekend which is the mid-way point between Winter Solstice and Spring Equinox, which means we’re officially on our way to Spring! 

I’m already dreaming of resuming my Brooklyn Heights promenade walks. What are you most looking forward to?

Today I want to talk about a topic that’s near and dear to my heart: how to invent your dream career. This topic means so much to me, because for the first 31 years of my life I didn’t think it was really possible and I burned out as a result. 

Now, I believe it’s possible for everyone. So today I’m sharing: 

• How I invented my dream career over the last year

• The current conditions that make it more possible than ever for you too

• How to figure out what your dream career even is

• Steps you can take to start

Okay let’s dive in.

🌊 Where we go deep on a topic at the intersection of entrepreneurship and personal development.

 WHY I INVENTED MY DREAM CAREER

I invented and stepped into my actual dream career over the past year. Here’s what it looks like:

• I work with clients I am truly inspired by, and have the privilege of supporting their transformation, growth and progress towards more aligned work and life.

• I get to creatively express myself through writing, developing coaching programs and courses, designing my brand identity and website, and speaking on podcasts and at events.

• I’m continually learning and honing my craft in an area I already was obsessed with: personal development. I read books, take courses, and practice integrating my new knowledge and skills with my clients.

• I think strategically about how to build and grow my business, integrating my prior experience of building a startup and learning new skills along the way — from branding, marketing & selling, to strategy, operations & finance.

• I have the privilege of growing personally and doing my own inner work, with help from my own coaches, that allow me to show up as a better coach, with more presence, compassion, integrity, and devotion.

• I get to alchemize the pain of my experience burning out and moving on from my company into helping others find more alignment and less burnout in their own work and lives.

• I wake up most mornings feeling energized to go to work and I experience fulfillment as I get feedback on how I’m impacting the lives of my clients and community. 

It’s kind of a miracle.

And, it also hasn’t always been this way for me. I didn’t used to know that you could invent a dream career, something that is perfectly formed to the person you are, where you’ve been and what you’re meant to do.

As a young adult who was afraid of failure and wanted desperately to prove my value through achievement and success, I chose to get a business degree followed by a CPA designation — the exact same path both my parents took. I can remember in high school receiving the (logical and well-meaning) advice that getting a business degree is a good idea because every organization needs business skills, and so it’s a smart way to position yourself to be useful in whichever industry or organization you choose. I applied the same logic to my CPA: everyone needs a finance person. 

And then I became the finance (and ops, and growth, etc.) leader at The GIST. I was in a fast-growing, mission-driven company making an impact in a very exciting industry. But I still felt like “the finance person”. And so I still burned out badly, because logic and numbers and operations are simply not the full expression of what I came here to do. 

And look, don’t get me wrong, my business and finance background have served me immensely. I love business. I appreciate my financial literacy. And I also needed to go through that experience of misalignment to get to where I am now. 

I’m so grateful my burnout made me realize I didn’t want or need to exist in that version of myself anymore. And in fact I couldn’t. It would have just kept making me sick. 

And that’s what made me get serious, that it was time to invent my dream career.

HOW IT’S POSSIBLE FOR YOU TOO

Maybe you’re thinking “good for you, but that’s just not possible for me”. And honestly, fair enough. We weren’t modeled this possibility. We grew up with parents who, for the most part, did not have the world of possibilities we have today and where the smart choice was to stay in jobs for longer periods.

But the landscape has changed drastically and today there are so many amazing enablers to inventing your dream career. Here are a handful:

SOCIAL MEDIA & PERSONAL BRANDS

The internet & social media make it possible for you to reach millions of people with your message, your idea, your brand, your product or service. Where before people were limited to their personal networks, placing ads in print or out-of-home advertising, and local events, today we can build our own audience by showing up and creating quality content. This creates opportunities for marketing, selling, acquiring customers or clients, testing out ideas, creating aligned partnerships, attracting opportunities and developing a personal brand. (As someone who has built a multi-million dollar online business, and intends to do so again, I believe deeply in the power of this).

POWERFUL TECHNOLOGY

You don’t need a chunk of capital and a team of developers to bring an idea to life on the internet anymore. There are accessible, no-code solutions available for designing and building websites, apps and newsletters, hosting communities and courses, recording podcasts and videos, automating operations, acquiring and responding to customers, project managing teams — pretty much anything you can think of. And not to mention the impact AI is having and will continue to have on how this technology evolves exponentially. One person can now achieve what used to take the effort of big teams. At the very least, it’s much easier to test out MVP’s (minimum viable products) before investing big dollars in an idea.

REMOTE WORK FLEXIBILITY

A shift to more people working remotely part or all of the time has meant greater flexibility and autonomy over time. This means if you can get your work done in less than a normal workweek, you can open up time to work on new projects, ideas, and businesses. 

PORTFOLIO CAREERS

What this flexibility enables is a concept called “portfolio careers”, which is basically the premise that we can have more than one way that we express ourselves in our work/career and more than one income stream. Maybe you work a full-time marketing role and you have a roster of social media consulting clients on the side. Maybe you’re a founder that teaches breathwork on the weekends. Maybe you’re a health coach that earns extra cash through offering online courses. Maybe you’re an investor that also teaches at a college and sits on a non-profit board. Maybe you’re an operations manager with a podcast making money through brand partnerships. Maybe you’re an accountant by day and a DJ by night. Maybe you’re a lawyer that’s working on writing a political thriller. Maybe you’re a product leader that’s building their speaking career. Truly the avenues and combinations are endless.

WHY IT FINANCIALLY MAKES SENSE

There is typically an upper limit to how much you can earn climbing the corporate ladder at an organization, even if you are a truly outstanding individual and are moving up quickly. There is no upper limit on the amount of value you can create in your own business and you will own the upside. Owning this has the power to massively impact the wealth you are able to create in your lifetime.

HOW TO FIND YOUR THING

Okay, so perhaps now you’re bought in, or a least open-minded to this idea of inventing your own career. So where do you start?

Oftentimes we start with: what’s my business idea? How big of a problem is it? How big is the market for it? How much money can I make? These are all important things to consider. But this can be a limiting way of thinking and can risk us going into business in a way that’s not aligned to who we are and what we uniquely have to offer the world. (I initially did it the former way and it eventually burned me out). 

In order for this career to feel aligned to you, start by considering the following.

What brings me joy? 

If I had all the money in the world, what would I choose to do with my time? When do I feel the most alive and energized? What naturally piques my interest? What do I like to spend my time doing and learning in my spare time? What leaves me feeling in flow? When do I feel most like myself? 

What am I naturally good at?

(Not to be confused with what I have gotten good at because it was required of me). But genuinely, what gifts do I possess that come naturally to me? That people come to me for help with? That people compliment me on? (It might be something you take for granted because it comes so naturally to you). Think outside of the box on this one — it doesn’t need to be only things that would make sense on a resume, but that you apply in different areas of life.

What challenges have I overcome in my life? 

Often the adversity we face makes these areas personally meaningful for us. Maybe it’s overcoming burnout, or navigating coming back to work as a mother. Maybe it’s having difficulty raising money as someone from a marginalized group. Maybe it’s a trauma or limiting belief from your upbringing that you healed or overcame. Do you want to help others in any of these areas?

What unique perspective do I have from my life and work experience?

Maybe it’s where you’ve lived in the world. Or how you were brought up. Or what you studied. The groups and communities you’ve been a part of. Or the kind of work you’ve done, the impact you’ve had on organizations or individuals. 

Who or what do I want to impact?

What does the world need that I feel passionately about working on? (Not what you feel you SHOULD work on, but that you feel genuinely drawn to). How am I naturally drawn to serve others?

What do I need?

What do I need to feel good in my work?  Is it to creatively express myself? To have a positive impact? To learn and grow? To create something innovative? To collaborate? To work alone? To have flexibility over when and how I work? 

HOW TO DECIDE

Next is to think about how you use the answers to spark ideas and gently guide what you do. 

The important part here is to NOT look to models and businesses thta already exists, but to get creative about how you want to serve and create value for people. 

Any problem that people have can become a product or service you offer. Zoom body language coach. Restaurant marketing consultant. Gluten free pizza. Period underwear. Sleep trackers. The iPhone. These are things that did not always exist. If it’s a problem you’ve experienced, other people probably have too. And if it means something to you, it’s worth pursuing and at least testing out. 

There’s a woman in my coaching class who is combining her interior design skills with her life coaching skills in order to help people design their homes with an understanding of how our outer worlds are a reflection of our inner worlds. How cool is that?! Not a job I knew existed before then, because she probably invented it. But that sounds like an amazing service to me! 

Think about the way in which our society is evolving, and how people’s needs, desires, and pain points are shifting. Are there new problems emerging that will need a solution?

What would you absolutely love to spend your days helping others or the world with? 

As ideas start to come to mind, sit with these for a bit. Start talking about them to other people (who you know will encourage you), allow your mind to wander to how it could grow. See yourself doing it. Journal on it. Plant the seed and allow it to develop when you’re on a run or in the shower (or whatever makes you feel creative).

Some questions as you come up with the structure for your offering:

• B2B vs. B2C: do you solve problems for individuals or businesses? 

• Product vs. service: do you want to create and sell a physical product? Or do you want to deliver a service? Or a combination?

• Online vs. IRL vs. combo: Do you want to be able to run your business from anywhere? Or is serving or gathering people IRL a big part of what you do? Or some combination?

• Who specifically are you serving? Describe your ideal customer persona. What pain do they feel and how are you solving it for them?

• How will you make money? Is this a solution that enough people will pay for? How much will they pay? 

HOW TO MOVE FORWARD

INFORMATION GATHERING

You’re going to want to start by making a rough plan of how to go about doing what you want to do. And in doing so, you will probably realize that you don’t have all of the information you need to make your plan. This is normal. Start a list of questions about the information you need to gather in order to move forward, and then go about doing your research to fill in the blanks. You can check online, talk to people who have walked this path, listen to podcasts, read books, maybe take an online class. HOWEVER, for some, it can be easy to get stuck in this phase of information gathering and learning. Give yourself a limit of how much time you will spend here so that you know when it’s time to move into action.

It can be really powerful in this phase to seek out mentors, expanders and inspiration so that you can have examples of how people went about doing things, overcame challenges, and were thinking about things. When I was starting The GIST I listened to Girlboss, How I Built This, any entrepreneurship podcast I could get my hands on. This time around I made sure to have plenty of coaching expanders, mentors, and also took a coaching certification that provided guidance on how to actually set up a coaching business.

SET MISSION, VISION, VALUES

You did some great work on the reflection questions above around why you chose this idea. Articulate it in a mission, vision and values so that as you’re getting this off the ground, putting yourself out there, making decisions on how to move forward, you can be grounded in your “why”.

DEFINE WHO YOU SERVE AND HOW YOU SERVE THEM

Do your best to define who you serve. This is something that can sometimes develop over time as you see who you’re attracting. But you can start by going with your gut, and then iterating from there. This avoids you from falling into serving too broad of an audience. You’re probably heard “if you serve everyone, you serve no one”. It’s better to start serving a small niche very well and expand from there, than going in with a broad niche that doesn't’ feel as tailored. Write out what you know about them. What these people care about. What they want more than anything. What’s painful for them. How your offering solves the problem functionally and emotionally. 

And then go out and validate that information. Find real people that fall in your ICP (ideal customer persona) and ask them about their lives, about the area of pain you’re trying to solve. Try to avoid leading questions like “would you use this?”. The Lean Startup is a good read on this concept.

DEVELOP SIMPLE FINANCIAL PROJECTIONS

This doesn’t need to be an investment banker-level spreadsheet. It can be more of a back of the napkin style calculation when you’re just getting started. But you should consider how much someone would pay for what you offer. What’s the number of customers you could reasonably serve? What revenues could you conservatively expect? What are the inputs to your revenue? What will your costs be? What’s your upfront investment? Where is this money coming from? If you project you’ll be at a loss for a number of months, how long can you afford to fund your losses? How do revenue and costs scale over time? What levers do you have to increase revenue? Will you finance this yourself or seek external funding?

These are areas that getting clarity on earlier, and having a plan for them, will empower you. Remember, if you don’t know the answers, go out and find them. Do research and ask people who have started similar businesses.

SET GOALS AND MAKE A PLAN

Okay it’s time to set your goals! Your mission and vision can guide you. Think about where you’d like to be in 3 years? What have you accomplished? What has your impact looked like? What have your financial results looked like?

Now set your goals for one year from now, and break that down into quarterly milestones. Every quarter, decide on how you’ll measure those milestones and what tactics you need to execute in order to hit those milestones. For more details on goal setting you can refer to Setting Up for Success in 2025.

SET UP YOUR TIME

Decide when you’d like to put time aside for working on this idea. It can be as much or as little as you want. Perhaps it’s 30 minutes each day before or after your work (if you have existin work). A few hours on the weekend. Maybe you realize if you get ruthless at prioritizing your time, you can get your day job done in 5 hours a day or 4 days a week and you free up some time to work on your idea. 

Whatever you decide works best for you, carve out that time, and at the beginning of each week, plan which tactics you’ll tackle throughout the week. If a task seems too hard or intimidating, break it down into smaller steps.

PUT YOURSELF OUT THERE

It can feel really scary, but telling people what you’re building or creating is beneficial for a number of reasons. One, the probability of hitting your goals very meaningfully increases when you share them with other people. Keep yourself accountable this way. Two, people can’t engage with or promote your product or service if they don’t know about it. Your existing friends, family, and network are likely going to be some of your first customers and biggest brand advocates, so share about what you’re building. (Except for the people you don’t think will be supportive. You don’t need any of the naysayers life at this stage!).

Even if you’re not ready to announce what you’re building, start showing up online and in your community as a voice in the domain you’re building in. Start to build your authority, learn about your domain and share what you learn, share your opinion, tell stories about why this domain means something to you. Before I launched Within, I started talking online about burnout, healing, and building with alignment. So when I launched, I had already started to build an audience and people knew me for those topics. 

IF YOU WANT TO JUMP, JUMP STRATEGICALLY…

Over time, maybe you’re starting to see some traction, some success, perhaps some recurring income. Maybe there are early indications that you can grow this into something that fully supports yourself. Or use your traction to raise money. Maybe you’re feeling like you’re at the point where you want to go all in, you have strong indications that putting in all of your time would continue to propel growth. 

That is such an exciting place to be. AND, you want to make sure you’re setting yourself up for success. If you’re going to quit a full-time job or a meaningful income source, make sure you’ve saved 9+ months of your monthly expenses while you grow your income on your new idea. Or, consider scaling your full-time employment down to a part-time role, or freelance in an area you’re confident in while you continue building your idea. There are lots of different options available, the main thing is to make sure you have a plan to pay your expenses for longer than you think you need. 

… OR FIND A BRIDGE

In some cases, going straight from your current situation to what you feel is your ultimate destination, isn’t always the move. Sometimes you’re not ready. Not ready financially. Maybe you're not resourced well enough. Maybe you don’t feel you have the knowledge and skills yet. Maybe you don’t fully believe it’s possible for you yet. And that’s okay!

That’s where a bridge can come in handy. A bridge is an opportunity between where you are now and where you want to be. Maybe you work as a lawyer and want to launch your own startup, but you don’t feel ready. So your bridge might be working at a startup for a year or two so that you can learn the ropes and see what’s possible. Sometimes the more sustainable move is to take a step in the right direction rather than overhauling everything overnight.

GET SUPPORT

When you pursue a new business idea, open a more aligned income portal, or allow a new part of you to be expressed in your work, you’re stepping into a new version of yourself. It’s a beautiful and scary thing. It will force you to grow as you face new challenges. I highly recommend ensuring you have adequate support through this transition. Whether it’s an incredibly supportive friend group or finding new communities and mentors entirely, it’s so important to surround yourself with people who believe in you. You want people who can help you find all the reasons why you will succeed, instead of the people who will look for all of the reasons you will fail. It takes a leap of faith and you want to be around people who believe in the highest vision of what you can do and who you can become.

This is also why having a coach can be incredibly powerful. Having someone who can hold you to your vision, lovingly challenge you when you’re getting in your own way, and provide space for you to process the difficulties that come with the uplevel you’re going through, can make a huge difference. I’ve been working with an incredible coach through my own process of launching Within and it’s been an absolute game changer.

So if you’re feeling inspired to invent your dream career and you'd like a partner in ideating, creating your vision, planning, executing and overcoming limiting beliefs, I’d love to chat! This is absolutely one of my favorite things to coach people on so if you’re feeling the call even a little bit, let’s chat!

You can book a free strategic coaching consultation here. 

Alright, thanks for reading today! My hope is that you walk away from this email feeling inspired, energized and believing in the greatest possibility for what you can create and become.

🪞 Your turn to reflect. Take these prompts to your morning journal or talk it over with a friend or coach.

• If I continued on the path of my current career for the next 20 years, would I feel satisfied?

• What brings me joy?

• What am I naturally great at?

• What challenges have I overcome in my life? 

• What unique perspective do I have from my life and work experience?

• Who do I want to serve or what do I want to impact?

• What do I need to feel good in my work?

• What information am I missing that I need to get started?

• What is my mission, vision and values?

• Can my idea make money?

• How much time do I want to allocate to this? When?

• What small action can I take today to get started on this?

• How can I support myself in this brave endeavor?

🤿 If you want to go deeper than the deep dive, I curated these resources especially for you. <3

For figuring out what your thing is:

• Finding Your Own North Star and The Way of Integrity by Marth Beck

• Designing Your Life by Bill Burnett & Dave Evans

• What You Want to Do Is What You’re Meant to Do (an earlier newsletter by me, more on that fun exploration phase).

For inspiration

• Female Founder World podcast has so many valuable tactical insights from real founders on how they went about starting and growing their businesses.

• How I Built This - a classic.

• 1:1 Coaching: I have a few spots left for 1:1 coaching. Maybe you’re ready to move into a more aligned and entreprneurial career. Maybe you’re a founder who’s on the verge of something bigger and you want support leveling up in a way that feels good. Book a free strategic coaching consultation and let’s talk about it.

• Let’s be friends: If you want to see the BTS of building Within and receive more tips and ideas on building with integrity, connect with me on LinkedIn and Instagram.

Alright, thanks for reading today! My hope is that you walk away from this email feeling inspired, energized and believing in the greatest possibility for what you can create and become.

With love,
Roslyn 💚