The “Big Goal” Roadmap

stock-photo-28840778-east-coast-under-loupeAuthor’s Note: This Big Goal Roadmap has been updated! Please see the new and improved Big Goal Roadmap here.

The common rule is that a goal must be SMART (Specific, Measurable, Assignable, Realistic, and Time-Bound). Making a high-level plan to get there ensures I have covered those bases. The following is my big goal and a brief overview of how I plan to accomplish it. Below that will be periodic posts updating progress toward this goal as well as detailing interim, smaller goals.

Specific: Retire From My 9-5 Job

This is the idea behind this whole endeavor. I want to have the freedom to raise my kids, enjoy my wife, travel, work at my leisure, pursue other passions, and relax. I want to own my time. I want to do this without having any financial worries or experiencing a noticeable drop in lifestyle

Measurable: (Passive Income + Side Hustles) > Expenses

In the initial phase of retirement, I’m content with having to “hustle” for some income, but I want to fund the vast majority of my expenses with passive income and without tapping into investment principal.

Assignable: It’s All On Me, Baby

Although I do have a very supportive family.

Realistic: Yes

See Below for Strategy

Time-Bound: Baby 29’s First Day of School (Sep. 3rd, 2019)

This goal date is about five years from day zero; I’ll be 34 years old. To do this, I’ll have to overcome a rather significant problem.

Here’s the problem:

Current Situation(End of 2014)
Current Expenses$9,000
Current Passive Income$300
Current Side Hustles$0
Surplus (Deficit)($8,700)


Near-Term Strategy (Jan-Jun 2015):

Decrease Monthly Expenses (see financial reports here) from ~$9,000/mo to a far more reasonable $5,000/mo.

  1. Cars: Sell our two luxury vehicles (a two-seater Corvette Convertible and a Mercedes Benz) and purchase a family-friendly, economical vehicle. The associated insurance costs, personal property taxes, gas, maintenance, and car payments would save (conservatively) about $800/mo.
  2. Housing: Get a new job and move back to our permanent home in Virginia with an equal or higher salary than what I’m getting in NYC. The housing savings would amount to about $2,800/mo. Proper management services will facilitate this process.
  3. Food/Other: The cost-of-living premium for food, dining, and household goods in NYC is, wet finger in the air, about 40%. I believe moving will save us $300/mo on these items.
  4. Phone: Consolidating under a low-cost carrier should save us $100/mo.

Increase Passive Income from $300/mo to $800/mo

  1. Dividend Growth Investing: Roll my idle 401(k) balance to a self-managed Traditional IRA focused on dividend growth investing. Immediately increasing my dividend income from $250/mo to $750/mo.
  2. Interest: Continue contributing to life-insured annuity, which currently yields $50/mo.

Start Side Hustlin’ from $0/mo to $100/mo

  1. Writing: Do what I like to be best, talk about stocks! Start writing on ~1 Article/mo.

These efforts should get me to here…

Mid-2015 Situation 
Monthly Expenses$5,000
Monthly Passive Income$800
Monthly Side Hustle$100
Surplus (Deficit)($4,100)

Mid-Term Strategy (June 2015 – June 2019):

Decrease Monthly Expenses from $5,000/mo to $4,900/mo.

  1. Other: Optimize the use of rewards credit cards/gift cards to further eliminate $100/mo from categories like travel, utilities, and food and household costs. Dropping just $100 in expenses over the course of four years seems almost too easy of a goal. However, I’m gaming on adding a few children to the mix over this time, so that will likely offset a lot of my expense optimizing effort. I don’t really worry too much about inflation.

Increase Passive Income from $800/mo to $2200/mo

  1. Dividend Growth Investing: Continue maximum-funding our IRAs and 401(k), and rely upon solid, blue-chip dividends. Between contributions, dividend reinvestment plans, and probable corporate dividend increases, I plan to increase dividend income at compound annual growth rate of 25% per year, from $750/mo to $1,800/mo.
  2. Interest: Continue contributing to life-insured annuity, increasing interest income by 15% per year, from $50/mo to about$100/mo.
  3. Rental Income: Acquire 2-3 rental units yielding a average monthly net income of $400/mo. This can (and probably will) include us renting out our basement either full time or part time (like AirBnB).

 Keep Side Hustlin’ from $100/mo to $500/mo.

  1. Writing: Do what I like to be best, talk about stocks! Increase writing on to ~4 Articles/mo.
  2. Blog: Not expecting a cash cow or anything, but it’d be great if I could monetize the blog to the extent that it pays for itself.

These efforts should get me to here…

Mid-2019 Situation (Proj.) 
Monthly Expenses$4,900
Monthly Passive Income$2,200
Monthly Side Hustle$500
Surplus (Deficit)($2,200)

Long-Term Strategy (Mid-2019 – Retirement…)

Decrease Monthly Expenses from $4,900/mo to $3,200/mo.

  1. Housing: Refinance and rent primary home, decreasing mortgage payment from $2,800/mo to $2,200/mo (thereby making a $2,500/mo tenant cash-flow positive). Upon entry into retirement, move to cost-friendly locale, taking out a mortgage and total housing costs not-to-exceed $1,100/mo. Ultimately, decreasing housing costs from $2,800/mo to $1,100/mo. Once retired, there shouldn’t be much need to stay in the high-cost DC suburbs of Northern VA.
    1. Back-up option: Rather than refi-rent-and-move. Simply sell our current primary home, take that equity and buy a similar home with cash in a low-cost locale. This would decrease our expenses another $900/mo or so, but would obviously remove the extra rental income shown below. We’ll explore this based on how things turn out.

Increase Passive Income from $2,200/mo to $3,400/mo

  1. Dividend Growth Investing: Continue maximum funding our IRAs and 401(k), and rely upon solid, blue-chip dividends. As retirement nears, fold in growth-oriented Roth IRA and 401(k) into the dividend portfolio $1,800/mo to $2,600/mo.
  2. Interest: Continue contributing to life-insured annuity, increasing interest income by 10% per year, from $100/mo. No real material change.
  3. Rental Income: Add our current primary home to our slate of rental units (see 1.a directly above). Along with small increases via inflation, increasing rental income from $400/mo to $700/mo.

 Keep Side Hustlin’ from $500/mo to $800/mo.

  1. Writing: Do what I like to do best, talk about stocks! Increase writing on to ~8 Articles/mo.
  2. Blog: Not expecting a cash cow or anything, but it’d be great if I could monetize the blog to the extent that it pays for itself, potentially a bit more.
  3. Part-Time Work: This would hopefully be unnecessary, but my wife and I are still fully capable and healthy adults with pretty good skill sets. Should any of the above fall through (dividend cuts, bad tenant, unexpected large expense), we can always resort to a little part-time work. $0/mo.
Retirement Situation (Proj.) 
Monthly Expenses$3,200
Monthly Passive Income$3,400
Monthly Side Hustle$800
Surplus (Deficit)$1,000

Is this possible? I’d say it’s certainly possible... but, it’s also certainly aggressive—which is fine with me. I’ll try to post updates at least quarterly with progress toward this goal, but the monthly financial reports should touch on it consistently.

There is one follow-on goal. Once retired, I’d like to continue to decrease any reliance on “side hustles.” Not that side hustles are any less reliable than regular work (what is regular work other than a side hustle that takes a ton of time?), but I’d like to continually gain more freedom and ownership over my time. My retirementality is that working in some respect is always going to be the case—but I want to freedom to not have to work.

Tell me, am I insane?


    • Daniel,
      I’m so happy to hear that. I wish you all the luck in your journey. The numbers don’t lie. The best part–even if I’m off by a little bit, that’s still a rousing success.

      Thank you for reading and commenting.

  1. Your idea for rental property is right on. We have made about one million dollars in real estate over the past thirty years. Not a penny of it from the stock market. We had twenty one rentals at one. Sold the income property last year and am now in to the stock market. We found an area in the rental market that wasn’t being met – small one bed room apartments that were ideal for one or two people. We built two four unit and one five unit buildings. Over the years we had several house and built a three bed room duplex. Found out three bed room rentals were far more trouble than one bed room units. Getting started you have to do three things – have new buildings which are easy to maintain – be able to do all the work your self, cleaning painting and repairs – live close to your rentals. Real estate and rentals are better than the stock market because you operate with other people’s money. Good luck. You have many years to make money and enjoy your family.

    • Thanks Rick, tremendous insight from an obvious veteran landlord. That’s a rather robust real estate portfolio you’ve built up–you’re like a junior Donald Trump. I’d love to get just 3 or 4 units (plus our eventual lease of our primary home), en route to generating $1k is passive income–net of management fees.

      Very impressive that you could do all the management yourself for that broad of a portfolio.

      Thank you for commenting and for reading.

    • J. Money,
      First, I’m a big fan. Thanks for all you do at Rockstar and your other sites. I appreciate you stopping by and commenting. To point, seeing all the old financial baggage fall away is super motivating–just wait for this month’s expense report.


  2. Love your post! Question for you, how are you going to take money out of your 401k and IRA before 59 and a half? 99% of all my investments are 401k and Roth IRA and I thought I couldn’t access them and would have to start some taxable accounts so I can retire in 10 years. (Thats my goal!) Thanks for your help!

    • Definitely a valid question. I’ll roll my about $30k/year from my traditional IRA to a Roth starting my first year of retirement. I’ll have to pay taxes on the rollover, but my deductions will nullify almost the whole tax bill. After five years sitting in a Roth, I’ll be able to withdraw the amount without tax or penalty. I’ll have enough in my current Roth and Taxable brokerage to get me through those first few years pretty safely.

  3. Have you taken into account additional spending over time with the child (or potential children)? I’d have to imagine spending will go up for the ‘kids’ bucket, therefore offsetting some of your monthly expenses reduction?

    • Hi Ryan,
      Spending will definitely go up, I’m sort of counting on it. However, despite the many reports of insane child costs, we’ve found that children (so far) are a far less burdensome cost that purported in the media. I did write one post on it, showing how our first baby has actually made us money so far. If we had a second child right now, it’d be super profitable, given the tax benefits and the fact that we already have most everything we need for the first few years of life (except diapers and wipes).

      Children are generally as expensive as you want them to be, we’ve found. We spend a lot of time playing, walking around the neighborhood, watching some Netflix, and other non-materialistic things. We try to avoid needless waste. Check out that post for more in-depth analysis.


  4. Awesome blog Mr. 29. All comes down to minimizing expenses and looking for side/passive income. I am a few years elder than you yet 100k behind, and worse still, living in expensive norcal. I’ve started a couple of side-business ( is managed by my wife and I ‘ve outsourced some of the work to Africa (80% cheaper). Furthermore, I am looking at my first 4-plex that will bring $700 in positive cash-flow. My biggest mistake in the last 4 years was to take a big gamble on risky 3x ETFs but I’m more conservative now. Hopefully I can turn this ship around.

    • Nash,
      I hear you on those 3x ETFs, those are some dangerous weapons that can quickly turn around on you. I’m never touching them again. I talk about how I was killed with those in this post. I don’t envy you living in NorCal, I hate high costs of living–it just seems wrong. Luckily (or hopefully), your income is tracking those costs and you’re able to start piling up a nice cash pile, then you can use geographic arbitrage after retirement.

      That 4-plex might be enough to retire on in a few years. I wish I had one.


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