5 Lessons From 5 Years in my Own Business

posted by Andrea | 08/9/2012

I often get emails asking for tips and suggestions on starting a business or a blog. And over my blogging break, I thought a lot about my business — things I love, things I don’t love, things I wish I did differently, and things I wish I would have realized early on.

I’m most definitely not an expert, but since I did grow my business based almost completely on trial and error {I’m not joking} I have learned a few things over these past 5 years — seriously, how has it been FIVE years already!

Anyway, if I were starting all over again {which I hope to never do!} these are a few things I would remind myself of continuously.

1. It takes time — LOTS of time.

I can’t tell you how many times different business mentors told me that I needed to give it at least 5 years before I could consider my business a success or a failure.

FIVE years! Yeah right!

I never thought it would take me the full 5 years because I figured I had tons of energy, drive, and determination. But almost anyone willing to see a business to success also has tons of energy, drive, and determination.

It’s been almost 5 years since I first started my organizing business and 2012 will be the first year that I’ll actually make a good full-time income. The 2 years prior, I made a healthy part-time income. The first 2 years… I fought to break even!

So you better be willing to work hard (really hard) for several years if you really want a fair chance. As long as you love what you’re doing, and you continue to move forward, try not to be discouraged if things don’t work out right away.

That said, I’d also encourage you NOT to quit your day-job. 

If you currently work full-time or part-time, see if you can “get your feet wet” in your new business start-up before you stop the cash-flow from your current line of work. The main reason I allowed myself to work so many hours for so little money those first 2 years was because I was still working full time. I gradually continued to cut back my day job hours until I was only working about 1 day a week on top of my business.

Obviously, that’s not possible in every situation, but the steady income from my day job definitely helped me to justify the lack of income from my business.

2. It’s not always glamorous. 

Just because you own the business doesn’t mean you get to sit around and do nothing. It usually means you have to do everything — especially in the beginning.

It means you have to do all the non-glamour jobs like contacting clients to get their money when they “forget” to pay, finding advertisers/sponsors, working nights and weekends, sacrificing vacation time {or at least paid vacation time}, and wearing WAY too many hats at one time!

However, as I’ve blogged about before, there are plenty of positive rewards that counter these sometimes negative and unglamorous jobs, so it usually works out OK in the end.

3.  People will think you’re weird.

If you get out of bed one day and start telling people you’re starting a business… they WILL think you are weird. Some of them will act like your ideas are stupid… but that’s because they are jealous. Others will think you’re weird just because starting a business is definitely a little weird.

You need to be OK with this. If you’re the type of person who constantly seeks approval from others, don’t start a business. It won’t be pretty!

I can remember when I told my dad {an extremely entrepreneurial man} that I was thinking of starting a business. He looked at me and immediately said, “don’t quit your day job!”

Thanks Dad! 🙂

As I mentioned above, I was fortunate that I didn’t have to quit my day job; but I was also so self-conscious about telling people I was “starting a business” that I waited to tell most of our family and friends until I had a handful of clients and a stack of business cards.

They still thought I was weird, but at least I had a tiny amount of success to propel me forward.

4. A closed door = an open window.

You just need to find that window!

If you’re wondering what the heck I’m talking about, I’m just trying to say that there’s a decent chance you will fail… and that’s OK. In my experience, every closed door has eventually lead to an open window of opportunity.

I failed many times and I will continue to fail. Some are small fails, some are larger {and more costly} fails. But I learned and grew with each failed attempt, and my business would not be where it is today if I was always handed everything on a silver platter or told what to do every step of the way.

If it wasn’t for one of my failures, I would have never ventured into the blogging world {which eventually led me to becoming a Virtual Assistant} — and now I make about 90% of my income from blogging and VA work. Talk about one BIG OPEN WINDOW! 

I wanted to quit SOOOOO many times the first few years. And if I’m totally honest, there are still times when I question if it’s all really worth it. Thankfully those times are fewer and far-between. Now that I have Nora, I’m so thankful I pushed through all my failures and can now have the flexibility of working my job around my family.

5. It’s only worth it IF you love it!

If you really, truly love what you do, then it will be worth all the time, money, and energy you put into building your business because you’ll end up with a “career” that you love, not just a “job” that you do.

However, if you don’t love what you do {even if you used to love it}, just stop. Or at least take a step back.

Your business will not be successful unless you are passionate about what you’re doing… not to mention you’ll be really grumpy.  Of course, there might come a time when you’re running your business only for the money {which I totally understand} but that’s not a great solution for long-term success.

If you feel like you’re in a slump, over-tired, over-worked, and not loving your business — this could be the time to look for an open window. That window might be a new angle for your business, a totally different business, going back to the cooperate world, staying home with your family, or doing volunteer work —  but you’ll never know until you start looking!

My intention in writing this post is to be realistic, but still inspirational for anyone trying to start up a business. Obviously, I’d love to just focus on the positives… but if you know me in real life, you know that I just “say it how it is” and I’ll be honest — there are days, weeks, and months when running a business and being your own boss is really crappy.

It’s hard, it’s not always fun, and I’m honestly not sure I could have lasted those first years if I had the stress of a new baby on top of everything else.

Starting a business {big or small} is not for everyone. However, if you’ve ever had even the tiniest dream about starting your own business, I’d encourage you to continue dreaming… and hopefully this post will give you a little more to think about!

Filed under: WorkBusiness 101VA Work

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  1. Carolyn Thomas



    Will I agree with you and I am working and doing craft shows and put one together for the PTO and they loved it and we are thinking of doing it again next year.
    I told the ones that was the first time doing it that when you get your booth rent back for the first time you are doing good….I did 5 craft show before I made my booth rent and more…The first one that I did…i miss getting my booth rent by $1, Then the next one I did I got my booth rent and a couple dollars over….It was like that till the 6th one….So now I just keep going and doing and found out things that will sell and things that will not…but I keep going…I got ask to do 3 back to back shows, so I think I am going up in the world…lol…So keep the faith and go for your dream.


  2. Alexandria Snider


    I found your blog while searching what people use for their planners and one woman was using your “top 5” list. I loved it, so I had to come check it out. I love your blog even more!

    I LOVE organizing and would love to become a professional organizer! Can you point me in a direction of where to start?

    I do have experience running a business. I have a direct sales business, and my mother-in-law started a party rental business a year ago, which is starting to take off. While I enjoy both these businesses, they aren’t my passion. I would organize for people for free, so if I ould do it and get paid, that would be the most awesome thing ever.

    Oh, and I am a SAHM of four boys and my husband travels a lot for work (only home every other weekend), so having a business that I could work around my boys’ schedules would be great!

    Thank you so much! I look forward to your response!


    Andrea Reply:

    Hi Alexandria,
    If you have some specific questions, feel free to email me {andrea@andreadekker.com}. However if you just want to talk through some stuff, we can certainly set up a coaching appointment.


  3. Pamela


    This post inspires me to continue to dream, grow, and post…. Thank you, I needed that kick-start again..


  4. Cathy


    I am a small business owner (my first business just celebrated our 7th anniversary and I also consult for other small business owners). I completely agree with your assessments!
    Especially the 5 year timeline – I would say that is very accurate!

    Over the first five years I often wondered if I knew then what I knew NOW, would I do this again? – but now sitting from a 7 year perspective I am proud of where I am. I made a lot of sacrifices to get here.

    But like you say – you need to LOVE what you are doing, have a side job if possible, and when one door closes another opens (I have started a second business due to opportunities presented from my first).

    Congratulations on your success. And thank you for giving me lots of interesting tools and tips that I use everyday in business and at home!


  5. Erica


    Excellent post – I’ve always subscribed to the philosophy that you never fail until you stop trying, so good for you for pressing on!


  6. Jill Flory


    My sister sent me a link to this post. I needed to read it! I’m in the first months of my own business and it can get overwhelming at times! I needed to read this post today – thanks so much for writing it!


  7. Hilda


    Thank you so much for this post! I’ve been thinking of becoming a professional organizer and have been trying to think through the pros and cons and weigh out my best options and plans. Your honesty and journey has helped a lot. Thanks!


  8. Doreen@househoneys


    As always, your advice is spot on. I started a residential cleaning business on my own in 1999. Currently, my husband and manager run the day to day operations, which I’m extremely grateful for because it gives me the opportunity to spend time on what I love…my blog :). Some people just don’t get it when it comes to making money and being successful. One of my favorite sayings is ‘if it was easy, everyone would do it and then no one would make money’. I started my blog in April, spend about 2-4 hours a day on it, and only have about 45 likes on FB and maybe 20 followers. Yes, I would love that to change, but if it doesn’t, I’ll just keep on keepin’ on because I love it. I’m not in it for the money, which is why I know I’m in the right place.

    I thought about writing a post about the same thing! Guess I’ll wait a bit so I won’t look like a copy cat ;).


  9. Melissa


    Thanks. This was a really good post especially when I am at a point in my life when I need it. I am trying to start my own business, but it is definitely hard when I am also working almost full-time at my own job and trying to keep up with my family of 4, which includes one 4 year old and one 1 year old! Thanks for the kind words and the inspiration to keep on going!


  10. kalynbrooke


    No one wants to hear it takes time, but it’s so true!!! Thanks for sticking it out and being a role model for the rest of us. 🙂


  11. Nasreen Fynewever


    A heartfelt thanks for sharing your journey. Best wishes for the future.