Ask JF: Leap And Pray or Build On the Side?

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Because of my somewhat public evolution from lawyer to serial entrepreneur, blogger, author, speaker, producer and beyond, I’ve been asked one question more than any other…

Should I quit my day job and go all-in on my passion, or work it on the side?

I’ve interviewed hundreds of people who have made major midlife career shifts from larger organizations into the wacky world of entrepreneurship. My personal approach has been much more leap, scramble and work like crazy to succeed (or not, lol) before my money runs out. But there’s also a strong lifecycle connection to the approach you might consider.

The further you get into life, the harder it is to execute the “leap and pray.” Click here to tweet this

You have more responsibilities, more to lose, and the perceived pain of failure becomes a bigger emotional and psychological barrier. Not to say that it cannot or should not be done, just that the trappings of inertia become harder to release with age.

The way most adults with responsibilities (and without big cushions/investors) do it is to:

  • Keep the main gig strong and
  • Work the passion job on the side

Question is how long do you do this? Answer – until one of three things happens:

  • Until it’s swappable – The passion project reaches a point where it’s generating enough cash to essentially make an even swap with the day job.
  • Until it’s projectable – The growth and revenue trajectory is becoming clear and consistent enough to make you believe that the passion project will go where it needs to go within a short enough window to be covered by a cash reserve. Then, you take a leap of faith once it’s most of the way there and work like crazy to make it happen.
  • Until it’s untenable – You learn that your initial assumptions were wrong enough to make the project untenable. At that point you either need to walk away or explore whether this new information is giving you a new roadmap for success a different way. And even then, you need to ask whether that different way will still still excite and inspire you. It may make the venture financially viable, but will it still be soul viable?

When I was working on Career Renegade, I interviewed an orthopedic surgeon who took 20 years to build into his next career as the founder of Kona Joe coffee in Kona, Hawaii (that’s Joe in the photo above). It would have taken longer, but he had to go all-in to raise the money needed to take the passion project to the next level. He was still travelling back and forth from his home in Orange County, CA where he still practiced medicine, to Kona.

To keep growing Kona Joe, Joe and his wife, who is his partner in the business, needed to buy some big equipment that would have to be financed by selling their house in California. That would essentially mean the end of Joe’s practice. It was a tough decision, what I describe in Uncertainty as a creation “crux move.” The choice you make in that one moment defines a cascade of major outcomes moving forward. This was a make or break moment for Kona Joe. They sold. And never looked back.

One other really important point here – keep your lifestyle in check along the way.

Once the passion project starts making a bit of money, if at all possible, do not raise your living expenses to consume that extra income. Bank the money instead. Because if you ratchet up your lifestyle to consume all of the income generated by both your main gig and your passion project, when it comes time to make the leap, you’ll end up earning only half what you now need to live. Bad math. Bad move. And the anticipated pain may well be big enough to keep you from ever making the jump.

So, what do you think? And for those of you who are building something on the side right now, what’s your leap plan?

Share your answers in the comments…

P.S. – If you’d like me to answer YOUR question in an upcoming “Ask JF” column, go ahead and ask your question in the comments below and you could show up in a future post.


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55 responses

55 responses to “Ask JF: Leap And Pray or Build On the Side?”

  1. Interesting post, and refreshing to see this type of discussion covering people over 25. I am a little over 40, have 3 young children and everything in terms of financial commitment that goes along with that. I run a start up which is so far unprofitable, and am at a cross roads of a slightly different type: do I carry on full time trying to build my dream and my fortune, or do I take something less secure and dilute the time/energy I put into my start up business? the question is complex as the financial uncertainty and stress is impacting on my life in a negative way, but I am convinced of the need to be single minded when getting something potentially big off the ground. This is an emotional position rather than one based on evidence or data, and maybe wrong, but it’s what I feel. To share my experience of leaving a safe job (the BBC in my case) and starting out on your own I’d say make the leap – necessity is the mother of invention and whatever happens, this type of decision gives you incredible momentum and will change things in ways you are unlikely to be able to predict.

    • Jonathan Fields says:

      For some people, clean breaks and leaps are definitely the way to go. For others, the pressure becomes a paralyzing force. A large part of it also has to do not only with life-cycle and responsibilities, but the mindset you bring to the endeavor

  2. Kristin says:

    I got really lucky and discovered my purpose at 19. I love my work/career/profession and I am doubly lucky that I get to practice acupuncture part time AND take care of my 2 little girls. I guess you could say I have it all. But it would never be possible if my husband didn’t provide us with our charmed lifestyle by working a job he is good at but doesn’t love. I look forward to the day when I can be the bread winner so my husband can have the luxury of making his passion his life’s work. I think we are building on the side now so that we can leap and pray later.

    • Jonathan Fields says:

      It’s often a dance between balancing “who gets to be really happy” with families and careers, but ultimately if you both aren’t really happy, it takes a toll on health, mindset and relationships. So, it’s really important to keep your finger on the pulse of both partners’ fulfillment on a regular basis

    • John Taylor says:

      Hi Kristin Really like your comment regarding you and your husband, our relationship has been very similar with me been the main bread winner for most of our marriage. My wife has now got her degree and changed her career so now that making the leap far less of a worry for me.

  3. I have seen many start their passion on the side only to give up because it felt like it would never work into a full time thing. Personally it felt like they were playing small. Jonathan some have passions and do not have the entrepreneurial dna. Running a business VS begin an employee are two such different skill sets.

    I liked your advice on the lifestyle. My vision was to create my lifestyle as part of my business. Being able to deliver my services or products no matter where I was, traveling, visiting or playing. I had disliked being chained to a brick and mortar location.

    Imagine when we have everyone living a soul, lifestyle, prosperous supporting business. Now that is a world I want to play in.

    • Jonathan Fields says:

      You’re probably right, some folks may not have the entrepreneurial DNA. But I’ve also found that it’s less about DNA and more about skills, self-care and developing the trainable mindset skills needed to thrive in uncertain environs

  4. Absolutely as we age, inertia means we don’t leap as far.
    Or perhaps we leap with more confidence because we have done it before.

    So it doesn’t appear to be such a big leap, when in fact it’s a much larger one when you factor the increased responsibilities.

    I love the question of the ‘right time’ to quit the day-job and leap.

    I think a very common scenario is when the day-job becomes to painful, or too toxic and stops you from working properly on the side-hustle. Then you have to make the move, or risk destroying both.

    • Jonathan Fields says:

      For sure, there may well come a time where you simply cannot take the toxicity of the main gig any longer and then it’s more a matter of mental and physical health

  5. That is some seriously good advice, Jonathan. Perhaps this post contains the seeds of your next book?

  6. Paul says:

    Jonathan, I’d love to know how many people are asking themselves this exact question today? I bet we would be amazed by the answer. I just read another article just last week about this exact same topic. Perhaps you might find it interesting (disclaimer, I have nothing to do with the article):

  7. YamaGma says:

    I like today’s lesson allot. And it applies
    to making decisions about changing
    residences as well. Good advice!

  8. Karlotta says:

    Hi Jonathan! I’m on the build-on-the-side path with a plan to take a leap of faith at a pre-determined time. The pre-determined date helps me keep motivated and stay focused on the goals that I’ve set for my company. The ultimate plan is to get out of the day-job as quickly as possible as it is becoming painful and toxic and I’d like to leave on good terms.

    • Jonathan Fields says:

      No doubt, having a fixed leap date to work backward from can help ensure you keep doing the work everyday.

  9. I am in the position where I will not abandon my day job which I built from scratch to pursue my other passions until I see that they might payoff. I’m in my early 60’s and am looking at other things to pursue; I still have plenty of juice left, but juice has to be conserved. I’m in the age group where I am planning where I want the rest of my life to go now that the first half is over. I love this blog and find myself trying to bridge a possible age gap. This was good practical advice. Maybe I’ll a JF to the AARP set.

  10. Tammy L. says:

    Thank you so much for this dose of reason. I am someone that wants to jump at new activities. I go all in. Then I realize that either it’s not for me or there isn’t enough of a market or (insert hundreds of other issues here). By keeping my day job and working things on the side, it is self-imposed patience that allows me to more fully think things through.

    • Jonathan Fields says:

      It also allows you more breathing room to try experiments, fail, correct course and learn without freaking out as much when things don’t go according to plan, and they never do

  11. Great post. For me the decision was easy. My employer objected to my non-competing side-business (unreasonably in my opinion), which resulted in them firing me. I’m now 2 months in, I’ve never been happier and never looked back! I’m about to become a Director in a 2-man technology startup and life’s good! So the moral is: even getting fired isn’t necessarily a bad thing, as long as you’re at least partially prepared to run your own business already.

  12. Jon Wilburn says:

    Jonathan – It’s posts like this that gives me the confidence to move forward with my side project and true passions. I’ve failed a few times with blogs and other projects, but I don’t think I was doing the right things. For me it’s building on the side, but the hustle is what’s going to get me there. I appreciate your insights.

    • Jonathan Fields says:

      When you’re starting out, think of it all as a series of learning experiments, focus more on the learning than the need to succeed

  13. Hey Jonathan – glad to see that there are people who will recognize that going all in isn’t an option for everyone, nor is it the only way to succeed. When you have kids, health insurance and a mortgage, you still have passion. It just waits until the kids go to bed.

    • Jonathan Fields says:

      I know a lot of entrepreneur parents who work the 9-12pm shift. lol

  14. Mike J says:

    Great comments – and exactly what I have been thinking about. I am in my mid-fifties, well established, have almost enough investments to effectively “retire” (which to me means working is an option, not a necessity). I recently talked to a young pair of entrepreneurs just out of university, and they were going totally gung-ho on a start-up. To me, the financials and market were not there, or at least not enough to jump in full time, but for them, it was perfect. Why? Because they had nothing to lose! No assets, no family life, they were just starting and could risk it all – how much are they actually risking?? Would I risk my current position for a passion? That is a big question.

    So doing it on the side is another way to reduce the risk – but as you get older, your energy and the ability to burn the candle at both ends goes down. Can you put enough energy into the new venture to make it actually work on the side? Certain ventures also cannot be done on the side – like Joe’s coffee, to continue it required a move from on-the-side to full-time – no choice in the matter.

    I am currently holding a full time job and doing a venture on the side – and it’s wearing me out. So the “crux” may come soon enough – choose the safe way for a few more years at something I am not passionate about (but generates good income) and then try again (being free from having to work for money), or go full bore right now. That decision will require a lot of thought to make.

    Good thoughts and discussion – I always enjoy your ideas Jonathan!

    • Jonathan Fields says:

      Great points, also check out my response to Lynn Hess about self-care, the missing element for many entrepreneurs

  15. Absolutely!!! Especially about keeping your lifestyle in check!

    It would actually be a good exercise to start this one before the passion project starts…We have a tendency of accumulating stuff (Yes, I speak from experience:)). We feel valued and define ourselves in the stuff we own. In reality, a valuable lesson I have learned, is that we do not own all this stuff, it owns us! We invest so much time, energy and effort in maintaining it that is consumes us from doing the things we want. I have worked with many individuals who, believe it or not, get this, have told me, “My passion is to start my own catering business, but, I know that my quality of life would change for about 2 years before getting started!!” These people are talking about having to get rid of some of the fancy stuff in their lives…REALLY????

    The day I realized that everything I owned was coming in the way of what I really wanted to do, I got rid of it. You know what? NOTHING bad happened. Actually I experienced and discovered so much more than I never knew existed because of it..Don’t miss it, not even a bit!

    This is one is GOLD, Jonathan!

  16. Denise says:

    Great advice. My business partner (husband) and I plan to live on his income while I work full-time and he works part-time on several projects. We hope that we’ll be able to generate enough to live on so that he can eventually stop working for the big corporation. If not, it will at least be additional income and our time will be better spent.

    • Jonathan Fields says:

      That’s a scenario I’ve seen unfold so many times and it can work really well. Just be absolutely sure to keep very strong lines of communication open about expectations and effort over time

  17. Emmanuelle says:

    I’m 35, quit my day job last week, and I am now proud to call myself a full time yoga teacher and life coach. It was not swappable, it was not untenable, it is projectable, and I will add another one: it was necessary for my sanity. I have built this slowly, making mistakes, making good moves, and learning. I am still learning and yes, it will take some time before it truly takes off, and that’s where trust and hard work shake hands 😀

    • Jonathan Fields says:

      Congrats on the leap, so glad to hear it’s proving your intuition and projections out!

  18. Bozidar says:

    It seems that “ownership” is a concept that is standing on the way of true entrepreneurship – the more you “own” the less likely you are to take the leap of faith and leave the permanent job to launch your new venture. That’s why I like your advice of banking the money and now proportionately spending. Thanks JOnathan and keep up with great books

    • Jonathan Fields says:

      That’s definitely part of it. But the bigger thing is not what you own, but who you feel you’ve made promised to, both spoken and unspoken, as you move further into life.

  19. Lynn Hess says:

    I really admire people who have the energy to work a full-time job, spend quality time with family, and still run a side business. I’ve tried that, but it has never worked for me. The side business never gets much traction because I don’t have enough of myself left to give it. So I have always been a big, dramatic leaper.

    “Leap, scramble, and work like crazy before my money runs out” has worked well for me a couple times and not so well one other time — and I’m getting ready to jump yet again. Who knows, maybe I’m addicted to the adrenaline? More likely, I’m just one of those people who has to be forced out of procrastination by not leaving myself any other option but to move forward quickly and decisively.

    Luckily I don’t have a very luxurious lifestyle to maintain — having to stop eating out for a while is going to be the hardest part!

    • Jonathan Fields says:

      One of the single most important, yet most neglected thing for aspiring entrepreneurs is also a dogged commitment to self-care. Meditation, movement, vital nutrition and time to pause are mission-critical in building the reservoir needed to sustain the side-hustle long enough to see if it’s capable of turning into the main hustle.

      • Lynn Hess says:

        Absolutely! And, unfortunately, those things are often the first things to fall by the wayside when one’s brain is freaking out about “not having enough time” to do everything. Reminds me of the quote (supposedly from Gandhi)that “There is so much to do today. I must meditate twice as long.” Good advice!

  20. Rob says:

    Rockin’ stuff, Jonathan.

    A burning question for so many people! Thanks for sharing your thoughts so concisely and clearly.

    The advice about keeping your lifestyle under control is so important, I am learning. New ventures have their ups and downs and from a material point of view, I have learned the more you own the more it owns you so when things get tricky there are more decisions to be made when you only to be making a few.

    There is a lot to be said for taking big leaps earlier on in a (less responsible) entrepreneurial life and bigger, yet more calculated, leaps later on in this life.

    In the same way you would perhaps invest a greater proportion of money in stocks and shares in your twenties and a similar proportion is lower-risk assets in your fifties.

    • Jonathan Fields says:

      Nice analogy with the investment portfolio (though these days, who knows what’s right, lol).

      One of the things that’s helped me, too, is that I’ve taken a number of major risks along the way. Some hit big, others bombed and I survived all. So it fortifies you to a certain extent and helps you realize most things are recoverable. Still, I’ve always said that one of the few things harder than being an entrepreneur is being the life-partner of an entrepreneur, especially when you don’t share the same risk orientation.

  21. I’ve actually never considered this topic before, so I thought this rather strange.

    Spot-on as always, really love the Kona Joe story from Career Renegade. It just makes everything feel much more realistic, no less urgent, but tempered as well.

    I think that’s what so many of “us” have an issue with: Our monster passion burning away inside while the minutes click off the work clock. Some days you wanna lose your shit and leap, but that doesn’t necessarily make it the best decision over the short term.

    For those of us working two or multiple gigs, there are magic days when somehow, magically, it all lines up. We’re able to use our passion for our day gig, and vice versa. This is the essence of what I’m developing with my “full-life integration” experiments.

    I love that you raise these questions for the up and comers. It’s hugely valuable for the community.

    The Fields. He ABIDES.


    • Jonathan Fields says:

      Hey KC – I’m much more like you, I just want to dive in and I’m confident I can make anything work. But I’ve also learned that while I’m often right, that’s not always the best way to get to the longer-term vision.

      Mad as it sometimes makes me, fact is your ability to self-regulate is a critical skill set for success.

  22. Jacki says:

    The company I work for is planning major cuts in staffing by this time next year. I am working part time there and part time on several of my own ventures. The planned workforce reduction has forced me to stop procrastinating on my own business. All earnings from my own business are being banked. My plan is to have two major debts paid off with the employee income before the big lay-off. Then I will only need half or less of my current ‘job’ income and will still be able to travel and enjoy ‘retirement.’
    Thank you for the blog post. My business is something I plan to do for the rest of my life because it improves so many lives and I enjoy it.

    • Jonathan Fields says:

      Love it, Jacki. Sounds like a solid plan and it’s great that you’re thinking ahead and acting upon your vision!

  23. Heather says:

    This is a great article and really relevant for me as I work with people in their late 20’s and early 30’s – coaching them in navigating personal and professional choices just like this. Jonathan, I am just like you. I just jump and go balls to the wall because I don’t have kids, and I own a home that the tenants are paying for. Rather than ratcheting up my living expenses when my business got going, we moved to Peru where the cost of living is 1/3rd of what we were paying back home. Now, in less than a year I’ve built a thriving business and run international retreats for new entrepreneurs. I’m a big believer that no time is the right time and you really just need to make sh*t happen. But I find that most of my 1×1 clients, none of whom have children or big financial obligations are really struggling with analysis paralysis and some of them don’t even have the confidence to BEGIN the passion project that their heart really wants. I’m going to have them read this so they can see the options through a more logical scope. I hope it inspires them. Thanks!

    • Jonathan Fields says:

      No doubt, even when you’re earlier in life with far less to lose, a lot of folks end up “fabricating” reasons not to act that feel as real as the weight of much bigger responsibilities that come later in life. The key is the create the ritual of forward movement, regardless of who you are and where you’re beginning.

  24. Kevin Riedel says:

    Such a timely post as I am waist deep in this situation right now. Time is what is holding be back. I’m not saying that I never have the time. Believe me, I find it. I wake up a couple hours early in the morning and I’ll stay up late at night to grab a couple hours. And I’ve basically eliminated television from my life. I just need more (time, not television!).

    I spend my 9-5 in a cube. When I head home, I’m a father to two young children. Once they’re in bed, I’m hustling. But when I look at a week of time that I put into the side hustle, I rarely get more than 12 hours a week. 12 hours! A lot of people work that in one day!

    At the end of the day, I realize that it’s forward motion and that’s better than no motion at all. But as the weeks turn into months and the months into years, human nature makes me impatient. The change I so desperately crave is coming slow. Thoughts of quitting the 9-5 to break through on my side hustle cloud my mind almost daily. In fact, just the other day, I convinced myself to get up and quit my day job. I stood up from my desk, ready to walk into my bosses office. As I did this, I saw a note on my wall that said “I love you daddy.” from my daughter. I slowly sat back down.

    As much as I want to lean into uncertainty, I have to remember what’s most important to me. I’ll keep hacking away hour by hour until can meet one of those three criteria. Thanks for the reality check, Jonathan.

    • Jonathan Fields says:

      Kevin – No doubt, it’s a tough challenge. Everything changes when you become a parent. Often it means the process gets more spread out, but the important thing is that you’re still engaged in the process.

      One interesting thing to explore if you want to create a big bump in momentum or even experiment to see if you’d really like it as much if it were full-time would be to take a side-hustle-cation. Take a few vacation days to spend working on the passion project full-time, and be very deliberate about setting them up so that you can get a ton done.

      And, remember, too, for many people, there is still a leap of faith that must be taken, because the entrepreneurial venture will never do what it needs to do or fully prove (or disprove) its viability until you go all-in.

      No easy answers here, but open conversation about the real-world impact of life-cycle is important.

  25. Erin Feldman says:

    I’m currently building on the side. For me, it’s yet another lesson in patience and in not listening to the voices inside my head that tell me I’m not working hard enough or that I should quit building. Working full-time while trying to build something is not for the faint of heart or the impatient.

  26. You’ll be able to quit your day job when you have a reliable minimum monthly income coming in from your side business.

    That’s essentially what I ended up doing. I started my consulting business on the side and grew it over time. After about 12 months, I realized that my time spent at my day job was getting in the way of how much I could earn consulting; at that point, I went part-time at my day job while I ramped up my business, and a couple months later, quit my day job completely. But one thing that helped was that my consulting income and workload was consistent and consistently growing.

    However, I didn’t start my consulting business thinking that it would eventually become my full-time gig. When I started consulting, I just liked having the extra money–which was wonderful. I started my consulting business in January 2007, and within about 15 months was able to phase out my day job. Since then, I’ve QUADRUPLED my former day-job salary, and I’m MUCH more secure being self-employed and having lots of clients than I ever was by having a single employer.

    There’s no way I’ll ever go back to a “real” job.

  27. Jeff Bronson says:

    Personally I’ve tried doing both, for many years since 2004. I worked dead end sales job after sales job, while building an eCommerce site on the side. Never having enough $ to put into inventory, to market, to have any savings, while changing jobs multiple times a year.

    Fast forward to 2012, while my eCommerce shop alone doesn’t provide a full income, I’m expanding it to other niches. My experience led me a professional position in the SEO/PPC industry, which is helping me become 100% debt free and have 2+ years of backup savings in the next 2 years.

    During this time I’m building 3 more ecommerce shops off my original, plus using my knowledge to help other shop owners via a consulting site I launched.

    It’s a different path than initially seen, but it’s finally starting to work out. The possibility of freelancing will always be there as well, making the eventual leap much easier.

    It’s a tough slog, and I’m running out of steam, taking a lot more time for enjoyment lately, since I’ve blown much of my 20’s and 30’s on this.

    I’m now 37 with no wife, kids or mortgage, so it’s not too late! 🙂

  28. […] fabulous article Leap and Pray or Build on the Side by Johnathan Fields brings up some really good points about this process I recommend it to anyone […]

  29. […] Fields – is a former lawyer turned serial entrepreneur. Pat Flynn – was laid off of his job as a senior drafter for an architecture firm and has been […]

  30. […] Fields (@jonathanfields) addresses a question that almost every entrepreneur faces at some point: Should I quit my day job and go all-in on my passion, or work it on the side? Fields considers the fact that the older you are (and the more responsibilities you have), the […]