Use the Holidays to Your Investing Advantage

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There are numerous ways I could tell you to use the holiday time to benefit your investing career.

I could list out some number of specific things you could do, I could tell you to take advantage of other investors not being out shopping for properties or generating leads because they are otherwise occupied with holiday hoopla, or I could tell you to take advantage of seeing all of your family and friends over the holidays and try to poke them on their investing desires and see if you can’t strike up a killer partnership or funding deal with them.

But, I’m not going to. I’m thinking more along the lines of… tell you something you can do over a relaxing night with some eggnog (alcoholic or otherwise), a glass (or 5) of wine, while you rest, and while you kick back and do nothing.

Reflect and brainstorm.

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Are you where you’d hoped you’d be with your investing at this point in the year? Whether you are where you wanted to be or not, this is a time to congratulate yourself. This is not a time to get down on yourself for not hitting your goals, if that is the case, or for anything you didn’t do quite as you’d hoped. No matter how much you accomplished, or didn’t accomplish, you need to focus on what you did right.

For everything you did or didn’t do this year towards your investing career, think about the following things in relation to each:

  • Congratulate yourself! Even if you didn’t do something to the level you maybe wanted to, you at least started it. That’s worth rewarding yourself! That’s way more than a lot of people do. If you didn’t start that something, that is okay too. Congratulate yourself for thinking of it in the first place and putting in your plan. Trust me, there is always something you can congratulate yourself for and every little “win” matters.
  • Do it differently? Look at the things you did. Go through the process in your head and see if there are any ways you could have done it that would have gained you more, made it easier or more efficient, or something else you could have done in conjunction to increase the results. I didn’t label this one “learn from it” because everyone says that and I feel like “learn from it” has a negative connotation to it by suggesting you did something wrong. You never did anything wrong, no matter what you did (or didn’t do). There are just ways to potentially have done it better. So look at it from that angle, the positive angle, instead. Consider what you did a “win” and then think of how you could make it an even bigger win.
  • Things you didn’t think of? Maybe there is something you never even thought of doing this year. What is something you didn’t think of until now that you could have done this year? Even if it sounds crazy, that’s okay. Don’t rule anything out right away.
  • Were you scared?  Was anything you didn’t end up doing because you were scared or nervous about doing it? Or was there seemingly no way to do what it was you wanted to do, regardless of emotions?


Once you’ve reflected on everything you did (or didn’t do) this year, now it’s time to let your creative juices flow. This is the fun part, so be sure to have fun with it. You may not even need to think directly about the things you reflected on above, but as long as those things are in your subconscious, you will be able to start thinking about next year and what you want to do in that year. But get creative with it! I’ve learned in this business that it is never about “if” you can do something, it is about “how” to do something. Anything you want to do, no matter how crazy it seems or no matter how many people tell you to stop trying, everything is doable somehow. Some harder than others (by a big margin), but don’t assume anything is impossible.

Let’s set this up like a meditation. A hypnosis of sorts.

  • Forget reality. Forget anything you’ve ever been told about what can and can’t be done. Forget about anything anyone has told you that you should do (or shouldn’t do). Clear the slate.
  • Picture your dreams. What could you do this year that would make you feel awesome and accomplished? What goal do you want to achieve? Maybe it’s not even a set number or monetary goal, maybe it’s just something like “I want to flip houses all year, as many as I can” or “I just want to flip a house” or “I just want to buy a rental property”. Anything you want, picture what would really make you smile.
  • Use your reflection. Does anything you reflected on relate to what you want do to next year? If so, use your experience from this year to think of how to smartly do it better next year. Use your experience to be even more creative. If you didn’t do anything this year directly related to what you want to do next year, think of how you can use your general life experience to help you next year (i.e. resisting fear of failure, finding resources, etc.).
  • Come up with a general plan. Although I should label this one more accurately, “come up with a starting point”, I say plan instead though because you do need to know your bigger picture idea before you can come up with your starting point, but then come up with a starting point. I’m usually against written plans, especially official business plans, because there are so many new paths that will open up to you once you get started, you just never know which direction you might take. But written plans can’t hurt either. It really depends on what your goal is. If it’s to flip 15 properties or buy 10 rental properties, a written plan of how you are going to finance those and when you are going to finish or buy each property is certainly warranted.
  • Write down your starting point. Writing it down just makes it more official in your subconscious and oftentimes takes some of the fear out.

This process is, and should be, really fun. If it’s not fun, you are either 1) in the wrong line of investing or 2) way over-thinking it.  I said it half-joking about the wine or alcoholic eggnog, but this process should be so much fun, and therefore easy, it should only get more creative as the holiday fun continues. Notice I didn’t number any of the things to do either. It shouldn’t be looked at as a linear step-by-step thing. It is all one big picture. Picture it all together.

Start with the Win

My big win for this year isn’t directly investment-related, as my personal investing was on hold this year, but I did successfully survive my first year of starting a real estate investment business. That’s a huge win! So many hopeful entrepreneurs don’t even survive the first six months, much less a whole year. And trust me, now I know exactly why so many people don’t survive starting a business (it’s hard!).

What was your biggest WIN this year? How will you use it towards next year?

Photo Credit: jmtimages via Compfight cc

About Author

Ali Boone

Ali Boone is a lifestyle entrepreneur, business consultant, and real estate investor. Ali left her corporate job as an Aerospace Engineer to follow her passion for being her own boss and creating true lifestyle design. She did this through real estate investing, using primarily creative financing to purchase five properties in her first 18 months of investing. Ali’s real estate portfolio started with pre-construction investments in Nicaragua and then moved towards turnkey rental properties in various markets throughout the U.S. With this success, she went on to create her company Hipster Investments, which focuses on turnkey rental properties and offers hands-on support for new investors and those going through the investing process. She’s written nearly 200 articles for BiggerPockets and has been featured in Fox Business, The Motley Fool, and Personal Real Estate Investor Magazine. She still owns her first turnkey rental properties and is a co-owner and the landlord of property local to her in Venice Beach.


  1. This is good advice. The end of the year is a time to evaluate. I’ll tell you that this site is probably intimidating to many new investors – whether flippers or buy and hold. Everyone who visits here should know that it matters not whether you have zero properties or hundreds (thousands?). Ask your questions and learn. Set goals. Put it on paper. Don’t have analysis paralysis. I just jumped in at 23. I’m not saying that you should ignore due diligence, but there is a time when you “do or don’t”.

    Follow the lessons of the experienced on this site. No risk (good, informed risk), no reward. In my 20’s, I used to project future net worth and cash-flow. If you are here, you are probably very interested in RE. Soak up the advice whether you are just starting out or have tons of RE. Set some goals for 2014.

    btw – I’m 50 something (told that I look much younger) and RE has been very good to me.

    • That’s great Cheryl! Both that you look younger and that you got started in RE so young. I totally agree with you- get educated and do your due diligence and then jump in. So many people sit around staring at it all for so long the deals fly right by them.

      Enjoy your holidays!


  2. Great Article!

    I have made alot of mistake in relocating to a New State. I have 10 years of experience as a real estate agent and maybe 1 year of real estate investing experience. My first wholesale deal i did I made 20k in profit and i didn’t even know it was a wholesale deal ,or at least i didn’t call it that. This happened back in 2005. This year was full of trial and error. It has actually opened my eyes to focusing more long term as oppose to the immediate cash flow. I will admit, i have beat myself up alot by making so many costly mistakes, but at least I can say I took action and made them and learned from them. I am finding that many people who do real estate investing are actually licensed real estate agents. Many of them struggle to find their identity as an agent or investor. As I reevaluate my business and my life I am understanding the direction i wish to go in. I trust you all do the same.

    Happy Holidays to you All!

    • You too Gerald! That’s hilarious about not knowing you did a wholesale deal. But hey, what works works! I’m with you about immediate income versus the long-term. Sounds like you have a lot of good experience.

      I wish you the best!

  3. Ali –

    I agree completely. This is the time to take an honest look at what worked this year and what didn’t and make changes. It could be that your vision for business has actually changed. If that’s the case then adjust and move on. If you do this evaluation and get your plan together (while drinking your wine) for 2014 instead of just sitting around watching TV (and drinking your wine) you will be leaps and bounds ahead of most other investors. They just won’t go to the trouble. Happy Holidays Ali!


    • You too Sharon! I have a guess as to what your drink of choice will be this holiday… 😉

      I totally agree with you! I would venture to say just about everyone’s plans have to have shifted at least a little in a year. There’s never a for sure way to know exactly what your plan will be and what your results will be over any longer period of time. At a minimum, you had to have learned at least one new thing in this past year that you want to adjust your future plans to.

      Enjoy your holidays Sharon!

  4. I also found this info very helpful, I have completed my 2nd year in business 6 properties 4 Lease Options and 2 sub’s, kept one has rental and sold the other for 15k profit on contract with 3 yr balloon. Wanted to do more, but will work with what makes it self available, all deals are completely 100% leveraged I only do 100% creative deals. Goal this year is to complete a multifamily deal with 100% OPM, and do some more Flips and add some more Lease Options deals. Right now my biggest fear is completing that first multifamily, everybody tells me I can’t find a multifamily deal without any money out of my own pocket, and I know I can find one and close it, that’s what the plan is for 2014, bye the way every thing up to this point as been, part time effort,Starting 2014 we will be putting fourth full time effort, and looking for better results. Reflect and building a game plan to get where I want to be, and take time to set new goals for the new year is very important indeed, thanks for the great article I enjoyed reading and putting it into action.

  5. Michael Walker on

    REFLECT, CONGRATULATE (yourself), and DREAM. What a wonderful way to some up 2013 and prepare for 2014. Ali B., I love how you titled the last section “Start with a Win”. Surviving is definitely a win we all can appreciate. I can’t forget the “Fun Part” either. That’s exactly what I’m looking forward to, “FUN”! Fun investing, Fun with my Family and Fun in Life. Tanks Ali B. for a great article.

    All the Best and More in two-zero-one-four!!!

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