On new beginnings


This has been both the hardest and most time-consuming post to write to date. I’ve been meaning to get started on this for weeks now, and I’ve only recently begun to find the strength to put my collection of complicated feelings into coherent words.

What proceeds is the final iteration of my attempt to condense the most tumultuous months of my life and introduce what’s next for me in a way that hopefully gets you as excited as I am for the future.

With every iteration, this post always came out a little bit brighter. In fact, the original titles of this post were “On failure”, “On failure and solopreneurship” and then “On failure and new beginnings”. Finally, we’re here now just focusing on the new beginnings. I hope you enjoy.

Since the genesis of this blog, I’ve prided myself in being transparent and an open book. I’ve shared intimate thoughts and feelings during my sabbatical, the financials behind my solo travels, and the mistakes I’ve made as an entrepreneur with Lunch Money.

Transparency leads to demystifying the unknown in taking risks and I’ve always been passionate about that, especially when I receive feedback from readers and peers that it’s been inspirational to them. Historically, this has always made the risk of vulnerability nothing short of rewarding for me.

However, this time, the vulnerability in sharing this post hits differently. It has nothing to do with my business or solopreneurship, and it isn’t related to stories of temporary travel or digital nomadism. It has to do with my personal life.

The intertwining of work and life in solopreneurship

It wasn’t until everything went down that I realized how intertwined my work and life are. In many ways, this seems like a bad thing. If you don’t have a work-life balance, the assumption is you never know when to stop working and you don’t take time to enjoy life.

But there’s a different interpretation with solopreneurship. At least for me, solopreneurship is a good fit because I want “work” to be a part of my life. It’s one of my hobbies and something I choose to do because I derive a lot of satisfaction from it and I find meaningful purpose in it. Working on Lunch Money, that is, developing new features, fixing bugs and interacting with users, was my major source of joy during the pandemic.

So when my personal life took an unexpected sharp turn, it brought everything down with it, including my work in solopreneurship, my online presence, and overall, my joie de vivre.

It’s important to me to convey that my sudden and recent absence is not out of neglect for what I’ve always been passionate about, but out of necessity for the recovery of my mental health so I can come out of this a better version of myself.

I’m going through a divorce.

(This is as close as I’m going to get to shouting on a rooftop at the top of my lungs as a form of acceptance.)

Sooo, long story short, almost overnight in September, I went from being what I thought was happily and securely married to starting divorce arrangements.

Heartbreak, shock, worthlessness, confusion. Just a small roster of feelings accompanying the roller coaster I haven’t been able to get off for the last 4 months.

All the interviews I did last summer where I was asked about my self-care routine or how I work efficiently as a company of one are all suddenly from a past life– one that I will probably never get back to. I’ve unwillingly and unexpectedly entered a new phase of life at a time when I felt more-or-less satisfied.

I have been (and am still) in extreme flux. It’s like I’ve been thrown off my trajectory and I’m now rocketing through space. I don’t know what debris I’ll hit along the way or which orbit I’ll eventually land in. My experiences in the last few months have been largely superlative– it’s been the most trying time of my life, the loneliest I’ve ever felt, the most purposeless, among just a few.

However, it’s not all bad! In seeking comfort and support from my friends as well as hearing from strangers on the internet and Lunch Money users who noticed my absence, honestly, it’s also the most loved and seen I’ve felt in a long time.

Reflections on my healing journey

To be clear, I’m not ashamed of my divorce and I am not going to let it define me. I am sharing my story for other people to understand who I am and to encourage others to do the same. Sharing our personal journeys and struggles brings us closer together and strengthens the shared human experience, which we need so badly in today’s climate. No one should have to go through the tough times alone.

None of what happened to me was under my control nor was it solely my fault, but it is on me how I choose to react and move on from it. I firmly believe in learning and growing from all of life’s experiences and despite the ways I’ve been knocked down, I am always going to choose to proceed with kindness and compassion, and continue to make a positive impact where I can.

So, what’s next?

One of the hardest parts with divorce is that 100% of future plans you made or envisioned for yourself and your (future) family dissolve immediately. Suddenly, my life is an empty and open field. Exciting? Sure, maybe eventually when I’m in a different headspace. Terrifying? Definitely. It’s got me asking fundamental and mind-bending questions, like, what do I want out of my time on this Earth? What should my purpose be? What parts of my previous life served me well and do I want to carry forward into my new life? What the hell do I do now?!

Most people have at least an anchor. A job that keeps them in a certain place. Family that keeps them within a radius. Property or a lease in a particular city. Pets with environmental needs.

As for me, I am totally unanchored, thanks to my already nomadic lifestyle and the freedom Lunch Money has afforded me. It’s both exciting and scary at the same time. I could literally do anything! I could move to Iceland, buy a van, and live in it for a year if I wanted to. But, well, despite living spontaneously and nomadically for the last few years, I’ve come to realize I’m ready to close that chapter of my life.

I moved to Los Angeles.

I haven’t lived somewhere for more than 1.5 years in the last 6 years. In fact, the last two places I lived in (Toronto and Taipei), I thought I would be for at least 3+ years. In 2020, the pandemic kept me from going back to Toronto after a planned 4-month trip to Taiwan. After staying a year and a half later, a rushed decision to head back to the US to get vaccinated meant I had to quickly leave an established life behind in Taipei, one that I had full intention to get back to. Needless to say, I no longer have a desire to return to Taipei for the foreseeable future.

There is a certain degree of trauma that comes with having the security of your home base being constantly withdrawn. Upon reflection, I am now craving permanence and control. Permanence to me means living somewhere for at least a few years and taking the time to deliberately put down roots to build a new life. Control means I solely get to decide where and when, and I no longer have to live with the fear of potentially not returning. I am creating my own security through self-reliance.

Moving to Los Angeles was the easiest decision to make. I knew right away I wanted to start my new life here, where I have a solid group of friends, year-round nice weather, a new city to explore and a bevy of foods to try. I see myself thriving here and I’m excited for everything else that comes along with that!

I am building a team around Lunch Money.

I’ve been feeling at a crossroads for the last few weeks. My whole dream for Lunch Money previously was to build a stream of passive income that I’d still work on as a hobby while pursuing other goals in my personal life, such as buying a house, settling down, having kids, etc. It was part of a grand plan to retire early and enjoy family life. Obviously, that’s out the window now.

The truth of the matter is that my personal motivation, while still there, has changed from the days of being excited to work on it 24-7. I have the financial resources and renewed passion to pursue other endeavors and I have a reinvigorated sense of purpose beyond Lunch Money.

That being said, Lunch Money has positively affected thousands of users so far and I have no intention of turning my back on them. In fact, it makes me more motivated than ever to continue pushing Lunch Money to its fullest potential by making it accessible and available to more people worldwide.

I am going to be building out a team around Lunch Money[1]. The first few hires will be engineers to help me with the backlog of bug reports and feature requests. I’m committed to finding a group of technical folks that work well together, believe in the product and genuinely want to see it grow.

So don’t worry, Lunch Money is here to stay. But what else is next for me?

Edited to add: I ultimately decided not to do this. I am excited to continue working on Lunch Money as a company of one and feel this is the best route for me to keep my lifestyle sustainable while keeping the quality of the product high!

I am starting a new company!

Over the last few months, I’ve come to truly appreciate the impact that Lunch Money has had on my life. By Silicon Valley standards, it’s barely a success story. It doesn’t make millions of dollars a year and there are no ambitions to take it that far.

Instead, it has reached a sustained level of stability and profitability appropriate for supporting my personal lifestyle. Along with that came a host of intangibles–it taught me grit, perseverance, and initiative. It helped my self-confidence immensely by dampening my imposter syndrome. It showed me what I was able to achieve on my own, and the influence that I, as a singular person, can have on a community of other builders, entrepreneurs and people interested in tracking their personal finance.

Having gotten to this point while enjoying the journey, working at my own pace and without the pressure of outside investors, would make me choose this path a million times over a traditional Silicon Valley career, joining an accelerator, or taking investment money to build out a business. In fact, those were exactly the paths I went down before pursuing Lunch Money.

What I realized while building Lunch Money in public and meeting other folks on the same path is that there is a gap in the industry to encourage and support more founders to stay bootstrapped and put their own needs and goals first. It should come as no surprise because in this case, only the founder wins.

Make the money, don't let the money make you. Change the game, don't let the game change you.

– Macklemore

Lifestyle business = an underrated path to entrepreneurship

First, it’s important we get on the same page about what a lifestyle business is, since there is opportunity to modernize the term.

According to Wikipedia, a lifestyle business is “a business set up and run by its founders primarily with the aim of sustaining a particular level of income and no more; or to provide a foundation from which to enjoy a particular lifestyle”.

This is inherently a different path from raising money or joining an accelerator meant to prep you for investors. Instead, a lifestyle business can help you reach financial freedom without venture investment and excessive administrative overhead that comes with running a traditional business. Staying independent (that is, not accepting investments and not giving up equity in your company) affords you the ultimate freedom of autonomy in all aspects of your business.

Ideally, a lifestyle business is set up to eventually run sustainably with minimal intervention. For all intents and purposes, we’re going to be focusing on tech-forward businesses, including but not limited to SaaS (software-as-a-service).

Introducing: Picnic Collective, Inc

Picnic Collective’s mission is to help and support solopreneurs and bootstrapped founders to stay independent while building their lifestyle businesses.

Picnic Collective is what makes the journey less lonely, while keeping it fun and meaningful. You, your aspirations and your business are the priority; investors aren’t even part of the equation. We care about sustainable growth and preserving independence.

How is Picnic Collective different?

Below are just a few ways that differentiate the Picnic Collective path to a lifestyle business over traditional means of raising money to build a business:

  • Sustainable growth over hyper-growth through investment money
  • Sufficiency over abundance
  • Preserving independence and autonomy over answering to someone else’s expectations
  • Maximizing free time and experiences over maximizing profits
  • See those who help us on our journey as peers rather than subordinates
  • Taking your time and enjoying the journey over racing against the clock to get to the next milestone
  • Collaboration and knowledge sharing should be meaningful and rewarding, not transactional

How can Picnic Collective help me?

Nobody has all the skills needed to run a business, and as solopreneurs and bootstrapped founders, we’re further disadvantaged by being limited in our time and resources. Identifying areas of need outside your experience is daunting and evaluating the caliber of a potential hire with a disjoint skillset as you is full of risks. Oftentimes, this is when one might feel like they need to give up equity in exchange for investors’ guidance, expertise and network.

Few people talk about the alternative, and I found that by sharing my own experiences with hiring as a solopreneur, it opened a lot of my readers’ eyes to what might be helpful to their own business (as they say, you don’t know what you don’t know!). What was obvious to my marketing hire to tackle first would have never landed on my engineering brain’s radar. And now that I was sharing this experience more widely, I saw that many other founders were inspired to start noticing their own blind spots.

The benefits of knowledge sharing are undeniable but can be elusive if, as a company of one, we’re not reading the right blogs, asking the right questions, or chatting with the right people.

I received a lot of help from within my network because I wasn’t shy to pick at my friends’ brains or ask endless questions when it was well-received. However, not everyone has the personality, the time or the network for this.

I envision a community of exceptional individuals, such as industry experts, subject matter experts, solopreneurs and bootstrapped founders, who are connected by a shared drive to redefine what work, retirement, freedom and financial independence means to them.

This will be a collective of highly-vetted folks forming a trusted community that can provide a host of resources to each other’s lifestyle businesses. It is where folks come for community and support on their individual paths to freedom.

What if I don’t have a business yet or I’m not sure if entrepreneurship is for me?

Picnic Collective doesn’t have a requirement of being a current business owner. If you resonate with our mission and you’re exceptional at what you do, we want you to join our picnic.

Since starting to build Lunch Money in public 2.5 years ago, I’ve sought help, support and advice from various friends and peers who were working in more traditional roles for an employer, but who were always happy to help as they got to glean the inner workings of my solo business. Understandably, they may be curious to learn more about the lifestyle to evaluate if it’s right for them.

There’s no way to sugarcoat it– entrepreneurship is not easy and it’s not for everybody. The leap it takes to leave the security of a job with benefits and a steady paycheck to pursue an unproven business idea backed by passion requires preparation. Being exposed in a variety of ways to the challenges, rewards and daily life of solopreneurship over time helps grease the knees.

If you’re an subject matter expert with working experience in a vertical such as, but not limited to, marketing, finance or engineering, and you’re curious about solopreneurship, one of the best ways to explore this path is by working closely with a bootstrapped founder who was in your position probably not too long ago.

Being connected to a pool of highly-vetted bootstrapped founders who like to move fast and who may be in need of your skillsets for a particular project or task will be an excellent way to try freelancing and help refine what your ideal work and lifestyle situations are!

Current status

Think of this as a manifesto. Details pertaining to specific services & offerings, pricing structure, and inner workings of Picnic Collective are currently being worked out and timely updates will be shared via the @picnic_inc Twitter account.

We’re all in on our mission and in the beginning stages of formation, so there may be opportunities to participate in discussions and share your ideas on how Picnic Collective is run!

Get involved

Sound interesting to you? Let us know through this Typeform, follow us on Twitter (@picnic_inc), or subscribe to stay updated on Picnic Collective.

Final thoughts

It is not that we have a short time to live, but that we waste a lot of it. Life is long enough, and a sufficiently generous amount has been given to us for the highest achievements if it were all well invested.

– Seneca

In life, we have two choices: run on autopilot and let life happen to you. Or, take the amazing and unique opportunities available to you only in this exact moment in time in our entire universe’s existence. I am choosing to actively find my meaning and do something that I can be proud of that makes every day worth living because despite life being difficult, it’s still pretty amazing.

If you made it this far, thank you for your readership and continued support and for allowing me to be open and vulnerable.

To the number of you who reached out, who barely know me on a personal level but noticed my absence with Lunch Money and cared enough to ask me how I’m doing, I truly appreciate you.

I’m still slowly getting back into the swing of things and clearly have a lot on my plate, but I am committed to getting through it all, slowly but surely. I apologize if there have been unanswered emails or calls– please feel free to follow up as necessary. I appreciate your patience!

Last but not least, a very special shoutout to my friends who took the time to read the various iterations of this post and gave me support along the way. You are all greatly appreciated: Jen, Helen, Richard, Bryan, Vrinda, Yannie, Jordan, DK, John, Mandy, Christina.

[1] Email jobs@lunchmoney.app if you’re interested. Otherwise, watch https://lunchmoney.app/hiring for job details in the coming days.

Thank you for your readership!

Jen is the founder of Lunch Money, a personal finance management tool for the modern-day spender. She is currently based in LA. Follow her on Twitter!

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👋 I send monthly-ish emails with updates on my solopreneurship journey.

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