michepriest

Daniel Vassallo (ex-Amazon) has a community full of people who have left or are wanting to leave tech. Several have been successful in creating info-products, courses, coaching, flipping micro-SaaS, etc

I got laid off from tech for the third time in August 2021. Decided I was done with it. Tried a bunch of things. Now I have my own “portfolio of small bets” (that’s the name of the community).

I take on 12 week co-founder for hire contracts where I do go-to-market work for 10 hours a week in exchange for base plus commission instead of equity. I learned to draw and have a couple of illustration contracts. I have a micro-coaching business where I help people get unstuck in 15 minutes with 3 questions. I’ve written some e-books. I also hold workshops where I teach founders and product managers how to put together their go-to-market strategies.

I love the flexibility. I own my time and can work on whatever I want. Downside was it was stressful trying to figure out what I wanted to do. In hindsight I wish I had enjoyed the journey more.

To see what’s out there check out the community. Look into creating courses and info-products. With your background you probably have a lot to teach. Also check out microacquire, Pencil Pirates, and Codie Sanchez’s YouTube channel. There’s a great book called Million Dollar, One Person Business. Follow Justin Welsh on LinkedIn.

I wish you all the best. Happy to answer any questions

I’ve used several pathways and got great results. Created several product prototypes of an ML model to see if there was a customer base and business opportunity for it. Ended up with a dozen potential license deals some with multinationals and a pilot expansion to over 100 locations.

Here’s what we explored:

Expert Network Companies - They connect you to the right people for a cost per call, $250-$1000 depending on their level.

I found my own expert (versus going through an expert network company). I paid her $350/hour. Well worth it as she built her network over 30 years and gave me hot introductions (she booked the meetings and was on the call) to first customers.

Leapmotiv - a customer discovery company. They’re great at booking cold leads and conducting high quality interviews. You have to be really clear on your goal. I recommend using them after you’ve done a few calls yourself so you have them working on deeper inquiry. Some of these interviews led to customer conversations.

DIY - LinkedIn

If you want to do it yourself I recommend approaching it like going to a new country. You need to know the lay of the land and be able to speak a bit of the language.

Read your target’s LinkedIn bio and job descriptions to see what matters to them. You’ll start to notice their lingo. Go for volume of calls and try speaking their language. They’ll feel more understood and thus more willing to give referrals for more people to speak with.

For example, I started a new co-founder for hire gig a month ago in a new space, health literacy. I kept seeing in the LinkedIn bios the challenge of getting patients to take responsibility for their own care. They use lingo like “health outcomes.” When I’m on calls, I get nods when I mention wanting to facilitate patient responsibility in their own care to improve health outcomes.

DIY - Online communities

This was where I found non-obvious use cases. Maybe there are forums you can join.

Podcast guest - Be a podcast guest on industry podcasts and let the leads come to you. Not sure if this one is applicable, but there are podcasts for just about everything

All the best! Happy to answer questions

I’ve had 7 careers (art teacher, financial advisor, owned an insurance brokerage, marketing director, intrapreneur, product manager, and a venture lead/interim CEO at an AI venture studio).

After my last job I wanted to quit tech. I spent 18 months trying a bunch of different things (no-code, podcasting, illustrating, creating info products and courses, E-commerce, and micro-coaching). I now do a variety of things including co-founder for hire where I not only advise but roll up my sleeves to get first customers and put together a data backed go-to-market strategy. The beauty of the co-founder for hire gig is it’s 10 hours a week. I get to focus on the things in tech that I love without the mad hours, politics, and stress.

The thing is, you can always go back to tech. Taking a mid-career gap year/sabbatical is an amazing experience. You’re sure to learn a lot about yourself. Tech isn’t going anywhere.

I’ve hit rock bottom a few times in my life. Once I was food insecure and another I was on short term disability for burnout. My latest period of strife is due to a traumatic death and a couple of near deaths of loved ones. I’ve done a ton of therapy, read self-help books, had executive coaching. What’s helped the most was deciding what I want my life to be, understanding the gap between here and there, then making incremental changes.

Regularly, throughout the day I remind myself that I am strong in my body. I am confident. I am a successful entrepreneur. Anytime a thought enters my brain stating otherwise, I pause and switch back to focusing on what I want.

What you focus on magnifies. You don’t have to believe every thought that enters your mind. You may feel empty in many moments, but I’m sure if you look hard you will find small moments throughout the day where you feel fulfilled like when you’re exercising. You also made it into a PhD program despite your dysfunctional upbringing. States of being are not binary so you don’t need to attach yourself to a state of emptiness and self-doubt. They can co-exist with other states of being.

It’s normal to feel stressed in a PhD program, especially toward the end. It’s also common for relationships to be impacted as graduate school is a transformative and demanding experience.

Keep going, keep your head up, and be kind to yourself. Replace self-doubt with self-compassion. There’s a new and exciting life waiting for you. By this time next year, this will all be behind you.

When I got laid off for the third time, I decided not to go back. We sold everything (house, rental property, cars, business) to have more freedom.

I took a bunch of courses, tried a bunch of things, joined a community of people wanting to create streams of income (Portfolio of Small Bets), did some freelance work, created info products, and conducted workshops.

I’m now a co-founder for hire where I take on 12 week contracts to help founders with their go-to-market and get early customers. I’m planning on holding a cohort based course for people who can’t afford my contract rate. In addition I have a few side projects with others (create courses and newsletters).

What might help is thinking through the worst case scenario and putting guards in place. Come up with as many ways as possible to earn income quickly and see what’s the fastest way to test those ideas. Pick a few and commit a few weeks to a month to execute. Then examine the experience and see how you can iterate to improve the outcome. You’ll want a mix of things to improve your odds of surviving and not having to go back to corporate.

There’s no better incentive to succeed than the desire to avoid your time being owned by a corporation. It seems to me your drive is there. I wish you all the best on your journey.

Why - I got laid off from a job I absolutely loved. I loved my team, the project, the company. I felt like I found my calling, building software with AI to provide immediate benefits in a meaningful way. I didn't mind the high pressure and intensity because I got positive feedback from users and potential partners multiple times a day.

Then two weeks after everything took off (1400 users to 72K users, pilot expansion to 100 locations, a dozen potential license deals, international media coverage), I got laid off. I took it way too personally and got depressed. I decided I’d never pour my heart and soul into someone else’s project ever again. I was done with tech.

Income - I knew I didn’t want to be an employee. I needed time to figure out my next steps. We sold our house fully furnished, sold our rental property, sold our cars, and sold our business. We scaled back our living to be able to live on one income. After a year I took a couple of freelance gigs.

Benefits - Deeper relationships with everyone that matters. More time for spouse, kids, family and close friends. I learned how to exercise for the sake of exercise. I did a lot of therapy and meditation and learned how to manage my expectations, be kinder to myself, and stop assigning meaning to things that don’t matter. I realized all the things I wanted, I already had.

Projects - I took a year and a half off. In that time I took a bunch of course and joined a solopreneur community. I wanted to figure out how to have work fit my life instead of the other way around. I did 100DaysOfNoCode and built over 15 apps and websites. I took Pencil Pirates and learned how to be a digital illustrator. I made 30 podcasts in 30 days with Espree Devora’s cohort course. I made info-products on Gumroad (e-books and an online course). I delivered a virtual workshop and set up an Etsy store. I tried drop shipping. My favourite project is Unstuck in 15. It’s a decision making framework I developed that helps people get unstuck in 15 minutes with 3 questions. I have a potential deal to license it through an educational institution.

Return to old job - Nope, but found my way back to tech in a way that works for me

Do anything differently - I wish I would have enjoyed the journey more. I was so focused on trying to figure out my next step that I caused myself a lot of undue stress.

Bad - I didn’t expect it to take so long for me to figure out what I wanted to do next (co-founder for hire). It would have been good to have more frequent and open conversations with my husband about this journey. I’m fortunate that he believes in me and sees the potential for a better future. We’ve always been able to grow together so we were able to weather the storm.

I’m happy to answer any other questions

Sounds like you might need more information on both of your options.

It might help to write and respond to:

What are all of the ways I can stay motivated and productive while living with my parents?

What are the worst case scenarios with both options, and how can I overcome them?

What are all of the ways to ramp up revenue/income faster so that I can have more options?

What does “being managed out” mean/look like?

This isn’t answering your question, but I thought worth mentioning based on the concerns in the comments.

One way to know if you might be getting laid off is when your 1:1s stop happening. Your manager might make excuses for skipping that week, then the next and the next. They also seem to have a change in personality.

Another way is if you feel the goal has changed and the new goal is ambiguous.

I’m currently drawing illustrations for a course to help employees navigate layoffs. It suggests ways to get visibility into what’s happening at the org, factors that impact lay off decisions, and how you can place yourself in a position of strength.

Basically get as much info as you can like an investor would about the company’s performance overall. Understand how your specific team impacts the bottom line. Make sure you’re performing well and it’s viewed that way. When it’s time for layoffs, your manager is looking for reasons to justify letting you go. When they have that lens on, anything can be misinterpreted.

If you feel you may be getting let go, it’s better for your mental health and your ability to get the next job, to leave on your own terms.

This isn’t advice that was given to me but something I wanted for myself that changed my life.

Advice: Figure out how to exercise for the sake of exercise

In the past I exercised for a weight loss goal. I’d reach the goal then stop exercising. I spent all of last year experimenting trying to figure out how to be like those people who run in -20C. I wanted to love some type of exercise so much I’d do it in -20C.

I’m now training for a marathon. I look forward to running and get excited about hill training (running up and down a hill at moderate exertion). I find running enjoyable and meditative.

The lessons I learned I apply to other areas of my life. For example, when my brain initially rejects something I know is good for me, I think “not today” and put on my running shoes (ie do the thing).

Learn how to ask great questions in a way that generative. This will help you catch issues early. To do this pay attention to people asking great questions that are well received and surface issues without causing a lot of tension. Break them down to understand why they’re effective

Aligning your activities with the company mission is great advice.

“bosses will give you tasks which are about furthering their career”

This is obvious but hadn’t occurred to me

I spent last month trying as many things as possible to see what was most desirable. Best paying ended up being trading time for money. In order of most money made:

• workshops • custom illustration packs • microcoaching • online courses • ebooks • merch on Etsy • Upwork gig

I’ll be working on converting residue from time-for-money projects into products. For example, I’m turning my workshops into online courses, my illustration packs into icon bundles to sell as digital products, microcoaching as asynch videos, online courses transcribed into ebooks, and concepts from all of them into merch (coffee mugs, journals, t-shirts) with an ability to mix and match bundles

I started all of this when I got laid off. I ended up needing flexibility to take time off to help my family so can’t see getting a full time job anytime soon. I’m also done working 60-80 hour weeks for startups and can’t figure out a job that pays enough that’s low stress. So scrambling to make this work

Interesting question. I’ve felt lost most of my life but haven’t consciously thought of trying to overcome the feeling itself. Lately I’ve been looking at humans and animals as all not knowing why we’re here but doing stuff anyway and wondering why and what’s the point. I’m exploring the idea of the point being to just be and if that’s the case then how can I be the most alive in any given moment. I’ve been examining when I feel the most alive and how to have more of those moments. For you it seems you’re unable to identify those moments but you mentioned you have had a few highs. I wonder if that’s a good place to start. Whatever you were doing leading up to those moments, do more of that. See what’s tangential and explore from there. As others have said, you’re not alone. I hope you figure out ways to have more moments of feeling less lost

Questions Are the Answer by Hal Gregersen

When you’re stuck or your team is stuck, do what he calls a “question burst” to ideate all the questions that need to be asked. It’s so simple but highly effective

It’s an experiment. Many people are trying to figure out a way to make a living that doesn’t require giving our time away to someone else. As much as I’m sharing ideas, I’m looking for ideas for how to stay self employed longer so I can support and be there for my family. My mom lost my dad, and my children lost their dad. No employer would have given me/will give me the time off I need

Thank you. I’m happy to share more information. It’s a framework that’s been developing organically tying in my work/life experience and masters research.

There are 3 ways people get stuck. 1. Trying to force an outcome on one solution. 2. Thinking in the binary with option A and option B. 3. Too many options.

Once the pathway to being stuck is identified, there are 5 categories of questions that get people unstuck. 1) Widen the lens - explore all of the options 2) Missing data - people can get stuck when they don’t have enough information about their options 3) Risks - When people know their options and the details but haven’t considered all of the risks 4) External factors - usually disagreeing with an authority figure such as investors, stakeholders or parents and partners 5) Internal factors such as lacking confidence

The constraints of 3 questions and 15 minutes forces me to ask high caliber questions. I don’t need to know the answer. I just need to figure out the questions to ask. You may not reach a decision, but you will have clarity on the next steps

I joined a group called Portfolio of Small Bets by Daniel Vassallo. It’s an online community in Discord full of people doing all kinds of projects. The majority are devs. There are channels for marketing, lifestyle, meetups, small wins. The premise is to design work to fit your life

I’ve met many interesting creators there. Some build software, many create info products and courses, and some make and sell physical products. The community is full of top tier creators so great to learn insider tips

There’s that saying, “a healthy man wants a thousand things, a sick man only one.”

I burnt out so badly I was on short term disability for 3 months. If your health is declining, it’s not worth staying.

That sounds amazing! Congratulations

Do you still want to be a data engineer? I wouldn’t let HR “requirements” stop me. There must be a way. 5+ year DEs once had 0 experience

I started in finance and got into tech. Was a product manager. After my last lay off I decided not to go back to being employed.

I’m creating info products (ebooks, online courses, digital products) and doing micro-coaching (unstuckin15.com). I love that I own my own time and can create whatever I’m inspired by.

I highly recommend mixing with freelance work in the beginning until your projects cover your income. If you explore this, join Daniel Vassallo’s community. It’s full of solopreneurs.

With your background there’s probably tons of products you can create.

The fastest way to leapfrog your career is move to a new challenge every 12-18 months. The moment you’re stagnant, leave. You can be in a challenging environment at one company, but this doesn’t sound like one of those companies. Their issues are likely systemic. You’re right about losing your skills.

The only thing we can’t make more of is time. If you’re not willing to risk another year hoping, it may be time to move on to the next challenge

I’m living it now but didn’t realize it until recently. It’s easy to focus on what we don’t have and want something else. I came to this realization when I kept getting everything I worked for but then was on to the next thing. When I was 20 I never could have imagined the life I ended up living (in my mid-40s now).

After getting burnt out in tech startups 3 times I made a change. Sold 95% of our worldly possessions in order to have the flexibility to live anywhere. I get to spend my days drawing, writing, creating info products, and helping people get unstuck.

Sometimes all we need to do is look at what we have, figure out what we want, and get rid of the rest.

This is a perfect Unstuck in 15 question. Unstuck in 15 is a framework to get clarity in 15 minutes with 3 questions.

The first question could be: What are all of the options available to you?

You have move and change careers. One might be working in a lucrative job and creating side projects. Another is exploring different industries and seeing what those job titles are. They could be something unfamiliar such as “intrapreneur”

The second question could be: What information is missing about your options? You’re doing a bit of this by asking about tech jobs.

I worked as an AI product manager. There’s tons of opportunities in AI. If you’re wanting more strategy work look into becoming a product manager (not to be confused with project manager). Although I suspect you’ll eventually go back to wanting to build. Strategy is mostly stakeholder communications and negotiation.

The third question is always nuanced and depends on the person and situation. In this case it might be along the lines of: What are all of the ways you can advance toward a career in product design despite the constraints?

There’s voluntary apprenticeship, making things and sharing your process on social media, creating lucrative Udemy courses on product design…

I had a manager who was exceptional during the time she was allowed to lead. Later she got a new manager who micromanaged her so she lost effectiveness.

She was curious and had excellent listening skills. She saw the best in everyone but was quick to address issues in a kind and humane way. She saw her job as purely removing roadblocks. She trusted us to be experts in our domain. She was adept at navigating stakeholders and getting us what we needed.

As far as books goes, aside from The Path Made Clear, read those that help you go deep into whatever it is you’re exploring so you can quickly get over the discomfort of learning something new.

If you’re over 40, read From Strength to Strength. If you don’t already, learn to meditate. There are many different methods. Find one that feels right for you. Move your body in the way you naturally wanted to as a child. For example, I loved riding my bike and doing cartwheels so I bicycle and do yoga.

I recommend Meditations of Marcus Aurelius. The next book on my reading list is Soulcraft by Bill Plotkin.

As far as happiness, it’s not a destination. It comes in moments. You have happiness. We all do. The trick is to be present when it happens. The key to happiness is decreasing the moments of unhappiness, learning how to let go. A mentor of mine told me to figure out how to only give 1 fuck a week. It changed my life.

Journal, analyze what brings you moments of unhappiness and structure your life to eliminate as many of those as possible. Write what brings you more moments of happiness and how to increase those.

I’ve been working intentionally on this for over a year after I got laid off and decided I didn’t want to work for someone else again

The best explanation in what I’ve read is, purpose is “living the truest expression of yourself as a human being” - Oprah

To get there I recommend her book, “The Path Made Clear.” Go through it slowly. Your path will unfold in parallel.

I’m working on living authentically (saying what I need to say in the moment not thinking of it after the fact) which is needed to find and live your purpose.

Tactically, at its core, the first level is getting your basic needs met. Beyond that, it’s figuring out who you want to serve and how to use the gifts of your personality to serve them in a way that’s fulfilling to you.

In my year off I took many courses and read many books. 100DaysOfNoCode.com, 30 podcasts in 30 days, Pencil Pirates, Hassan Osman’s course creation course, Decafquest’s philosophy course. I recommend following your curiosity and taking courses that pique your interests. Through this I discovered I could draw. It’s been therapeutic and useful in many ways.

I’ve found my purpose, now I’ve got to figure out how to make a living off it. My purpose unfolded organically. I tried to ignore it because I couldn’t figure out how to make a living off it, but it kept coming up. It brings joy to myself and others. It’s something I couldn’t have figured out by following someone else’s path.

My purpose is to help people get unstuck. I can do it in 15 minutes with only 3 questions. The framework I developed evolved organically. There are 6 categories of questions to help people get unstuck. People love the sessions. Seeing them start with concern or uncertainty and end with relief and confidence is the most rewarding experience for me.

I wish you all the best on your journey

Own my own time

I have a friend who felt similar about CRUD apps. He quit and got some freelance work while working on a couple of micro-SaaS products (check out microacquire for ideas). He then stumbled onto some web3 projects. Found one that got him super excited. Started working there part time. Brought some dev friends over. Then wrapped up all his freelance and other projects to go all in on web3 as a full-time employee. He gets to work on challenging tech with his friends

Not sure if this helps, but there are a few ideas to explore

My son is a full time, employed dev who negotiated working 30 hours a week so gets full benefits. He sticks to it. Seems everyone accepts he won’t put in additional hours. Has time to pursue other things.

I’m part of Daniel Vassallo’s Small Bets community. Majority are devs who quit or plan to quit and generate income in tons of different ways (digital products, micro-SaaS, real estate, freelancing, e-commerce, content marketing, domain flipping, YouTube…). Might be worth checking out