A Parent’s Survival Guide to College Applications

Written By Ryan Stille

August 24, 2026

College Application Season Is Here!

I can’t believe it’s college application season! Our youngest, a senior in high school, started completing the Common App earlier this month. Our middle son has 2 years left before his college graduation as our oldest graduated earlier this summer. We’re beginning to see the light at the end of the tunnel! Here are some tips that have worked for our family that may help yours as you navigate the college selection process.

Start Early and Create a Plan

Start early. There’s a lot of biographical and academic information to input into the Common App. You can always double-check your student’s work before releasing the application to selected colleges. My son and I have a designated appointment each weekend to connect and spend time working through the process. This helps with better communication and an understanding of what’s done and what needs to be done.

I found it valuable to circle a date on the calendar, say mid-October, as a virtual finish line. Then we worked backwards knowing exactly how many weekends are available to huddle up. I use this same approach in serving my clients; setting a date and working backwards. This provides structure as the work gets done at a natural pace without stretching the process out longer than necessary.

Letters of Recommendation Matter

Speaking of work, encourage your student to reach out to those who may provide a letter of recommendation. Asking early and often from teachers, counselor, or a mentor provides space. This also allows you to teach your student the gentle art of follow-up; a key life skill that all young adults need to master. A text, email, or—call me old fashioned—a phone call allows your student to stay engaged with those who volunteered to write a recommendation.

Managing the Essay Process

Essays are necessary but editing my boy’s writing created too much friction in our home. Our solution was to collaborate with a professional who checks in and offers suggestions on their work. The accountability of sharing your writing every other week with another person, not AI or mom and dad, created forward progress with less stress.

I’m a big fan of books and found The Price You Pay for College by Ron Leiber a must read. This book does a great job outlining a road map into what likely will be one of the largest financial decisions you make for your student. I found various perspectives from the college vantage point eye opening and walked away with knowledge. College is a business. Yes, the application process is part of it, but staying at the same school after freshman year is just as important to mom and dad as it is to the university.

Understanding the Cost of College

So how much is this really going to cost? You apply to a bunch of schools, receive acceptances, and then wait for a letter from the financial office to see how much the first year will really cost. Merit based aid, essentially the college saying we like you and want you at our school here’s a discount, is helpful to the bottom line. Typically, you need to keep a certain GPA throughout your stay for the discount to continue. Some universities offer a lot, others not so much. Either way, it’s valuable to have a conversation and plan in place on how you’ll pay for college before sending out applications.

Have the Financial Conversation Before Acceptance Letters Arrive

Talking with your partner/spouse on how you’ll afford this or split costs with your student via loans is critical BEFORE the acceptance arrives. This is all about managing your own expectations as it is managing your students. You shouldn’t let cost dictate where you apply, because who knows how much merit-based aid may arrive. However, you can’t ignore costs entirely. How you’ll choose to pay is personal; a conversation or series of chats before it’s necessary is priceless.

Our Family’s 529 Strategy

For our family it was saving two years of estimated expenses into a 529 savings account and then cash flowing the remaining years. A year or so ago the rules on 529s loosened and you can now transfer any leftover monies from a 529 to your student’s Roth IRA once they are earning income (subject to an annual and lifetime cap). This change in landscape allowed us to top off the 529s so we could remove pressure from future family income.

Why We Used Multiple 529 Accounts

It’s worth noting you can open more than one 529 for your student. I opened 529 accounts for my boys before they were born and funded them aggressively with equities/businesses to hedge the rising cost of education over 18 years. During their high school years, I opened another 529 for each of the boys and put the money in cash, not invested. This worked out well in 2022 when the market tanked, I withdrew from the cash account to pay tuition and expenses, so my equities had time to recover. Currently as company values hit new highs I’m liquidating from the equity 529. Regardless of how the “stock market” plays out, our family isn’t reacting to current events or the tragedy DuJour. This is what planning is all about, acting not reacting.

FAFSA and the CSS Profile

Some universities will require the CSS profile to be completed. Essentially a way for colleges (mostly private) to see where exactly your wealth is before these schools offer merit-based aid. FAFSA hasn’t been helpful to our family or the affluent families we serve given strong household income. Every family is different, if you need to complete these forms based on the colleges your student is attending, get it done before Thanksgiving.

After the Applications Are Submitted

Ok, now what? Once the applications are sent, go out and celebrate that you and your student survived the process! Congratulations! It can be a stressful time for students and parents.

Visiting Admitted Student Days

In the spring, review the acceptances received and invest the time to visit your student’s top three schools on their “admitted Freshman Day”. All colleges put on a big show, inviting all accepted students to “test drive” the college via a campus visit. This provides you and your student with a feel for what campus life, activities, and growing up away from home may be like.

Final Thoughts

In the end, every student will find their place. It’s a lot easier to start and finish at the right college the first time than having to switch universities mid-way through the process. Setting time aside to work with your student and talking through the process makes a positive difference. Good luck!

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