Fork In The Road

A Fork In The Road – Retire Early, Stay On Career Path Or Try Something New?

in Financial Planning by

“Speed has never killed anyone. Suddenly stopping, that’s what gets you.” – Jeremy Clarkson

I’ve been successfully racing around the career track for 30 plus years. I’ve written screenplays in Hollywood, have been an advertising copywriter, and have held marketing leadership roles with Silicon Valley start-ups and Fortune 500 companies. In March 2014, my 11-year career at an online broker came to an abrupt stop when my position and department were eliminated. It didn’t kill me, but it did get my attention.

This sudden stop also gave me the opportunity to assess where I was, what my wife and I wanted for our future, and how (or if) we could get there.

So what kind of shape was I in?

I was about to turn 55 and unsure about what to do next – continue on the same career trajectory, try something new, retire? All options were on the table.

My wife had retired about 3 years earlier, so for at least the short term we would have no money coming in.

I was concerned and maybe a little worried. Fortunately, my wife was there to help me out. The first thing she suggested was I take my time. We had money in the bank and my severance package would serve as a nice cushion.

So I took the time to look at my life… my career ambitions, my health, and our retirement goals.   I did two key things: I scheduled a physical and sat down with my wife to review our finances.

The Physical Check Up:

The news was tough. I was out of shape, had to lose weight (even more than I thought), change my diet, and start exercising. The doctor set a weight loss target that really threw me. But he gave me a year to reach that goal.   What the doctor didn’t give me was a way to reach it.   I went online to find a solution that would work for me.

One mantra I especially like is, “what we measure, we can manage.” So, I selected a comprehensive food and fitness app that allowed me to measure my progress. I can set my goals (lose 2.5 pounds per week), track my exercise in calories burned, and track each element of all my meals by calorie. I was assigned a calorie goal for each day that I must keep to meet my weight goal.

I enter data and track my progress on a daily basis, but still keep an eye on the big picture. . And with big goals that seem too large the ability to break it down and focus on something as incremental as a day, or even a meal. The app is synced to my laptop, tablet and iPhone. The app is synced across all of my devices, which means it’s too convenient to ignore.

The Financial Checkup:

Wow. Eighteen years together and our financial accounts were all over the place.   Multiple checking accounts, various credit cards, my 401K, my wife’s 401K, two separate brokerage accounts, a mortgage, a CD we bought when we sold some property, and oh yeah, an IRA my wife opened 30 years ago.

Some of these we could track online, others we couldn’t. Almost all were at different institutions.   (We also had telephone, cell phone, Internet, and cable TV contracts that were out of control, but that is a discussion for another day.)

With so much clutter, and no single, consistent picture of our portfolio and cash flow, how could we make any projections for our future? We didn’t even know what was going on in our present.

With a full-time job, I had a paycheck deposited every two weeks, my 401K was funded at the same time (and matched by my employer), cash flow was consistent, and it was easy to not pay attention. But now, we realized we needed to see all our finances in one place so we could make intelligent decisions going forward.

Again, I went online to find a solution.

I selected Personal Capital. With Personal Capital I was able to see everything I had, all in one place – a clear picture of our net worth, including our home value. I could review cash flow, analyze investments, understand what fees we were paying and how assets were allocated.   I downloaded Personal Capital to my iPhone, my tablet, and to my laptop.

The next step was painful. Not because of Personal Capital systems and ease (that was anything BUT painful), but because of the light it shined on some pretty dark corners.

I had been “managing” my 401(k) on my own… searching for wins, not checking on fees and not able to see if I had overlapping investments. I ran my 401K through the 401K and Mutual Fund Analyzers at Personal Capital.

The read out was brutal.   I had what I can only describe as the most unbalanced portfolio anyone had ever seen – certainly not one appropriate for someone who planned to retire in just a few years.   And based on the 401K analyzer, the fees I was paying on the mutual funds in my account would cost me more than 4 years or more of my retirement… the fees were costing me more than money, they were costing me time.

Whatever investment strategy I might have had at one time was long since abandoned… my 401K portfolio was a random series of mutual funds.   I’d like to think this happens to a lot of people. We set our investments and then forget them…or we go in and tinker with them based on today’s market conditions – forgetting or never having had an investment strategy.

Fortunately amateur hour came to an end.

Which Way To Go?

As I started to get the rest of my life in order, I had to think about what was next in my career – and how we were going to finance it. If I was going to work, I really wanted it to be a job where I could continue to be creative, but with more flexibility in terms of time commitment.   I knew we didn’t need as much income as before, but I wasn’t sure what that meant.

  • I considered retirement. We could pay off our mortgage (so we would have no large financial commitments) and still maintain a decent lifestyle. We would have to carefully manage our assets. It might mean reducing some principal – finding a balance between short-term needs vs. dividend income over time. We would have to be careful about expenses like travel, entertainment, and dining out.
  • I could go back to work fulltime.   I leveraged my network and interviewed with companies about similar positions to the one I had just left or even higher up in their organizations. Financially, these jobs would be great. Egotistically, I would have loved to have a high-paying, high title job. I could continue to fund my retirement accounts at the highest rates and get all the benefits of working full time – health coverage, bonuses, paid time off. But each time I interviewed I felt like I had lost another piece of my soul – I felt like I was getting back on the same fast track I had just gotten off.
  • I could become a marketing consultant. But what did that mean? And who would hire me?   The benefits would be freedom to pick and choose my assignments. The downside would be that there could be long periods of time without any work. Benefits – like health insurance, retirement programs – would be solely my obligation. But I wouldn’t have to worry about the commute!

In the end, the decision was easy.

A friend from a previous job asked me if I could help out on some marketing assignments.   I became a consultant, and I couldn’t be happier.

My income may be lower than when I was working fulltime for the online broker (it could also be larger, as I am able to add clients), but not by much.   I work from home, so my expenses are relatively low.   I set my own hours and work on every project I get (hahaha, I don’t know many consultants starting out who picks and chooses assignments), and have the freedom to pay attention to things other than work.

A Change In Attitude

With this change in career trajectory, my wife and I have also changed our investing outlook and strategy.   Before this, we were looking at growth with a high-risk tolerance – after all, the cash was flowing in, and retirement was a distance away.

Now we won’t have the opportunity to contribute as much to retirement plans (and it won’t be matched).

I’ve taken greater control of my 401K by rolling it over – a simple process. I’m moved away from mutual funds and their higher fees, and am now invested in a more balanced portfolio of individual stocks and ETFs.

While we couldn’t continue to be super-aggressive in investing, in some ways we are more aggressive about our portfolio now because we understand how it defines our retirement. Based on getting a complete picture of where we stand, I know now that I could be completely retired in 7 years or sooner.

After years in the professional world, I’m competitive, and my instinct is to BEAT the market. It’s something I have to remember when I look at my Personal Capital dashboard. Our risk profile has changed. Our goal is to grow and, more importantly, to maintain the bulk of our portfolio… wild swings in the shorter period before our retirement could be tough to make up.

Measuring Progress

So it has been about nine months since my old career – my old life in fact – ended and the new one began.   I continue to measure and manage both my finances and my fitness.

On the fitness side, I have lost all the weight the doctor recommended. I did this within six months, half the time suggested, and have kept it off. At Thanksgiving I ran our local “Turkey Trot” 5-miler in an hour… the first time I have run more than a mile in 40 years.   I continue to track my calories and almost daily workouts on the app I downloaded in March. I’ve never been in better shape.

I think the same can be said financially. When the Personal Capital Forecast tool was launched, I used it to check our progress against our retirement goals. We are tracking in the right direction – but I check in almost daily.   I like to run different scenarios based on retirement date and the amount we might have saved at that date.

I use Personal Capital to track the spending in our checking and savings accounts, credit cards, our mortgage balance and investments daily.   Because I can see what I have and what I am spending I am making better financial decisions. Regularly scheduled bills and expenses no longer surprise me.

What we measure, we can manage. But it might be the things we can’t measure — like feeling healthy and financially confident– that are the most important things. For me, an abrupt stop allowed me to begin. But you don’t need to stop everything to reset… just download and link using the free Personal Capital software so that you can begin today.

Photo credit: Eric Vondy Flickr Creative Commons

Join Personal Capital To Manage Your Finances Better

The following two tabs change content below.
David Douglass

David Douglass

David Douglass is an award-winning marketing professional. He has held marketing leadership positions with Silicon Valley start-ups, Fortune 500 companies, and a leading online broker. He started his career as a screenwriter in Hollywood before working as an ad agency copywriter. David is a graduate of Wesleyan University.


  1. Roy Mullins

    well written.

  2. David Bruggeman

    Very engaging read, the closer to retirement the easier it is to make that choice.

  3. Javaid Bashir

    Excellent article. Very well written. Great ideas for the retiring persons. Do not have to worry finding a Job. Almost everyone can become a consultant in some field. And can work from home. and save extra expense.
    Do not have to worry for 9 to 5 schedule, or reaching on time to the office. Could make own hours of work in a convenient fashion. Thanks buddy.

  4. bob

    Is this a real story or just a money making plug for the various mentioned apps? When life gives you lemons, sell them for retirement income.

    • David Douglass

      David Douglass

      Bob — this is a real story. I am a marketing consultant, my wife is retired, and we have linked our accounts at Personal Capital.

  5. Melvin Veney

    This is wonderful to hear. It couldn’t have come at a better time in my life!

  6. Jo

    What if you’re NOT a “former Marketing executive” who “worked at Silicon Valley firms & Hollywood”. What if you’re just a normal person who made normal wages – where do you go to find out that information? Everything written today about retirement always talks about “professionals” and “executives” – when they’re probably the LAST people who need help to retire (they can afford to hire someone) – and almost sounds like bragging because of all the “portfolios,” savings accounts,, multiple 401-ks and mutual funds. What if you only have your 401-K, your IRA, small pension and some savings? Does anyone out there care about regular people?

    • Suzan

      I TOTALLY AGREE……….we can get lost in the shuffle and the majority of our voices are NOT heard…….the everyday people who have contributed to the “poor” and social services do not even qualify, and the govt finds every excuse to reduce our Soc Security and stuff to give it to those who have never contributed and may not even been citizens! Something wrong with this picture.

    • Mr CB


      I would recommend Dave Ramsey. He’s got a lot of good information that applies whether you make $20k or $20M/yr. The info is pretty basic but it has been helpful to my wife and I.

      Good Luck,
      Mr CB

    • RSoames

      None of this is relevant to most people who are 55 and who don’t have the privilege of navel gazing after being laid off. Great advice for the already wealthy, though.

    • kim

      Jo, I am just a regular person. I just made the choice to finally stop working. A long time job which I have disliked for many years. I left it at age 59 this past year. I am able to be debt free and have enough in investments (my own money) not given to me by a company and still be fine until social security kicks in and will be just another little bit to make life even nicer than it is now. It takes long term planning and lots of discipline on spending habits. Good luck.

  7. Don

    You have a link to Personal Capital and I see that this is sponsored by Personal Capital but you also mention a weight loss app but do not share a link to that app. Which app do you use for fitness?

    • David Douglass

      David Douglass

      I use

      • Ed

        I have used Livestrong as well. If you stick with the program, it really does work. I was 225 (male; age 59; 5’9″) and lost 50 pounds in about 4 months of focus – exercise (3 to 5 mile daily walks only) and diet. Highly recommend the Livestrong site and app. If you don’t want the extra bells and whistles (and that’s all they are), then its free.

    • JK

      I have no idea which fitness app David Douglass uses but I use MyFitnessPal. It not only tracks your calories & weight but also tracks carbs, protein & fats. You can easily access sugar contents too, which is the most important factor in health & weight loss/maintenance.

  8. Lisa Stansbury

    Hi David, thank you for sharing your personal story. Sometimes it’s hard to put it out there, I know. I hit the same wall myself just last week, and have spent my last two weeks just cleaning up the financial picture.
    But I also do understand Jo’s question. A lot of people over at Early Retirement and Get Rich Slowly websites are helping out those like me and Jo who never had a large corporate salary to begin with. Career changing/early retirement/downshifting…whatever you want to call it, is possible, even for moderate earners. I can vouch for that and am thrilled to have this opportunity!

  9. Ray

    David, I am in the same boat same age but my wife is still working but threatening to quit every day but because of insurance and my son in school she has to work for a Little longer but I have been self employed for several years just building some equity in real state but otherwise IT background and multiple accounts is the same scenario and it is funny I have done the same for my wife 401k last week just moving to stock etfs and one mutual fund at fidelity.
    Last night I finally figured out what Benjamin Graham said many years ago buy stuff that is cheap and warren said when blood is in the street…if I had the foresight or taken a breather I would have bought builders and spg, vernado or any of those property stocks I could have bought when I was losing my shirt in real state…now I could have retired with just 200k in 11 year time span …so key is buy what nobody wants…and stop chasing the hot sectors and hot stocks…so simple an idea but I didn’t follow it, it took me 25 years to figure it out…Thanks for all those great ideas…u created a recipe for me.

  10. Dre

    Quite nice. I virtually eliminated added sugar, and processed foods from my diet. For some strange and great reason (at the same time, yes) I really like vegetables. Beginning to look like the skinny kid I was at 17 but only now I eat healthier by choice. Still youthfully active and appreciating the size 34 waist as opposed to the 38. Jelly belly gone to almost flat. And, at 49, I just began law school. Teaching science courses on the side and spending lots of time in the ocean. Talk about ccccrazy but I’m lovin’ it. Retire? LOL.

  11. henry

    There is something very inspiring about this article, thanks for writing about your experience. Your ‘can do’ attitude is contagious!

  12. Toad Von Fuddge

    Ahoy Mateys!

    I’m quittin’ my job today. Gonna drink beer and have fun.


  13. Cat

    Get ready for a lot of disappointment for most who must or for those who decide to make a career change in their 50’s. I’m a divorced woman with no children. It was at the height of the economic downturn when I got laid off and then spent two years wasting my savings looking for a replacement job. I worked for 23 years in an industry that was one considered high tech. But young people college were very computer savvy and for the most part were able to do their own work. My department’s services were required less and less. in the 1990s a standard department at a large firm hired up to 12 employees like me; 20 years later there were two or three of us at most in a department. The other thing I had to accept is that in spite of it’s being against the law, age discrimination and alive and well. I finally had someone (who worked in the employment industry) admit to me that no one would hire the older worker if a younger worker with the same skills were available. The employer was also able to start the younger worker at a lower salary because the generation or two behind me is desperate for work. I’m now earning 1/4 of what I earned for 23 years and life is suddenly dark with worries about making the rent from month to month. I pray my old car remains roadworthy for a few more years. I’m so worried about my finances I’m considering taking early retirement at 62 just to be marginally safer financially. There were also some financial setbacks (i.e., disasters) during that period that contributed to my financial situation . Without family or friends in any position to help me, my savings and 401k are both exhausted of funds. Never did I consider I’d be in this position toward the end of my work life. Hard lessons have been learned . I’m thankful I’m better off than I was two years ago when I was one-month away from homelessness and reading up on how to survive the streets if that were to become a reality.

    • Pat

      Cat, I hear you. I have been in the graphic arts business for 30+ years. 11 years ago I was laid off from my full time job. Not able to find another full time job (most design firms want younger/less experienced people), I started freelancing. That worked out great for awhile, but at age 57 I find that most of my freelance clients have either gone out of business or slowed down significantly. My husband is still working but does not have a high salary. I have not been able to fine even a minimum-wage job. Luckily I do have some savings (that I was going to use for retirement), but that will be pretty much used up by the time I reach 62. I have to purchase my own health insurance which has skyrocketed. I think a lot of folks our age are experiencing the same thing. Makes it pretty difficult to “plan” for retirement!

      • Cat

        I think we’re in a very large boat, Pat. I make a little more than minimum wage as a caregiver. I used to make in the low 80k range. I live in Northern California with the one of the highest costs of living. Rent for a one bedroom apartment averages $1500 month. I can’t afford to move, well, because I can’t afford to move. I have no vacation or sick time and no medical insurance, which I am unable to afford even under Obamacare. I make so little money I am exempt from paying the government fine for not having medical insurance. I live each day worrying about the next. I don’t feel sorry for myself, I am simply stating it is what it is. I’m grateful I’m in a better place than I was two years ago but it is still far from where I expected to be. That’s why the article I responded to kind of ticked me off. So many of us do not have the luxury to plan anything and only hope and pray that we can maintain our status quo.

        I sincerely hope that things get better for you.

        • Pat

          Yes, I agree – articles like this are written by people who don’t have a clue what it’s really like out there. I think there is a huge problem that isn’t being reported in mainstream media. I’ve started a pet sitting business but it doesn’t begin to cover my basic expenses. I’m trying to live one day at a time. I hope things get better for you, too! (For all of us!)

    • Thomas Cappiello

      A much more realistic expose’. I was there once. Jobless, living with my mom (how embarrassing) and depressed. But persistence in the end wins. Never give up. I didn’t and got out of it, but can’t say that I’m way ahead of everybody, but doing ok. Tom Brown’s Urban Survival was a great read!

      • Cat

        Thank you, Thomas. I have found work in caregiving — the only profession that would hire me at my age. The pay is terrible and the work is hard and often depressing but I am able to pay my rent and buy the food I want to eat and I am very grateful for this. Glad you are doing well. Happy New Year!

  14. Tom

    Felt like I was reading an article about myself. Well written and informative. Thanks,

  15. Victor Padilla

    Sadly, only two reply’s from David Douglass. Sorry!!! sounds like a sales pitch for personal capital.

    • Kevin

      Oh course it is a pitch for “Personal Capital”. The difference is that it uses an example to explain what services they do. In the end, use them if you think it will benefit you enough to justify the costs. I have read several articles at this website. some are quite good. Others, like this one, are a mixed bag. Let me break this article down, as I see it:
      -It’s easy to get on a path of investing for Retirement and then never take stock of how you are doing. This real example shows how it took a career crisis to make the author do this important step.
      – It takes time to dramatically change your investments or your health. So you need to look at these things at least a few years prior to when you retire.
      -“Personal Capital” is a company that can help you analyze your investments, and they’d very much like our business.
      Full disclosure: I have never been a customer of “Personal Capital”. And I don’t see that changing in the future. I do, however, read investing advice from many sources; including this website.

    • Thomas Cappiello

      a.k. infomercial

  16. Jim

    The promos on-line are pretty much the same script over and over. A guy making a zillion dollars a year is playing with the idea of leaving his job and becoming a shepherd. Can he “survive” on his dividend income only. Not withstanding his wife is retired from her high paying job and has a few dozen retirement accounts. The biggest issue is, “where do we hide the money?” This is symptomatic of the short shrift “our” legislators give to what was once referred to as the middle class. Unless a person is fortunate enough to be enormously well invested, there really is no retirement, per se. Good positions are few and far between thusly the employer holds the upper hand regarding wages and working conditions. If you don’t like it, leave. I could go on. These articles are patently disingenuous to the overwhelming majority of us who will be working until we drop in our traces. Nice to see that folks have written to express the truth of real life.

    • Anonymous

      Well said. We will be working until we drop; that is if we are lucky enough to FIND work . . .

    • Cat

      Thank you….

  17. Mac

    interesting story,,,but here I will have go agree with Jo,sounds like a bunch of bull,you talk about all your finances-how much you have………its time for you to realize ,most people do not have your wealth….thousands of us normal people struggle week to week to maintain a roof over us,so many of us have been stepped on by the corporate world,we work at fast food barely making a wage….now I have been disabled ,no future in site,the monies tat I get are extremely limited…..lets us not forget the homeless ppl. that the govt. .and corparations have put out and left to due with what they can scrounge up on a daily basis…the govt. and society don’t care about the little ppl. only bigwheels and the rich..

    • Anonymous


      The whinnypants brigade is out in force. Have you ever stopped, just for a moment, to realize that YOU are the reason that your life is the way it is?

      • Anonymous

        Let them eat cake (?)
        You have to have money to make money. If you don’t make enough to “invest” you are pretty much screwed.

  18. expatinasia

    Just another advertainment…an ad for Personal Capital, a waste of time.

  19. Tom

    This “personal capital” software sounds needlessly complicating. complexity does not lead to good results; “keep it simple stupid” as they say! rules to live by are to adhere to a budget, save constantly, plan for the future, lower your fixed costs, etc. and if you do have money and savings and investments all over the place, by all means consolidate them into one place. and just run a simple spreadsheet to do a budget with. yeah it is true that incomes are going down -fast- and that the middle class is disappearing because the government and business has decided that we don’t need one. at this point, its all a race to the bottom. so deleverage, pay off loans, live with a much lower standard of living, etc. social security and medicare isn’t bad when it comes at 62 and 65, respectively. finally, think about how you’re living and if it could be done for less. Sorry about the cold bath of water that life has become, but we really all had it coming as we just had it too good for too long in an otherwise impoverished world. Time to come back down to earth for most of us. so get over it. Its all gone. Sorry.

  20. Julio Gonzalez Jr

    I have some better feelings about the war against ISIS.There are new symptons that the Afghan Army with consultants from the US military in Afghanistan are turning this around.What is really a pity is this earthquake that hit Afghanistan and Pakistan.The Pope Francisco have also declared that peace negotiations must be the number one priority. it seems like ISIS will never be ready to seat with their rivals for peace negotiations.No rush. We need to get a strong control of those territories retaken by the Afghan Army and using new strategies and tactics to get the ISIS terrorist group off balance. Sincerely Julio Gonzalez Jr


Leave a Reply

Your email address will not be published.

Disclaimer. This Website may contain links to third-party websites. These links are provided solely as a convenience to you and does not imply an affiliation, sponsorship, endorsement, approval, investigation, verification, or monitoring by PCAC of the contents on such third-party websites. Please be advised that PCAC is not responsible for the content of any website owned by a third party.